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Holiday Rentals and Homes in Wolfeboro, NH

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    Travellers to Wolfeboro are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 32
    5 of 5 stars (3) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 90
    5 of 5 stars (6) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    1 / 15
    5 of 5 stars (2) Excellent
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    5 Bedrooms, 2 Bathrooms, Sleeps 14 | Quick View
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    • Washer
    • Outdoor Dining Area
    • Patio
    • Balcony
    • Wi-Fi
    • Terrace
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Gorgeous Victorian Main House (newly renovated) that can sleep up to 14 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... View all property information
    Location Information
    Wolfeboro, New Hampshire 03896
    1 / 70
    5 of 5 stars (15) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Washer
    • Mountain Views
    • Waterfront
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    • Satellite TV
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    • Child-friendly
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    • ?
    About this property
    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 will be on the counter waiting for you… so put your car keys away and wander... View all property information
    Location Information
    Wolfeboro, New Hampshire 03894
    5 of 5 stars Reviewed 3 weeks ago
    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...
    5 of 5 stars Reviewed 3 weeks ago
    Our family stayed in the Caretaker's House for a family wedding. So wonderful to be together in one location along with relatives and friends in the cottage compound. Staff was...
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    1 / 76
    5 of 5 stars (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Wi-Fi
    • Porch
    • Parking
    • Washer
    • Outdoor Dining Area
    • Waterfront
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    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 will be on the counter waiting for you… so put your car keys away and wander... View all property information
    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 8 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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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Mountain Views
    • Patio
    • Grill
    • Secure Parking
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wolfeboro, New Hampshire 03894
    1 / 17
    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
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wolfeboro, New Hampshire 03894
    1 / 58
    5 of 5 stars (3) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 15 | Quick View
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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.... View all property information
    Location Information
    Wolfeboro, New Hampshire 03894
    5 of 5 stars Reviewed 3 weeks ago
    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 all...
    5 of 5 stars 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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    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
    • Secure Parking
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Quaint one room efficiency condo, w/ mini fridge, microwave, toaster, coffee maker, and downtown parking. Second floor unit located on Main Street, downtown Wolfeboro NH. Comfortable and clean, one bedroom condominium, located downtown Wolfeboro, Americas Oldest Summer Resort. This condo is... View all property information
    Location Information
    Wolfeboro, New Hampshire 03894
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
    • DVD Player
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunny, one bedroom, condo w/ washer & dryer, full kitchen, and downtown parking Charming, one bedroom condominium, located downtown Wolfeboro, the oldest summer resort in America. This condo is perfect for a romantic get away, wedding weekend or family vacation. The condo consists of a bedroom,... View all property information
    Location Information
    Wolfeboro, New Hampshire 03894
    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
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wolfeboro, New Hampshire 03894
    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
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wolfeboro, New Hampshire 03894
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    Amenities & Details
    • Patio
    • Secure Parking
    • Grill
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wolfeboro, New Hampshire 03894
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    Amenities & Details
    • Satellite TV
    • Grill
    • Patio
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Wolfeboro, New Hampshire 03894
    1 / 8
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Washer
    • Waterfront
    • Internet Access
    • Patio
    • DVD Player
    • Grill
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Wolfeboro, New Hampshire 03894
    1 / 50
    5 Bedrooms, 2 Bathrooms, Sleeps 14 | Quick View
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    • Air Conditioning
    • Balcony
    • Washer
    • Porch
    • DVD Player
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    See more at our site CottagesNH and our 9 Cottages (can host up to 54) 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... View all property information
    Location Information
    Wolfeboro, New Hampshire 03894
    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Grill
    • DVD Player
    • Porch
    • Parking
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    2 bedrooms (1Q, 1DB ), 1 bath, with 1 queen sleeper sofa & 1 double sleeper sofa, living room, kitchen;Linens available. Log Cabin sets on 28.8 acres, with seasonal farm animals (goats, chickens, guineas;fresh eggs when available) area to play and have fun. Minutes to King Pine Ski Area in Madison... View all property information
    Location Information
    Wolfeboro, New Hampshire
    1 / 17
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Parking
    • Washer
    • Satellite TV
    • DVD Player
    • Waterfront
    • Grill
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    Location Information
    Wolfeboro, New Hampshire 03894