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 in Ossipee, NH

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    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}
    List your property
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 21 Rentals in the Ossipee Area
    loading...
    From
    ₹9,567
    / Night
    Payment Protection
    View Details
    1 / 11
    5 of 5 stars (3) Excellent
    Ossipee
    3 Bedrooms / 3 Bathrooms / Sleeps 9
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    From
    ₹22,323
    / Night
    Payment Protection
    View Details
    1 / 12
    Ossipee
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
    Overview Make Enquiry
    From
    ₹20,728
    / Night
    Payment Protection
    View Details
    1 / 10
    Ossipee
    5 Bedrooms / 1 Bathroom / Sleeps 10
    traveller have booked this property
    Overview Make Enquiry
    From
    ₹8,291
    / Night
    Payment Protection
    View Details
    1 / 29
    Ossipee
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Very comfortable 3 bedroom, 2 level vacation home located in Eidelweiss resort/Madison, NH on secluded wooded lot. Walking distance to beach and children's playground. Located just 8 miles from the center of North Conway ski area and all the shopping outlets as well as many hiking trails. First... View all property information
    Make Enquiry
    Location Information
    Ossipee, New Hampshire 03849
    From
    ₹12,756
    / Night
    Payment Protection
    View Details
    1 / 20
    Ossipee
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Internet Access
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    4 Bedroom, 2 full bath - raised ranch available for weekly vacation rental with private beach access on Ossipee Lake and Pine Landing Beach Club. (8 min. drive) Large eat-in kitchen with seating and dining area adjacent to kitchen. Large family room downstairs for entertainment. Washer/Dryer... View all property information
    Make Enquiry
    Location Information
    Ossipee, New Hampshire 03890
    From
    ₹127,559
    / Week
    Payment Protection
    View Details
    1 / 9
    Ossipee
    3 Bedrooms / 1 Bathroom / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Located on a 600 feet of waterfront on the Bearcamp River in West Ossipee New Hampshire. Centrally located 25 minutes south of North Conway. House is on a bucolic setting that is like a Norman Rockwell painting. Available for use are kayaks, canoes, lifejacket, fishing pole & a water trampoline.... View all property information
    Make Enquiry
    Location Information
    Ossipee, New Hampshire 03890

    The following rentals are within 10 kilometres of Ossipee, New Hampshire.

    From
    ₹10,779
    / Night
    Payment Protection
    View Details
    1 / 25
    4.5 of 5 stars (7) Very good
    Wolfeboro
    2 Bedrooms / 2 Bathrooms / Sleeps 7
    traveller have booked this property
    Overview Reviews (7) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Fireplace
    • Grill
    • Gym
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    (Please see all 9 of our cottages at CottagesNH.com (our Facebook page). Return to Simplicity. Nine freshly updated Retro 40’s classic Cottages tucked away in the Quaint Lakeside Hamlet of Wolfeboro Falls, the oldest summer resort in America! Your screen door is unlocked and your Cottage keys... View all property information
    Make Enquiry
    Location Information
    Wolfeboro, New Hampshire 03894
    4 of 5 stars Reviewed 17 September 2014
    This is everything Dave says it is! Quiet, cozy, family oriented cabins are well appointed & each has a privacy screen to make you feel separate, yet part of it all, too. A...
    5 of 5 stars Reviewed 21 July 2014
    Having spent a good amount of time throughout college in the Wolfeboro area I was excited to come and stay at the cottages. If you are looking for an opportunity to spend family...
    See all reviews
    From
    ₹9,503
    / Night
    Payment Protection
    View Details
    1 / 22
    5 of 5 stars (6) Excellent
    Wolfeboro
    1 Bedroom / 1 Bathroom / Sleeps 5
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    (Please see all 9 of our cottages at CottagesNH.com (our Facebook page). Return to Simplicity. Nine freshly updated Retro 40’s classic Cottages tucked away in the Quaint Lakeside Hamlet of Wolfeboro Falls, the oldest summer resort in America! Your screen door is unlocked and your Cottage keys... View all property information
    Make Enquiry
    Location Information
    Wolfeboro, New Hampshire 03894
    5 of 5 stars Reviewed 18 July 2014
    We stayed five days in a cottage and it was terrific. It's close to restaurants, a grocery, downtown, and right on the bike path that will take you to the beach. You don't really...
    5 of 5 stars Reviewed 16 June 2014
    We just got back from 5 nights at the largest cottage, Winnipesaukee. We have stayed at other places in Wolfeboro, but this place was the only one I will return. It is very...
    See all reviews
    From
    ₹8,929
    / Night
    Payment Protection
    View Details
    1 / 15
    5 of 5 stars (1) Excellent
    Wolfeboro
    Studio / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    We are renting a lovely apartment situated over a garage. The apartment is open and relaxing with a full kitchen, bathroom with shower (no tub), and a large sleeping area on the top floor with two twin beds and one queen bed. This is a perfect retreat for a couple or family with children. We... View all property information
    Make Enquiry
    Location Information
    Wolfeboro, New Hampshire 03894
    5 of 5 stars Reviewed 13 August 2014
    This property is clean, spacious and very comfortable. Jennifer, the owner, did everything possible to make myself and my 3 children comfortable. My daughter has special needs...
    See all reviews
    From
    ₹36,673
    / Night
    View Details
    1 / 19
    Wolfeboro
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Breathtaking mountain and lake views from your private decks of this wonderfully bright and sunny contemporary. Sit on your dock with 180 view of the lake. Upscale neighborhood, 2 miles from downtown Wolfeboro, includes all the comforts of home plus. WIFI, cable, master bedroom suite, 3.5 baths... View all property information
    Make Enquiry
    Location Information
    Wolfeboro, New Hampshire 03894
    List your property for free!
    List your holiday home where TripAdvisor travellers can find it.
    Add a Listing
    From
    ₹77,492
    / Night
    View Details
    1 / 12
    Wolfeboro
    7 Bedrooms / 3 Bathrooms / Sleeps 14
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    A vacation to remember with this large 6500 sq ft 6-bedroom 4.5 bath waterfront home. House sleeps 14 people, Beautifully appointed with separate guest wing, beach,dock, grill Call for more details Rentals Plus Real Estate: 603-569-6696 rentals@rentals-plus.net View all property information
    Make Enquiry
    Location Information
    Wolfeboro, New Hampshire 03894
    From
    ₹8,228
    / Night
    Payment Protection
    View Details
    1 / 19
    5 of 5 stars (3) Excellent
    Wolfeboro
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    (Please see all 9 of our cottages at CottagesNH.com (our Facebook page). Return to Simplicity. Nine freshly updated Retro 40’s classic Cottages tucked away in the Quaint Lakeside Hamlet of Wolfeboro Falls, the oldest summer resort in America! Your screen door is unlocked and your Cottage keys... View all property information
    Make Enquiry
    Location Information
    Wolfeboro, New Hampshire 03896
    5 of 5 stars Reviewed 3 February 2014
    I fell in love with New Hampshire during our stay at this property. We stayed in Cottage 12, a beautiful cottage and very comfortable. We were very impressed by the comfort of the...
    5 of 5 stars Reviewed 9 July 2013
    My family stayed in two different cottages (6 and 10) over two different weekends . David was extremely helpful accommodating our split schedule since we were dropping off and...
    See all reviews
    From
    ₹76,535
    / Night
    View Details
    1 / 8
    Wolfeboro
    5 Bedrooms / 2 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    For a vacation your family will never forget, this stunning Winnipesaukee lakefront estate carefully incorporates rustic vintage charm with all of the luxurious appointments and details of a 5-Star resort for the most discerning vacationer. This home has been updated with all of the modern... View all property information
    Make Enquiry
    Location Information
    Wolfeboro, New Hampshire 03894
    From
    ₹13,713
    / Night
    Payment Protection
    View Details
    1 / 33
    5 of 5 stars (2) Excellent
    Wolfeboro
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Private Fishing...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Cute, secluded and modernized lakefront cottage with huge deck and private beach overlooking small lake. 1 double bed, 2 twin beds, 1 queen sofabed. Stunning water views from living room, dining area, kitchen and deck. Small private beach and swimming platform plus use of row boat, kayak and peddle... View all property information
    Make Enquiry
    Location Information
    Wolfeboro, New Hampshire 03894
    5 of 5 stars Reviewed 2 April 2015
    I looked through a few places before I made a decision to rent this house. What caught my attention to start was the way the house looks. You never know what you'll find renting...
    5 of 5 stars Reviewed 1 April 2015
    My friends and I ended up staying at this lake house when we visited New Hampshire. We were pleasantly surprised at the quality we received. The lake house was very clean when we...
    See all reviews
    From
    ₹20,983
    / Night
    Payment Protection
    View Details
    1 / 12
    Center Ossipee
    3 Bedrooms / 1 Bathroom / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Private Fishing...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Lakefront home on private beach available for rent by the week on the sunny shores of Leavitt Bay on Ossipee Lake. Prime summer weekly rental rate is $2300. A $100 security deposit is required. Gradual, sandy beach Load your boat from the property, tie up to your own dock and enjoy Ossipee... View all property information
    Make Enquiry
    Location Information
    Center Ossipee, New Hampshire 03814
    From
    ₹12,692
    / Night
    View Details
    1 / 39
    Wolfeboro
    5 Bedrooms / 2 Bathrooms / Sleeps 14
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Return to Simplicity - Drop your keys in the drawer and walk or bike to everything for the rest of this stress free vacation. It is a 3-10 minute walk to most all your vacation needs. Every age is entertained while walking to ice cream parlors, small boutique stores, waterfront shops, shows, &... View all property information
    Make Enquiry
    Location Information
    Wolfeboro, New Hampshire 03894
    From
    ₹20,027
    / Night
    View Details
    1 / 10
    Center Ossipee
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Satellite TV
    • Washer
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Enjoy all that Ossipee Lake has to offer in this in this beautiful and comfortable lakeside home. Spectacular panoramic views of the Ossipee mountains and the lake.Bring your boat or jet ski if you choose. Your private dock awaits! Located on a quiet and private road.A small bunk house will sleep... View all property information
    Make Enquiry
    Location Information
    Center Ossipee, New Hampshire 03814
    From
    ₹14,606
    / Night
    View Details
    1 / 17
    Wolfeboro
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Satellite TV
    • Washer
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Four bedroom/3 bath home with all pine floors. Master loft bedroom with spectacular views of Lake Winnipesaukee. Fieldstone fireplace, white leather furniture in livingroom. All rooms fully furnished. Large wrap-around deck. Washer/dryer on first floor Weekly and monthly rental. Beds: 1... View all property information
    Make Enquiry
    Location Information
    Wolfeboro, New Hampshire 03894
    From
    ₹20,473
    / Night
    View Details
    1 / 21
    Center Ossipee
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Enjoy spectacular views through Walls of Glass in this beautiful lake-front home right on your own sandy beach on Ossipee Lake! This special property, loctated on the western side of the lake (which many consider the most desireable side), has 100 feet of sandy beach frontage. Situated at the end... View all property information
    Make Enquiry
    Location Information
    Center Ossipee, New Hampshire 03814
    From
    ₹10,205
    / Night
    View Details
    1 / 22
    Wolfeboro
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Beautiful cape on Lake Wentworth with southwest views. Enjoy picturesque sunsets from the lakeside deck, dock your boat at the u-shaped dock, and enjoy swimming with a sandy bottom shore. The natural shorefront leads to a level grassy lot with picnic area and outdoor shower. Inside, enjoy the... View all property information
    Make Enquiry
    Location Information
    Wolfeboro, New Hampshire 03894
    Get the List
    From
    ₹159,449
    / Week
    View Details
    1 / 21
    Wolfeboro
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Spacious Winnipesaukee contemporary home conveniently located in South Wolfeboro, minutes to downtown Wolfeboro and a short drive to Alton Bay. Finished on three levels, this light and bright home sits on a nice grassy lot with lots of sun. The main level has one bedroom with queen bed and attached... View all property information
    Make Enquiry
    Location Information
    Wolfeboro, New Hampshire 03894