We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals nearby Weisinger Family Winery

3150 Siskiyou Blvd, Ashland, Oregon 97520-9142
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    ₹ 17,591 Average
    |||
    |||
    ₹ 0₹ 72,000+
    Suitability
    More filters
    Travellers to Ashland are booking June dates now. Secure your holiday home today, and have the perfect trip.
    All 72 Rentals in Ashland
    6.0 kilometres from Weisinger Family Winery
    7 Bedrooms, 6 Bathrooms, Sleeps 15 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    5.0 kilometres from Weisinger Family Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    5.6 kilometres from Weisinger Family Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    5.0 kilometres from Weisinger Family Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Parking
    • Air Conditioning
    • Mountain Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and enjoy your stay in this classic, fully restored farmhouse built in 1890. You’ll pass local coffeehouses, boutique shopping, and fantastic restaurants when you stroll just four short blocks to the Oregon Shakespeare Festival theatres. Furnished with an artistic blend of modern farmhouse...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Make Enquiry
    4.9 kilometres from Weisinger Family Winery
    7 Bedrooms, 7 Bathrooms, Sleeps 13 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Hot Tub
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Anne Hathaway House was built in 1908 as a boarding house for travelers. David and Deedie Runkel purchased the home in 2002 and continue to operate it today. Located just four short blocks from the Oregon Shakespeare Festival, the Anne Hathaway House is ideal for large groups of theater goers,...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 13
    Make Enquiry
    5.8 kilometres from Weisinger Family Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, Water Suite Cottage is one of the closest properties to OSF, just one and half blocks to the Theaters. The home features a kitchenette, living room with sofa-bed, flat panel 4K TV, one...
    View all property information
    Location Information
    Ashland, Oregon
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    5.2 kilometres from Weisinger Family Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3rd Night Free!!! November 5th through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply The Historic '1900' House is the best of Downtown Ashland... and less than five blocks to the renowned Oregon Shakespeare Festival. A quiet residential neighborhood, our home...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    5.6 kilometres from Weisinger Family Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully renovated - available May 2018 It doesn’t get closer to OSF than this! Enjoy a relaxing getaway at the Pioneer House. Originally built in 1904, this historic home is one one of three located on the property. Just one block from the theatre, you’ll also have easy access to dining, wine...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    5.6 kilometres from Weisinger Family Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It doesn’t get closer to OSF than this! Enjoy a relaxing getaway at the Pioneer House. Built in 2008, this home is adjacent to a historic home and one one of three located on the property. Just one block from the theatre, you’ll also have easy access to dining, wine tasting, and shopping. Private,...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    5.2 kilometres from Weisinger Family Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3rd Night Free!!! November 5th through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply The Historic '1900' House is the best of Downtown Ashland... and less than five blocks to the renowned Oregon Shakespeare Festival. A quiet residential neighborhood, our home...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Save time - get the best Ashland rentals sent straight to your email!
    Get the List
    6.5 kilometres from Weisinger Family Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated, and just five blocks from Downtown Ashland and the Oregon Shakespeare Festival! This cottage has two private bedrooms, with a queen bed in each. The bathroom has an oversize walk-in shower, great for those with physical limitations. The common area features a 32' flat panel...
    View all property information
    Location Information
    Ashland, Oregon
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    5.0 kilometres from Weisinger Family Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Parking
    • Balcony
    • Private Garden
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
    View all property information
    Location Information
    Ashland, Oregon
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    5.0 kilometres from Weisinger Family Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    • Washer
    • Mountain Views
    • Terrace
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sleeps 6 - Tesla Charging Station Relax and enjoy your stay in this classic, fully restored farmhouse built in 1890. You’ll pass local coffeehouses, boutique shopping, and fantastic restaurants when you stroll just four short blocks to the Oregon Shakespeare Festival theatres. Furnished with an...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    5.7 kilometres from Weisinger Family Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, Oak Tower Cottage is one of the closest properties to the famed Oregon Shakespeare Festival, and just one and half blocks to the Theaters. The home features a full kitchen, a patio, two...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    5.0 kilometres from Weisinger Family Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Terrace
    • Washer
    • Wi-Fi
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
    View all property information
    Location Information
    Ashland, Oregon
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    5.0 kilometres from Weisinger Family Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Washer
    • Air Conditioning
    • Private Garden
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
    View all property information
    Location Information
    Ashland, Oregon
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    5.2 kilometres from Weisinger Family Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3rd Night Free!!! November 5th through April 30th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply This home is brand new to the vacation rental market and is everything a family or small group is looking for. Close to restaurants and retailers... and less than five blocks...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    6.5 kilometres from Weisinger Family Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated, and just five blocks from Downtown Ashland and the Oregon Shakespeare Festival! This cottage has two private bedrooms, with a queen bed in each. The bathroom has an oversize walk-in shower, great for those with physical limitations. The common area features a 32' flat panel...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    5.7 kilometres from Weisinger Family Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    (NOTE: Listed through the City of Ashland as Oak Street Cottages) Built in the late 1800's, the Sherwin House is in the heart of Ashland and is one of the closest properties to OSF, just one and half blocks to the Theaters. The home features a full kitchen, a front yard with seating, two private...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 11
    Make Enquiry
    8.0 kilometres from Weisinger Family Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    High above the hamlet of Ashland sits Bel Canto, a quiet home nestled in the hillside with stunning views of the charming town below. This immaculate space is situated on the lower level of the owner's home with private entry. Although you’ll feel a million miles away in this peaceful sanctuary,...
    View all property information
    Location Information
    Ashland, Oregon
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    List your property for free!
    List your holiday home where TripAdvisor travellers can find it.
    Add a Listing
    6.0 kilometres from Weisinger Family Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Blue Moon Cottage is attached to the main home but has two private entrances. It offers a full kitchen, a gas fireplace, air conditioning, a separate bedroom with a comfy queen bed, a full bath with shower/tub combination and a private patio. There is also a flat screen television in the living...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    5.0 kilometres from Weisinger Family Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Private Garden
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
    View all property information
    Location Information
    Ashland, Oregon
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    5.7 kilometres from Weisinger Family Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, Oak Lawn Cottage is one of the closest properties to OSF, just one and half blocks to the Theaters. The home features a full kitchen, living room with fireplace, flat panel TV, a patio, two...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    5.0 kilometres from Weisinger Family Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Air Conditioning
    • Patio
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax and enjoy your stay in this classic, fully restored farmhouse built in 1890. You’ll pass local coffeehouses, boutique shopping, and fantastic restaurants when you stroll just four short blocks to the Oregon Shakespeare Festival theatres. Furnished with an artistic blend of modern farmhouse...
    View all property information
    Location Information
    Ashland, Oregon
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    5.7 kilometres from Weisinger Family Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    (NOTE: Listed through the City of Ashland as Oak Street Cottages) Located in the heart of Downtown Ashland, these cottages are one of the closest properties to OSF, just one and half blocks to the Theaters. The home features a full kitchen, large living room with fireplace, flat panel TV, patio,...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    6.7 kilometres from Weisinger Family Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Park-like setting, high above Ashland, yet very close to town Tucked away in a canyon filled with Aspen and Pine trees, this quiet retreat is conveniently located just a five-minute drive from downtown Ashland. Guests have access to the grounds which are located in a well-maintained, park-like...
    View all property information
    Location Information
    Ashland, Oregon
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    6.0 kilometres from Weisinger Family Winery
    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just five blocks from the Oregon Shakespeare Festival in a historic Ashland neighborhood... Built in the early 1900's and fully renovated the Blue Moon House has it all! Five bedrooms, each with it's own private bathroom. A gourmet kitchen with a large dining area, a living area with a...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 11
    Make Enquiry
    5.0 kilometres from Weisinger Family Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Washer
    • Parking
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
    View all property information
    Location Information
    Ashland, Oregon
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    5.0 kilometres from Weisinger Family Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Private Garden
    • Balcony
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
    View all property information
    Location Information
    Ashland, Oregon
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    6.7 kilometres from Weisinger Family Winery
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Parking
    • Wi-Fi
    • Patio
    • Balcony
    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Park-like setting, high above Ashland, yet very close to town Tucked away in a canyon filled with Aspen and Pine trees, this quiet retreat is conveniently located just a five-minute drive from downtown Ashland. Guests have access to the grounds which are located in a well-maintained, park-like...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
    Make Enquiry
    5.0 kilometres from Weisinger Family Winery
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Private Garden
    • Air Conditioning
    • Parking
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on Russell Street in Ashland, the corporate and vacation rentals at Falcon Heights provide easy access to the Railroad District as well as vibrant downtown shopping, dining, and theatre. Take a short stroll on the walking path out the back door and you’re there! These sleek, stylish...
    View all property information
    Location Information
    Ashland, Oregon
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    4.8 kilometres from Weisinger Family Winery
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3rd Night Free!!! November 5th through February 28th Black-Out Dates Apply on Holiday Weeks Other restrictions may apply Light, bright and simply gorgeous, this charming studio is just a ten-minute walk from the Festival downtown and is the perfect place to enjoy Southern Oregon at any time of...
    View all property information
    Location Information
    Ashland, Oregon
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    6.5 kilometres from Weisinger Family Winery
    Studio, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PRIVATE ENTRY AND PARKING The single, private bedroom has a queen bed and private bathroom with shower. Flat-panel TV, with free cable and wi-fi. A mini-fridge, and microwave are also available for your comfort. The courtyard is beautifully furnished and has a beautiful shared secret garden for...
    View all property information
    Location Information
    Ashland, Oregon
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    The High Street Cottage An Artists' Garden Cottage1 / 10
    (7)Excellent
    6.4 kilometres from Weisinger Family Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Porch
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 March 2018
    The columnist Herb Caen wrote of the San Franciscan native who died and went to Heaven. Saint Peter met him at the Pearly Gates and gave him a tour of his new eternal home. When...
    Reviewed 4 March 2016
    My boyfriend and I did "experience" gifts for each other at Christmas and this was mine to him. We loved it! Fantastic craftsman cottage with all the amenities you need...
    See all reviews
    About this property
    Set in Ashland's best neighborhood, this 1931 cottage has been lovingly restored and set up to address your every need. Cozy and incredibly clean, filled with art, hand-made pottery, antiques and hand crafted furniture. Comfortable beds, high quality linens and a fully equipped kitchen. A truly...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    The Terra Cottage Inn a beautiful Luxury Apartment1 / 10
    (10)Excellent
    6.5 kilometres from Weisinger Family Winery
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Mountain Views
    • Cable/satellite TV
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 2013
    Terra Cotta Cottage is a beautiful place to stay in Ashland. Every need has been anticipated with artistic thoughtfulness.Staying there was an experience in itself. From the koi...
    Reviewed 12 April 2013
    We thoroughly enjoyed our stay in Terra Cottage Inn. The space was perfect for our family of four with two young children. The beds were comfy for everyone. The whole...
    See all reviews
    About this property
    Nestled into one of Ashland's best neighborhoods, the Terra Cottage Inn is a clean and beautiful, hand-crafted artists' cottage. Full of art, hand thrown pottery, custom built furniture and all the amenities to make this a true luxury experience. Quality comfortable beds with high thread count...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Abigail's Cottage, 10-min. walk to plaza/theaters1 / 20
    (7)Excellent
    6.5 kilometres from Weisinger Family Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Secure Parking
    • Outdoor Dining Area
    • Air Conditioning
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 September 2015
    Beautiful spot, wonderful cottage, perfect for the four of us. Less than a 5 minute drive to down town Ashland with it's fabulous plays, restaurants and shopping. Lovely new...
    Reviewed 6 May 2015
    Abigail's has new owners, who we found to be friendly and helpful. Super clean cottage, walked to plays two times a day. Great time
    See all reviews
    About this property
    Abigail's Cottage within walking distance to the city center, is licensed by the city of Ashland (Business License #007411 & Planning Action #06-275) and Jackson County, (#1581566C) and meets required health, safety and fire codes. Comfortable two bedroom 1 1/2 bath cottage, completely renovated...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2nd Street Cottages, HERITAGE HOUSE1 / 16
    (6)Excellent
    5.3 kilometres from Weisinger Family Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Balcony
    • Private Garden
    • Air Conditioning
    • DVD Player
    • Terrace
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    I have stayed at 2nd Street Cottages before and it continues to be our favorite vacation rental in Ashland. Such a well kept and beautiful Cottage. The owner pays such great...
    Reviewed 16 April 2017
    I would go back to Ashland just to stay here. Seriously. We were passing through on our way to California and needed somewhere tho spend the night. What a lucky accident! The...
    See all reviews
    About this property
    THE HERITAGE SUITE IS A DELIGHTFUL 4 BEDROOM, 3 FULL BATH COTTAGE THAT ACCOMMODATES 8 GUESTS COMFORTABLY. Second Street Cottages is located on a quiet side street in the historic and beautiful Railroad District. Built in 1900, this home has been lovingly restored with great attention to detail...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Walk to Downtown/Theaters from this Charming Home1 / 8
    (1)Excellent
    5.3 kilometres from Weisinger Family Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 July 2018
    The location was terrific and close to downtown but very quiet and peaceful. The home was lovely, well done and plenty of space for our group. We loved the porch!!! All the...
    See all reviews
    About this property
    Welcome to the Victorian Rose at Blossom View Cottages. We are located in the historic railroad district, less than half a mile from theaters, Plaza and Downtown. Let this charming, historic home fill you with a sense of well-being and luxury. There are two bedrooms, each with a queen bed, and a...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    5.3 kilometres from Weisinger Family Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the Blue Hyacinth in Blossom View Cottages. Walk to downtown and OSF or sit back and relax at the Blue Hyacinth, part of Blossom View Cottages. This is a luxurious and comfortable home in Ashland's historic railroad district. Downtown Ashland, the theaters, and galleries on A-Street are...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Enquiry
    Carlisle Garden Suites - Calla Suite1 / 16
    (1)Excellent
    4.9 kilometres from Weisinger Family Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Carlisle Inn and Suites is a wonderful place to stay in Ashland. It’s centrally located to downtown and the theatres. The units are all adorable and newly remodeled. The staff...
    See all reviews
    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Stay Ashland like never before.  Explore days, campfire stars at night!1 / 13
    (3)Excellent
    2.7 kilometres from Weisinger Family Winery
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 July 2018
    Anyone in this area needing to rent a trailer should go with this company. They are wonderful. Their trailers are emmaculate and come with everything you need. They went out of...
    Reviewed 15 May 2018
    I loved driving into the campground and finding the trailer and campsite all set up and waiting for us. The trailer was super clean and well stocked with bathroom and kitchen...
    See all reviews
    About this property
    Vacation rental. RV Adventure. You choose favorite RV site in So. Oregon! Trailer camping is where tiny house intersects with camping; the perfect relaxing balance of re-energizing in the great outdoors and snuggling up in cozy cottage comfort! Rent a sweet recreational trailer delivered to the...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    2nd Street Cottages, GARDEN SUITE1 / 11
    (5)Excellent
    5.3 kilometres from Weisinger Family Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Terrace
    • Central Heating
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 March 2017
    My wife and I stayed in the small apartment on the second floor for a few nights. Sugar met us when we arrived and made the whole transaction very simple for us. The room was...
    Reviewed 23 June 2016
    Lovely cottage with tons of character located in downtown Ashland. We walked just a couple of short blocks to the theater and restaurants. Ours was a spacious, upstairs room...
    See all reviews
    About this property
    THE GARDEN SUITE IS A CHARMING TWO BEDROOM, 2 FULL BATH COTTAGE THAT COMFORTABLY WELCOMES 5 GUESTS. Second Street Cottages is located on a quiet side street in the historic and beautiful Railroad District. Built in 1900, this home has been lovingly restored with great attention to detail and has...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    Pelton Villa1 / 12
    (1)Excellent
    5.4 kilometres from Weisinger Family Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Washer
    • Parking
    • Private Garden
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2018
    Our family of 4 stayed 2 nights in the Earth Suite because everything else was booked. We would've stayed 3 if it had been available. We walked to OSF, downtown for meals, and...
    See all reviews
    About this property
    Experience Ashland like a local. Pelton Vacation Rental in downtown Ashland is the place to be. We have 3 private units: The Villa main house, Earth suite carriage house, and Water suite carriage house. As a vacation rental, other than having the best location in Ashland, we offer our guests...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    5.3 kilometres from Weisinger Family Winery
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Balcony
    • Mountain Views
    • Internet Access
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Second Spring Property We are excited to announce that our property was given The Ashland Historic Preservation Award in 2014. This luxury vacation property is uniquely designed for elegance and comfort that will make you feel right at home. This newly renovated craftsman can be rented as a 3...
    View all property information
    Location Information
    Ashland, Oregon
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    4.9 kilometres from Weisinger Family Winery
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    2.7 kilometres from Weisinger Family Winery
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Washer
    • Patio
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This house is located on our ranch. It is 5 miles from downtown Ashland. It is 3 miles to local airport & 3.5 miles to local golf course. The views of the mountains, pastures, wildlife, cows & horses are very beautiful. It is relaxing and enjoyable. This home has hardwood floors. It is a...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    Make Enquiry
    Perfect vacation cottage1 / 25
    (2)Excellent
    6.0 kilometres from Weisinger Family Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2016
    Perfectly furnished for our party of four adults; perfectly stocked kitchen; perfect front yard for dining al fresco and watching deer go by; perfect neighborhood for daily...
    Reviewed 25 August 2015
    Great location for walking to theatres as well as restaurantsand shopping in Ashland. Great space for two couples tobe separate or to be together. Front porch is a...
    See all reviews
    About this property
    Fully restored vintage cottage in a quiet neighborhood just steps away from downtown Ashland and the theater. Surrounded by lovely gardens assuring a private and serene environment. The cottage is tastefully decorated , is immaculate and has 2 bedrooms, 2 baths, office, full kitchen, front porch...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    5.3 kilometres from Weisinger Family Winery
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Second Spring Property We are excited to announce that our property was given The Ashland Historic Preservation Award in 2014. This luxury vacation property is uniquely designed for elegance and comfort that will make you feel right at home. This newly renovated craftsman can be rented as a 3...
    View all property information
    Location Information
    Ashland, Oregon
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    6.6 kilometres from Weisinger Family Winery
    Studio, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just a stone's throw to the plaza, a licensed one-bedroom vacation rental suite is tucked behind one of Ashland's charming craftsman-style bungalows. Your private gated entrance, located behind the house, opens onto a peaceful garden and quaint patio - a wonderful place to enjoy morning coffee and...
    View all property information
    Location Information
    Ashland, Oregon
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Make Enquiry
    4.9 kilometres from Weisinger Family Winery
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nine luxury cottages and suites surround an exquisite tranquil garden. All units have private entrances, kitchenettes, luxury baths, free WI-FI, A/C and ceiling fans, morning pastries and coffee, and free parking. Queen and King bed units, some with additional daybeds. All king suites can be...
    View all property information
    Location Information
    Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    1
    List your property
    Owner log in