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Pet Friendly Holiday Rentals in Ossipee

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    27 Matching Rentals in the Ossipee AreaView all 61 rentals
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    The following rentals are within 15 kilometres of Ossipee.
    Rust Pond Camp at Grey Shingles Camps1 / 34
    (1)Excellent
    Wolfeboro
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Spruce Camp at Grey Shingles Camps1 / 32
    (3)Excellent
    Wolfeboro
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    Quaint Cottage in Private Wooded Setting | Close to Lakes | Dogs Welcome1 / 34
    (1)Excellent
    Wolfeboro
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Squam Lake Cabin#7 of 12, for 2-4 Guests, Wolfeboro, near Lake Winnipesaukee1 / 84
    (3)Excellent
    Wolfeboro
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Washer
    • Grill
    • Mountain Views
    • Porch
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
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    About this property
    This is just One of Ten Opportunities at The Cottages of Wolfeboro which you can see by Searching for our Name in your Browser. 3 for couples, 3 for 4-6 people & 3 for 4-9 & a House for 14-18. Return to Simplicity. No Shoes, no keys, no technology required... Choose from our Nine freshly updated...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Mt Washington Cabin #11 of 12, for 2-7 Guest, Wolfeboro, near Lake Winnipesaukee1 / 99
    (7)Very good
    Wolfeboro
    1 Bedroom, 1 Bathroom, Sleeps 7 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Mountain Views
    • Waterfront
    • Washer
    • Balcony
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 September 2018
    Really disappointed in this cabin. Very cramped for two adults-can't imagine adding two children in the mix. No where to relax except on the beds which were nice. The beach...
    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...
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    About this property
    This is just One of Ten Opportunities at The Cottages of Wolfeboro which you can see by Searching for our Name in your Browser. 3 for couples, 3 for 4-6 people & 3 for 4-9 & a House for 14-18. Return to Simplicity. No Shoes, no keys, no technology required... Choose from our Nine freshly updated...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 7
    Lake Wnni Cabin#9 of 12, for 2-9 Guests, Wolfeboro, near Lake Winnipesaukee1 / 66
    (16)Excellent
    Wolfeboro
    2 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Mountain Views
    • Waterfront
    • Parking
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 2016
    Cleanest cottages we've ever rented. Well-appointed and cute decor. Plenty to do in the area. Something for everyone - we were an extended family ranging in age from 10 - 85. We...
    Reviewed 7 July 2016
    We came here with a bunch of friends for 4th of July weekend, and it could not have been more perfect! Dave and the rest of the staff were so gracious and helpful. The house was...
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    About this property
    This is just One of Ten Opportunities at The Cottages of Wolfeboro which you can see by Searching for our Name in your Browser. 3 for couples, 3 for 4-6 people & 3 for 4-9 & a House for 14-18. Return to Simplicity. No Shoes, no keys, no technology required... Choose from our Nine freshly updated...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 9
    Wolfeboro
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Grill
    • Waterfront
    • Mountain Views
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is just One of Ten Opportunities at The Cottages of Wolfeboro which you can see by Searching for our Name in your Browser. 3 for couples, 3 for 4-6 people & 3 for 4-9 & a House for 14-18. Return to Simplicity. No Shoes, no keys, no technology required... Choose from our Nine freshly updated...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
    Wolfeboro
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
    • Terrace
    • Balcony
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Nellie's View, an 850 SF lakefront cottage on pristine Rust Pond, in Wolfeboro, New Hampshire! The home is has just been renovated, and features a large eat-in kitchen, kid-sized birch bunk beds, a living room with a cathedral ceiling and queen memory foam sofa bed, and a spacious master...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
    Wolfeboro Lakehouse Retreat1 / 32
    (5)Excellent
    Wolfeboro
    2 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    • Patio
    • Hot Tub
    • DVD Player
    • Balcony
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2018
    The cottage is perfect: everything you need with a beautiful view of the lake and comfortable beds. Sargent's Pond is a small, crystal clear lake, with warmer water than the...
    Reviewed 6 September 2016
    We wanted a place where we could relax, this was definitely it. We relaxed on the porch with a beautiful, peaceful view. The beachfront was perfect for our 5 year old and we...
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    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 in main house. Optional bunkhouse sleeps up to 4 more. Stunning water views from living room, dining area, kitchen and deck. Small private beach and...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 10
    Melvin Village
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your peaceful Lake Winnipesaukee awaits in this spacious water-front hideaway - Property 402. Sleeping eight, this three-bedroom home overlooks the beautiful Lake Winnipesaukee with southern exposure and offers all the comforts of home. Guests can get a good night’s sleep in the king-sized...
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    Melvin Village, New Hampshire 03850
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Wolfeboro
    1 Bedroom, 1 Bathroom, Sleeps 7 Quick View
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    • Mountain Views
    • Air Conditioning
    • Washer
    • Parking
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is just One of Ten Opportunities at The Cottages of Wolfeboro which you can see by Searching for our Name in your Browser. 3 for couples, 3 for 4-6 people & 3 for 4-9 & a House for 14-18. Return to Simplicity. No Shoes, no keys, no technology required... Choose from our Nine freshly updated...
    View all property information
    Location Information
    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 7
    Wolfeboro
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Waterfront
    • Cable/satellite TV
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is just One of Ten Opportunities at The Cottages of Wolfeboro which you can see by Searching for our Name in your Browser. 3 for couples, 3 for 4-6 people & 3 for 4-9 & a House for 14-18. Return to Simplicity. No Shoes, no keys, no technology required... Choose from our Nine freshly updated...
    View all property information
    Location Information
    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
    Wolfeboro
    1 Bedroom, 1 Bathroom, Sleeps 7 Quick View
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    • Parking
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is just One of Ten Opportunities at The Cottages of Wolfeboro which you can see by Searching for our Name in your Browser. 3 for couples, 3 for 4-6 people & 3 for 4-9 & a House for 14-18. Return to Simplicity. No Shoes, no keys, no technology required... Choose from our Nine freshly updated...
    View all property information
    Location Information
    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 7
    Wolfeboro
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Waterfront
    • Parking
    • Grill
    • Mountain Views
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is just One of Ten Opportunities at The Cottages of Wolfeboro which you can see by Searching for our Name in your Browser. 3 for couples, 3 for 4-6 people & 3 for 4-9 & a House for 14-18. Return to Simplicity. No Shoes, no keys, no technology required... Choose from our Nine freshly updated...
    View all property information
    Location Information
    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Three Level In-Town Home | Perfect for Large Families or Groups | Dogs Welcome1 / 52
    (3)Excellent
    Wolfeboro
    6 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 July 2016
    I loved the history of the home and was amazed at how spacious it was. It is very old yet had both antique and modern furnishings. Six of us piled in for the weekend and we...
    Reviewed 7 June 2016
    Stayed the weekend - beds are so comfy you don't want to get out! The house is so beautifully done, but doesn't make you feel like you can't enjoy it. Space galore, the screened...
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    About this property
    In Wolfeboro for a wedding, a special event, or just to relax and enjoy all that the Lakes Region has to offer, the Brick House is a spacious home with privacy and room for large families or groups. With six bedrooms, three and a half baths, two screened porches, an open porch, outdoor dining, etc....
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 15
    Sunset Lodges on Lake Winnipesaukee - Lodge #71 / 5
    (1)Very good
    Mirror Lake
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Grill
    • Wi-Fi
    • Waterfront
    • Central Heating
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunset Lodges is a 1950s era lakeside resort. Located on Lake Winnipesaukee's coveted 'The Basin,' Lodge #7 is the largest lodge, with a master BR on the 1st floor, and 2 BRs on the 2nd floor. Full kitchen with everything you need. First full bathroom with tub/shower, and second full bathroom with...
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    Mirror Lake, New Hampshire 03853
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    Center Ossipee
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Waterfront
    • Air Conditioning
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pauli Point You will not want to leave this amazing waterfront home - just bring your boat (mooring provided) and some sunblock. Swim, play, and boat right from your back door! Relax in the screened porch overlooking the water, or grill on the deck with stunning mountain views. This is a...
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    Center Ossipee, New Hampshire 03836
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Center Ossipee
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Waterfront
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Long Sands Lakefront Home Book this charming, one-dog-friendly house in the White Mountain State and leave all of your worries behind! Featuring an incredibly inviting living room area with comfortable leather couches, a furnished balcony overlooking the Ossipee lake, a beautiful enclosed dining...
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    Center Ossipee, New Hampshire 03814
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Melvin Village
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lakeside Family Retreat Create family memories that you will treasure at this home located on Lake Winnipesaukee. Whether you are swimming at the community beach, playing in the park area, or just enjoying a quiet morning sitting on the screened-in-porch admiring the views, there will never be a...
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    Melvin Village, New Hampshire 03254
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Tuftonboro
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hidden Valley Cottage Hidden Valley Cottage is the family and dog-friendly getaway you’ve been looking for to truly relax and leave all of your problems behind! Boasting a charming vibe, this vacation rental is meant to be your home away from home. It offers an open layout concept with a...
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    Tuftonboro, New Hampshire 03894
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Freedom
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Balcony
    • Air Conditioning
    • Terrace
    • Parking
    • Patio
    • Grill
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lakefront contemporary house with stunning view and sunsets. Steps from the lake and a short drive to many of NH finest attractions. Cosy warm house in colder months in a wonderful part of America. Sun trap deck to catch the sun and enjoy the atmosphere. There is a large West facing wrap around...
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    Freedom, New Hampshire 03836
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
    Tuftonboro
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Tentrr Lava Rock campsite is in Canaan Valley in Tuftonboro, NH, located in the Ossipee Mountains. The mountains are what is left of an old extinct volcano that erupted around 100 million years ago. After three eruptions ten million years apart, the famous ring dike was formed. There are only...
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    Tuftonboro, New Hampshire 03816
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    East Wakefield
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Washer
    • Grill
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Freedom is what everyone desires on vacation, and this outstanding water-front East Wakefield vacation rental cottage will give you exactly that. Settled on 100 feet of pristine Pine River Pond shoreline in a secluded cove, this newly renovated house has everything you need for the ultimate...
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    East Wakefield, Wakefield 03830
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
    Wolfeboro
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Air Conditioning
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    • Grill
    • Wi-Fi
    • Waterfront
    • Cable/satellite TV
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is just One of Ten Opportunities at The Cottages of Wolfeboro which you can see by Searching for our Name in your Browser. 3 for couples, 3 for 4-6 people & 3 for 4-9 & a House for 14-18. Return to Simplicity. No Shoes, no keys, no technology required... Choose from our Nine freshly updated...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
    Freedom
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Cable/satellite TV
    • Hot Tub
    • Central Heating
    • DVD Player
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fife and Drum Beach Home Make this spacious and dog-friendly house in New Hampshire your next home base to create everlasting memories with your group of friends or family! The cabin-like interior and the comfortable furnishing will give you those relaxing vibes you’ve been looking for. Gather...
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    Freedom, New Hampshire 03836
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    Freedom
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Grill
    • Terrace
    • Waterfront
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    • Washer
    • Balcony
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This family friendly lakefront home is located on beautiful Broad Bay of Ossipee Lake, in the White Mountains of New Hampshire. It is an ideal location to enjoy all sections of the lake. It’s a quick ride to the sand bar, where you can play a game of volleyball in the water, or to the big lake...
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    Freedom, New Hampshire 03836
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Center Ossipee
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
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    • Mountain Views
    • Cable/satellite TV
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take a break from the daily routine at this 3-bedroom, 1-bath cottage on Lake Ossipee! Your new routine will include swimming in the calm waters of the lake, soaking up the sun on the private sand beach, and barbecuing on the sunny deck! Bring your own boat or jet ski to dock it at this vacation...
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    Location Information
    Center Ossipee, New Hampshire 03814
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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