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Holiday Rentals in Wolfeboro

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    Travellers to Wolfeboro are booking October dates now. Secure your holiday rental today, and have the perfect trip.
    All 26 Rentals in Wolfeboro
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    Mt Washington Cabin #11 of 12, for 2-7 Guest, Wolfeboro, near Lake Winnipesaukee1 / 99
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 7 Quick View
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    Lake Wnni Cabin#9 of 12, for 2-9 Guests, Wolfeboro, near Lake Winnipesaukee1 / 66
    (16)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Squam Lake Cabin#7 of 12, for 2-4 Guests, Wolfeboro, near Lake Winnipesaukee1 / 84
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Satellite TV
    • Grill
    • Patio
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Grey Shingles Camps property has been a cottage colony since the 1940's. We have just completed extensive renovations! Our aim is to have our guests experience the vacations of old with a modern sensibility. Rust Pond Camp is the largest of our five camps. We are able to rent the entire...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Brick House Wolfeboro - Dogs Welcome1 / 57
    (3)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • 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
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    Wolfeboro Lakehouse Retreat1 / 32
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • Patio
    • Parking
    • Balcony
    • Waterfront
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 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...
    Reviewed 6 August 2015
    My 2 dgts and 2 grandchildren stayed for 1 week we loved the town of Wolfeboro..the house was peaceful the pond clean the waterfront was very enjoyable.....we traveled to...
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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. 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...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Spacious 4 Bedroom Family Home, close to town1 / 9
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Central Heating
    • Patio
    • Grill
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Our daughter got married at the Wolfeboro Inn - less than a mile away. The home is in a quiet, friendly neighborhood where the main road runs along the side of the Wolfeboro...
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    About this property
    Comfortable, private family home, walking distance to downtown. Bordered by conservation land with walking trails right off the driveway. Located on private cul-de-sac with no through traffic. Sleeps 9 in 4 bedrooms. Close to all of the amenities of town and Lake Winnipesaukee. Close to town...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Mountain Views
    • Wi-Fi
    • Grill
    • Secure Parking
    • Waterfront
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Grey Shingles Camps property has been a cottage colony since the 1940's. We have just completed extensive renovations! Our aim is to have our guests experience the vacations of old with a modern sensibility! Ehawee Camp overlooks the Great Lawn and has a summer camp theme. The property...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    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 Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Grey Shingles Camps property has been a cottage colony since the 1940's. We have just completed extensive renovations! Our aim is to have our guests experience the vacations of old with a modern sensibility! Copple Crown Camp has a view of the great lawn and celebrates our NH mountains with...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Fun Family Wolfeboro Village Waterfront Cottage1 / 17
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Internet Access
    • Patio
    • DVD Player
    • Central Heating
    • Satellite TV
    • Hot Tub
    • 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Private Retreat in Woods on Pristine Rust Pond1 / 19
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • DVD Player
    • Grill
    • Balcony
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 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...
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    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...
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    Wolfeboro, New Hampshire 03894
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Victorian Home, 14-18P, In Town Wolfeboro, Lakes Region, near Lake Winnipesaukee1 / 34
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
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    • Washer
    • Outdoor Dining Area
    • Patio
    • Balcony
    • Wi-Fi
    • Terrace
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 March 2017
    The place was large, clean and felt like home, David was informative and helpful and was always available for questions or concerns. I am however disappointed in tripadvisor...
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    About this property
    Gorgeous Victorian Main House (newly renovated) that can sleep up to 17 people (open year round) as well as 9 Charming Updated Seasonal Cabin Rentals tucked into the only private woodlands in this “Norman Rockwellesque” Quaint Downtown! Put your keys in a drawer for the week and stroll, bike or...
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    Wolfeboro, New Hampshire 03896
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 18
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    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
    • Terrace
    • Balcony
    • 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 currently being renovated, and will feature a large eat-in kitchen, twin bunk beds, a living room with a cathedral ceiling and queen sofa bed, and a spacious master bedroom with a...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • Patio
    • Waterfront
    • Secure Parking
    • Air Conditioning
    • Grill
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Grey Shingles Camps property has been a cottage colony since the 1940's. We have just competed extensive renovations! Our aim is to have our guests experience the vacations of old with a modern sensibility. Sweet Apple Camp overlooks the Great Lawn, the Ruins, and the old Apple Orchard. The...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Satellite TV
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring the dogs to the lakes! Walk to downtown Wolfeboro and the beach. Hop on your bike and coast from the front door to the Bridge Falls Path and pedal as far as you want to go. Bring the kayaks, canoes and stand up paddleboards. Just down the street is the Mast Landing public boat launch on...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Spruce Camp at Grey Shingles Camps1 / 32
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Secure Parking
    • Grill
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 August 2017
    This is a very special place. The cabins are newly renovated and therefore clean and very efficient. Perfect for a family or individual looking for a place that offers plenty of...
    Reviewed 9 August 2016
    Grey Shingles camps is a wonderful place to spend some quality family time. Our cabin was clean, comfortable, and well-appointed. Robin and Rich are gracious and...
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    About this property
    The Grey Shingles Camps property has been a cottage colony since the 1940's. We have just completed extensive renovations in our 5 camps and Recreation Hall! Our aim is to have our guests experience the vacations of old with a modern sensibility. In addition to renting camps individually, we are...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Air Conditioning
    • Parking
    • Grill
    • Wi-Fi
    • Waterfront
    • 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
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • DVD Player
    • Air Conditioning
    • Parking
    • Sauna
    • Washer
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rating: 3-star Location:Situated in the town of Wolfeboro, America's Oldest Summer Resort', this resort is nestled in the mountains of the New Hampshire Lakes Region. It is a 15-minute walk to downtown Wolfeboro and Lake Winnipesaukee. Area Attractions:Within 2 miles (4km) of the resort are...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 7 Quick View
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    • Parking
    • Wi-Fi
    • Air Conditioning
    • Grill
    • 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...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 7
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    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Sauna
    • DVD Player
    • Parking
    • Air Conditioning
    • Balcony
    • Washer
    • Internet Access
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rating: 3-star Location: Situated in the town of Wolfeboro, America's Oldest Summer Resort', this resort is nestled in the mountains of the New Hampshire Lakes Region. It is a 15-minute walk to downtown Wolfeboro and Lake Winnipesaukee. Area Attractions: Within 2 miles (4km) of the resort...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A charming 1770 historic farm house! Enjoy "The Ridge" a private 3 bed 2 bath accommodations including linens, towels and a full kitchen with pots/pans and utensils. Plenty of room, home away from home. Enjoy hiking, skiing, swimming, boating, historic sites, museums and much more. The beautiful...
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    Wolfeboro, New Hampshire 03864
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    1 Bedroom, 1 Bathroom, Sleeps 7 Quick View
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    • Mountain Views
    • Air Conditioning
    • Washer
    • Parking
    • 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
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 7
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    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Balcony
    • Sauna
    • Parking
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rating: 3-star Location:Situated in the town of Wolfeboro, 'America's Oldest Summer Resort', this resort is nestled in the mountains of the New Hampshire Lakes Region. It is a 15-minute walk to downtown Wolfeboro and Lake Winnipesaukee. Area Attractions:Within 2 miles (4km) of the resort are...
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Waterfront
    • 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
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Waterfront
    • Parking
    • Grill
    • Mountain Views
    • 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
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    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • 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
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    Wolfeboro, New Hampshire 03894
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
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