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Holiday Rentals nearby Oregon Shakespeare Festival

15 S Pioneer St, Ashland, Oregon 97520-2749
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    Travellers to Ashland are booking November dates now. Secure your holiday home today, and have the perfect trip.
    All 71 Rentals in Ashland
    1.0 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    0.7 kilometres from Oregon Shakespeare Festival
    7 Bedrooms, 6 Bathrooms, Sleeps 15 Quick View
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    The Terra Cottage Inn a beautiful Luxury Apartment1 / 10
    (10)Excellent
    0.9 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Walk to Downtown/Theaters from this Charming Home1 / 8
    (1)Excellent
    0.5 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • 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...
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    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...
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    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    The High Street Cottage An Artists' Garden Cottage1 / 10
    (7)Excellent
    0.8 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • 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...
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    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...
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    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Abigail's Cottage, 10-min. walk to plaza/theaters1 / 20
    (7)Excellent
    1.0 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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
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    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...
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    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.5 kilometres from Oregon Shakespeare Festival
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
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    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...
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    Ashland, Oregon
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    2nd Street Cottages, HERITAGE HOUSE1 / 16
    (5)Excellent
    0.3 kilometres from Oregon Shakespeare Festival
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Balcony
    • Private Garden
    • Air Conditioning
    • DVD Player
    • Terrace
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 12 November 2016
    Just enjoyed 5 nights at the 2nd Street Cottages. Everything was perfect. We flew in from the east coast and got in close to midnight but Sugar was there to greet us. She...
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    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...
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    Ashland, Oregon
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.7 kilometres from Oregon Shakespeare Festival
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Private Garden
    • Air Conditioning
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    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...
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    Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1.0 kilometres from Oregon Shakespeare Festival
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Private Garden
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    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...
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    Ashland, Oregon
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    1.0 kilometres from Oregon Shakespeare Festival
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • 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...
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    Ashland, Oregon
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.6 kilometres from Oregon Shakespeare Festival
    7 Bedrooms, 7 Bathrooms, Sleeps 13 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Hot Tub
    • Washer
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    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,...
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    Ashland, Oregon
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 13
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    0.2 kilometres from Oregon Shakespeare Festival
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    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...
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    Ashland, Oregon
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1.0 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • 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...
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    Ashland, Oregon
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.6 kilometres from Oregon Shakespeare Festival
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • 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...
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    Ashland, Oregon
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    0.7 kilometres from Oregon Shakespeare Festival
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • 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...
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    Location Information
    Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    0.2 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Washer
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Terrace
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully renovated - available May 1st, 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...
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    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3.5 kilometres from Oregon Shakespeare Festival
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the east Ashland countryside, and exactly three miles from the downtown Ashland Plaza and infamous Oregon Shakespeare Festival, this cottage has it all! The mountain views are stunning and the gardens alive with color in the spring and summer. Enjoy the whimsy and art found in the...
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    Ashland, Oregon
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.2 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
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    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...
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    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    1.0 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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...
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    Location Information
    Ashland, Oregon
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.2 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    • Air Conditioning
    • Grill
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    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...
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    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 11
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    Perfect vacation cottage1 / 25
    (2)Excellent
    0.5 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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...
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    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...
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    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.4 kilometres from Oregon Shakespeare Festival
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 and cottage feature a total of four bedrooms, three bathrooms, two complete kitchens, laundry room, and comfortable living...
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    Ashland, Oregon
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    1.0 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • 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...
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    Ashland, Oregon
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1.0 kilometres from Oregon Shakespeare Festival
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • 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...
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    Location Information
    Ashland, Oregon
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Pelton Villa1 / 12
    (1)Excellent
    0.3 kilometres from Oregon Shakespeare Festival
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • 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...
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    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...
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    Ashland, Oregon
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.2 kilometres from Oregon Shakespeare Festival
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    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,...
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    Location Information
    Ashland, Oregon
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.3 kilometres from Oregon Shakespeare Festival
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • 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...
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    Ashland, Oregon
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Carlisle Garden Suites - Viola Suite1 / 14
    (1)Very good
    0.7 kilometres from Oregon Shakespeare Festival
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 April 2018
    We just spent one night here, but wish we could have stayed longer. It was a lovely spot, 4 blocks from down town Ashland. We stayed in the Camomile Suite, which had a king bed...
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    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...
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    Location Information
    Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1.0 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • 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...
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    Location Information
    Ashland, Oregon
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    0.6 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • 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...
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    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.2 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • 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...
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    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1.0 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    • Private Garden
    • Terrace
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    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...
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    Ashland, Oregon
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.4 kilometres from Oregon Shakespeare Festival
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    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 features three bedrooms, two full bathrooms, a complete kitchen, laundry room, and comfortable living room (with a sofa...
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    Ashland, Oregon
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.3 kilometres from Oregon Shakespeare Festival
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    (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...
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    Ashland, Oregon
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    7.7 kilometres from Oregon Shakespeare Festival
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • 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...
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    Ashland, Oregon
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    1.0 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    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...
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    Location Information
    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.3 kilometres from Oregon Shakespeare Festival
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    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...
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    Location Information
    Ashland, Oregon
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    0.4 kilometres from Oregon Shakespeare Festival
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    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 to the OSF. In a quiet neighborhood, our home features a bedroom with a king bed, a bathroom (shower), a full kitchen and...
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    Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3.8 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    A working family farm just 5 minutes from downtown Ashland. Views of mountains can be enjoyed from YOUR private deck, with (seasonal) hops, grapes and blackberries growing right outside. This suite is bright and comfortable, with private entrance. It includes a Master Bedroom (queen bed), a...
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    Ashland, Oregon
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    0.7 kilometres from Oregon Shakespeare Festival
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    A high queen bed dominates the space, which gets diffused light from a skylight and windows on three sides. A spacious bathroom features a clawfoot tub, a separate tiled shower, stained glass window and another wonderful skylight. The Carlisle Garden Suites has 9 unique rooms in three buildings...
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    Location Information
    Ashland, Oregon
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    0.8 kilometres from Oregon Shakespeare Festival
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 year. Tucked into a quiet neighborhood in the Historic Railroad District, this brand new guest house will make you smile....
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    Location Information
    Ashland, Oregon
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2.3 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    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,...
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    Location Information
    Ashland, Oregon
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.7 kilometres from Oregon Shakespeare Festival
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Private Garden
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    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...
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    Location Information
    Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    0.7 kilometres from Oregon Shakespeare Festival
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
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    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...
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    Location Information
    Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    0.7 kilometres from Oregon Shakespeare Festival
    5 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
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    • Wi-Fi
    • Air Conditioning
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    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...
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    Ashland, Oregon
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 11
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    0.3 kilometres from Oregon Shakespeare Festival
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Garden
    • Parking
    • Internet Access
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful, historic, fully renovated home with four bedrooms, three full baths and a fabulous welcoming front porch. Can be rented with Garden Suite, a 2 bedroom, 2 full bath house that sleeps five. Perfect location for your visit to Ashland. Historic Railroad District is situated between two...
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    Ashland, Oregon
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1.0 kilometres from Oregon Shakespeare Festival
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    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...
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    Location Information
    Ashland, Oregon
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    0.7 kilometres from Oregon Shakespeare Festival
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Private Garden
    • Air Conditioning
    • Wi-Fi
    • 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...
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    Location Information
    Ashland, Oregon
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    0.6 kilometres from Oregon Shakespeare Festival
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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...
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    Location Information
    Ashland, Oregon
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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