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Ossipee Cottages

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    Don't let other travelers get your favorite Ossipee area vacation rental. You're so close to securing your perfect getaway. Book today.
    22 Matching Rentals in the Ossipee AreaView all 50 rentals
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    Ossipee
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    The following rentals are within 10 miles 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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    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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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Mountain Views
    • Waterfront
    • Washer
    • Balcony
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    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 July 17, 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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    Location Information
    Wolfeboro, New Hampshire 03894
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 7
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    Ossipee Retreat1 / 14
    (19)Very good
    Freedom
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travelers have booked this property
    This was my first Flip Key rental and we absolutely were thrilled to have such a nice cottage and a patient owner who helped us understand the experience.
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    Amenities & Details
    • Grill
    • Parking
    • DVD Player
    • Central Heating
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 23, 2018
    Ossipee Retreat was the perfect, quiet get-away for our family of 4. We had access to the area's private beach and rented kayaks at the Ossippee Lake Marina (both within...
    Reviewed July 12, 2018
    Very nice. everything it advertised. Ideal location 1/2 hr to the white Mtns, 45 min to the maine coast. convenient to services. Beach club was amazing, very friendly people...
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    About this property
    Rustic relaxation with all the modern conveniences!! In less than 2.5 hours drive from Boston you can be enjoying the sun on the beach or the ski slopes in the Lakes Region of New Hampshire while staying in this all season vacation home located near Lake Ossipee in the town of Freedom, New...
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    Location Information
    Freedom, New Hampshire 03836
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    Amenities & Details
    • Wi-Fi
    • Washer
    • Grill
    • Mountain Views
    • Porch
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 3, 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 July 8, 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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    Location Information
    Wolfeboro, New Hampshire 03894
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Wolfeboro Lakehouse Retreat1 / 32
    (5)Excellent
    Wolfeboro
    2 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
    other travelers have booked this property
    The cottage is perfect: everything you need with a beautiful view of the lake and comfortable beds.
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    Amenities & Details
    • Patio
    • Hot Tub
    • DVD Player
    • Balcony
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 1, 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 September 5, 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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    Location Information
    Wolfeboro, New Hampshire 03894
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 10
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    Wolfeboro
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Secure Parking
    • Air Conditioning
    • Private Yard
    • Wi-Fi
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sweet Apple Camp is very private, with french doors overlooking the old apple orchard, the Ruins, and the woodland beyond, It features a queen bed, full bathroom, and small kitchen with a pine peninsula and barstools. It also has an entry deck, outdoor seating, a hammock, and a charcoal grill. This...
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    Location Information
    Wolfeboro, New Hampshire 03894
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Wolfeboro
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Mountain Views
    • Wi-Fi
    • Grill
    • Secure Parking
    • Waterfront
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Black Bear Camp, formerly listed as Ehawee Camp, will have a beautiful bedroom addition for 2018! It will feature this master bedroom with a queen bed, nightstands, and closets. The living room has a queen memory foam sofa bed, a full bathroom, and a small kitchen with a pine peninsula and...
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    Location Information
    Wolfeboro, New Hampshire 03894
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Wolfeboro
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Patio
    • Grill
    • Secure Parking
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Copple Crown Camp features a hickory queen bed, hickory nightstands, a full bathroom, and a small kitchen with a pine peninsula and barstools. It has outdoor seating and a charcoal grill, and looks out onto the Great Lawn and orchard. Copple Crown Mountain can be seen at the end of Rust Pond, and...
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    Location Information
    Wolfeboro, New Hampshire 03894
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    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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    Amenities & Details
    • Washer
    • Mountain Views
    • Waterfront
    • Parking
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 16, 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 July 7, 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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    Location Information
    Wolfeboro, New Hampshire 03894
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 9
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    Fun Family Wolfeboro Village Waterfront Cottage1 / 17
    (1)Excellent
    Wolfeboro
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Mountain Views
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming Wolfeboro waterfront cottage in the heart of antique boat land - as seen in the Guardian. In the summer watch the gorgeous wooden boats cruise by or the Wolfeboro water ski team jump and slalom in the bay. Wolfeboro center is 5 minutes walk or 2 minutes food shopping by boat. Enjoy an...
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    Location Information
    Wolfeboro, New Hampshire 03894
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Wolfeboro
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • 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...
    View all property information
    Location Information
    Wolfeboro, New Hampshire 03894
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Wolfeboro
    1 Bedroom, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • 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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 7
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    Wolfeboro
    1 Bedroom, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • 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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 7
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    Clark's Landing Cottages (VER05W)1 / 25
    (1)Excellent
    Melvin Village
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 27, 2017
    Beautiful location for a family vacation, the cabins are comfortable accommodation and there are lots of activities in the area to explore. LOVE staying at Clarks Landing at...
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    About this property
    Cozy, comfortable and quaint! Come enjoy a stay at this adorable 2 bedroom cottage located on Lake Winnipesaukee in Moultonborough, NH. This is a small cottage community known as Clark’s Landing and each cottage is lovingly and meticulously created and cared for. Nostalgia at it's best -...
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    Location Information
    Melvin Village, New Hampshire 03254
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 8
    Make Inquiry
    Melvin Village
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Show Prices
    Amenities & Details
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy, comfortable and quaint! Come enjoy a stay at this adorable 2 bedroom cottage located on Lake Winnipesaukee in Moultonborough, NH. This is a small cottage community known as Clark’s Landing and each cottage is lovingly and meticulously created and cared for. Nostalgia at it's best -...
    View all property information
    Location Information
    Melvin Village, New Hampshire 03254
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    Melvin Village
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy, comfortable and quaint! Come enjoy a stay at this adorable 2 bedroom cottage located on Lake Winnipesaukee in Moultonborough, NH. This is a small cottage community known as Clark’s Landing and each cottage is lovingly and meticulously created and cared for. Nostalgia at it's best -...
    View all property information
    Location Information
    Melvin Village, New Hampshire 03254
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Inquiry
    Wolfeboro
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • 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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Wolfeboro
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • 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...
    View all property information
    Location Information
    Wolfeboro, New Hampshire 03894
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 5
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    East Wakefield
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Location Information
    East Wakefield, Wakefield 03830
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Ossipee Flight and Weather Info
    Airports nearby (1)
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    PWM
    Portland Intl Jetport
    40.4 miles from Ossipee
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