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Windsor Vacation Rentals

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    Don't let other travelers get your favorite Windsor area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 30 Rentals in Windsor
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    The following rentals are within 15 miles of Windsor.
    Hanover, NH
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Savage Hart Farm - a Sheep Farm with an Apartment1 / 12
    (1)Excellent
    White River Junction
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Beauty & Privacy on 24 acres, sleeps 81 / 10
    (10)Very good
    Brownsville
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Proctorsville
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Satellite TV
    • Washer
    • Patio
    • Hot Tub
    • Mountain Views
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is a beautiful 3 bedroom, 2 bath with large family room and sleeps 10. In winter we are 4 minutes to skiing at the fabulous resort of Okemo/Jackson Gore. You ski, board, ice skate, snowmobile, snow shoe, cross country or go to the spa for a day of fun. At our house we have an outdoor hot...
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    Proctorsville, Vermont 05153
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Charming Cottage Near  Woodstock Vermont1 / 20
    (1)Excellent
    Reading
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Porch
    • Washer
    • Mountain Views
    • Shared Yard
    • Grill
    • Internet Access
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 30, 2014
    We were looking for a quiet spot for our family to get away from our crazy day-to-day life, and we found it! The cabin was great - clean, comfortable, well-stocked - and the...
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    About this property
    Nestled in a private hundred-acre valley crisscrossed with trails, a quiet, beautifully situated antique cabin and fully renovated barn overlooking idyllic Vermont meadow, ponds, hills & creek awaits your discovery. Property abuts the world famous Jenne Farm located twenty minutes south of...
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    Reading, Vermont 05062
    Cabin - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Proctorsville
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Mountain Views
    • Internet Access
    • Washer
    • Satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Surround yourself with rolling hills and meadows at this two-bedroom Vermont escape, a dog-friendly duplex with glorious mountain views, a gorgeous piece of shared property, and nearby access to the slopes of Okemo Mountain Resort. Stunningly situated on an expansive piece of property that...
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    Proctorsville, Vermont 05153
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Brownsville
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Patio
    • Washer
    • DVD Player
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Retreat to your own hideaway in the woods of West Windsor, where views of mountains and valleys greet you through each bright window. Whether you choose to take in the scenery from the deck or warm up by the fireplace, this home is all about slowing down in the mountains. West Windsor Retreat is...
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    Brownsville, Vermont 05089
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Proctorsville
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
    • Internet Access
    • Mountain Views
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the simple pleasures of your very own Vermont farmhouse at this four-bedroom Proctorsville retreat, a duplex with dog-friendly accommodations, sweeping mountain views, and a wonderful location close to Okemo Mountain Resort. This historic farmhouse sits in the middle of an open, grassy...
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    Proctorsville, Vermont 05153
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    Hakuna Matata1 / 28
    (1)Very good
    Bridgewater
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Balcony
    • Mountain Views
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It means no worries, for the rest of your vacation. No service, no problem! That's what makes this home so special, the stress of work and everyday life seem to evaporate the second you arrive. Being surrounded by beautiful scenery, fresh clean air and the sounds of nature have made this a favorite...
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    Bridgewater, Vermont 05035 4409
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Proctorsville
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gaze at gorgeous mountain views in winter, spring, summer, and fall at this two-bedroom Proctorsville retreat, a bright and airy duplex with dog-friendly accommodations, a breathtaking piece of property, and easy driving access to Okemo Mountain Resort. This duplex home is located on the first...
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    Location Information
    Proctorsville, Vermont 05153
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    White River Junction
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Washer
    • Mountain Views
    • Parking
    • Satellite TV
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On the border of Vermont and New Hampshire, Savage Hart Farm is a perfect place to stay for a memorable visit to the heart of New England. You'll find a retreat-type setting close to the center of the towns of Hanover, NH, and Norwich, VT in a bucolic locale even the locals talk about. Quechee is...
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    White River Junction, Hartford 05001
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Grantham, NH
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • Internet Access
    • Parking
    • Central Heating
    • Balcony
    • Washer
    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the Fall colors, Dartmouth football games, Sunapee ski weekends, and all that this beautiful region has to offer. 2BR, 2BA lakefront condo in Eastman, a planned recreational community located in the NH Upper Valley area. This condo was completely renovated in 2015 and features bamboo...
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    Grantham, New Hampshire 03753
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Reading Farms Estate/ Vermont Luxury Rental1 / 53
    (4)Excellent
    Reading
    15 Bedrooms, 12 Bathrooms, Sleeps 44 Quick View
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    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 27, 2015
    We just returned from our stay at Reading Farms and it was truly amazing, the chef cooked us a to die for meal and the staff did a firework show for us our last night that was...
    Reviewed June 26, 2014
    I had a lovely time at Reading Farms Estate over the Memorial Day weekend. The property is stunning, with sweeping views of the surrounding mountains and excellent service and...
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    About this property
    Reading Farms lies in the heart of Vermont. A completely private 400 acre estate. One of Vermont's most majestic properties has been held by the same owners for nearly 100 years. The secluded estate is conveniently located minutes from Woodstock Vermont and two of the best Vermont ski areas...
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    Location Information
    Reading, Vermont 05062
    Rental Home - 15 Bedrooms, 12 Bathrooms, Sleeps 44
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    Brownsville
    Studio, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Porch
    • Internet Access
    • Parking
    • Mountain Views
    • DVD Player
    • Washer
    • Shared Indoor Pool
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The condominium lies on the West face of historical Ascutney Mt in the small town of Brownsville. The condominium consists of 3 bedrooms, 2 1/2 bathrooms, a small family rec room, living room, and dining area. A very comfy and warm atmosphere with access to a full service sports and fitness center....
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    Location Information
    Brownsville, Vermont 05089
    Condo/Apartment - 3 Bathrooms, Sleeps 6
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    South Pomfret
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
    • Wi-Fi
    • Private Yard
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautifully appointed, New England style, separate 2 bedroom/2 bath 2 story main house located in a great area of Central/Southern Vermont. 2 minutes to the village of Woodstock. Biking/Hiking heaven with trails leading from the property- as well as 1 mile to the ski resort. Well maintained,...
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    Location Information
    South Pomfret, Vermont 05067
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Quechee
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Skiing: Property Is In A Ski Resort
    • Central Heating
    • Hot Tub
    • Wi-Fi
    • Shared Indoor Pool
    • Satellite TV
    • Housekeeping Included
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome, this townhouse is located in one of the most beautiful 4 season areas of Vermont. You have many activities close by and great restaurants and shopping as well. If you enjoy golfing, lakes, pools and skiing the Quechee Club is in walking distance. Just a short drive from Dartmouth if you...
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    Location Information
    Quechee, Hartford 05001
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Grantham, NH
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Private Indoor Pool
    • Waterfront
    • Patio
    • Satellite TV
    • Washer
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Forget all your troubles at this 3-bedroom, 2-bathroom tranquil Grantham condo, which comfortably sleeps 6. From the spacious back deck, enjoy lakefront views and lush green pines before beginning a kayaking, biking, fishing or golfing adventure! THE PROPERTY You’ll know you made the right choice...
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    Location Information
    Grantham, New Hampshire 03753
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunapee, NH
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Central Heating
    • Grill
    • Parking
    • Waterfront
    • Washer
    • Internet Access
    • Porch
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You’ll feel like you’re vacationing inside the pages of DWELL magazine in this brand new three/four bedroom lakefront house designed by a prominent Boston architect. Charming Kezar Lake, dotted with old farmhouses and inns, is a well-kept secret in the area. Old-fashioned Vernondale General Store,...
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    Sunapee, New Hampshire 03260
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Secluded, Spectacular House with Mount Ascutney Vi1 / 21
    (4)Very good
    Perkinsville
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • Central Heating
    • Mountain Views
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 29, 2016
    Overall the house is a very good rental option. It is really beautiful inside and outside and has beautiful surroundings. All rooms are really spacious and have comfortable...
    Reviewed September 10, 2015
    Very spacious home and great yard with lots to do..hiking trails close, swimming pool and tennis courts/basketball hoop and pool table inside. Something for everyone. The...
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    About this property
    Beautiful contemporary mountain home in Vermont sitting in 150 acres of private land. Borders a State Park with beautiful trails and an 80 ft Cascade. 5 Bedrooms, sleeps up to 12. This sprawling home features a large kitchen, separate dining room, spacious living room with stone fireplace and...
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    Location Information
    Perkinsville, Vermont 05151
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 bedroom lake home on Crescent lake1 / 12
    (1)Excellent
    Newport, NH
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Waterfront
    • Mountain Views
    • DVD Player
    • Satellite TV
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on a quiet, pristine New Hampshire lake, this home and scenic surroundings provide a haven of rest for your vacation. Our private sandy beach sits on 510 feet of shoreline and invites you to enjoy carefree sunbathing and swimming in a safe, beautiful setting. Shade trees on the grounds...
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    Location Information
    Newport, New Hampshire 03773
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Brownsville
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Yard
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This exceedingly charming cottage on a wooded hilltop just outside of Brownsville has great views of Mt Ascutney and a burbling brook at the base of the hill. The historic converted early 1800's one room school house is filled with many antique furnishings. Hanging in the stairway are photographs...
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    Brownsville, Vermont 05047
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Bridgewater
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Winter, spring, summer and fall, there is always something to do and something to fall in love with at this cozy Vermont vacation home. Kids will love the rustic sturdy bunk beds and folks just love to relax in front of the fire, cozying up to a good book. There are many downhill and cross country...
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    Bridgewater, Vermont 05035
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Bridgewater
    4 Bedrooms, 3 Bathrooms, Sleeps 24 Quick View
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    • Air Conditioning
    • Skiing: Property Is In A Ski Resort
    • DVD Player
    • Hot Tub
    • Satellite TV
    • Wi-Fi
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Simply known as 'The Cabin', this 5,000 S.F. home that is surrounded by ten private acres within brilliant wilderness, the majestic mountain range in your own backyard. Designed with the purpose of bringing people together, it perfect setting for hosting gatherings for friends, families and...
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    Bridgewater, Vermont 05035
    Cabin - 4 Bedrooms, 3 Bathrooms, Sleeps 24
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    Bridgewater
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Internet Access
    • Washer
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It means no worries, for the rest of your vacation. No service, no problem! That's what makes this home so special, the stress of work and everyday life seem to evaporate the second you arrive. Being surrounded by beautiful scenery, fresh clean air and the sounds of nature have made this a favorite...
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    Location Information
    Bridgewater, Vermont 05035
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Perkinsville
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Mountain Views
    • Grill
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Housekeeping Included
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and enjoy a beach view in VT! refreshing yourself in a lovely beach painting room. Our place is a 200 year old farmhouse which is located in a big farm scenic private area in Perkinsville, Vermont. We have a covered bridge at one end of our road. It's quiet dirt road which is perfect for...
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    Perkinsville, Vermont 05151
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Perkinsville
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Air Conditioning
    • DVD Player
    • Washer
    • Mountain Views
    • Housekeeping Included
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A cozy and comfortable room with the sun shines all day! It is an opened bright space with big windows all around. Our place is a 200 year old farmhouse which is located in a big farm scenic private area in Perkinsville, Vermont. We have a covered bridge at one end of our road. It's quiet dirt road...
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    Perkinsville, Vermont 05151
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sunapee, NH
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Terrace
    • DVD Player
    • Balcony
    • Grill
    • Central Heating
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy, family townhouse on a wooded lot overlooking private golf course (free unlimited golf included, clubs available). Fully equipped kitchen and laundry, linens provided 2 minute walk from private, sandy beach and boathouse, includes unlimited usage of community kayaks and canoes free of charge...
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    Sunapee, New Hampshire 03782
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cavendish
    6 Bedrooms, 10 Bathrooms, Sleeps 17 Quick View
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    • Satellite TV
    • Patio
    • Hot Tub
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The property includes 7 bedrooms (robes, bath amenities, tempurpedic beds, fireplaces, vable television, DVD and ensuite baths in all but 2), 8-person hot tub, dining for 24. Great for large groups or big families or specialb events. Warm weather Rustic Barn with bar can seat up to 115 guest...
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    Cavendish, Vermont 05142
    Rental Home - 6 Bedrooms, 10 Bathrooms, Sleeps 17
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    Perkinsville
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Air Conditioning
    • Grill
    • Mountain Views
    • Housekeeping Included
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautiful bed and breakfast Vermont getaway! with 3 comfortable bedrooms available. Our place is a 200 year old farmhouse which is located in a big farm scenic private area in Perkinsville, Vermont. We have a covered bridge at one end of our road. It's quiet dirt road which is perfect for biking,...
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    Location Information
    Perkinsville, Vermont 05151
    Private Room - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Perkinsville
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Housekeeping Included
    • Washer
    • Grill
    • Mountain Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You will definitely love this classic, unique, beautiful and comfortable studio room. It's a great space for your vocation. Our place is a 200 year old farmhouse which is located in a big farm scenic private area in Perkinsville, Vermont. We have a covered bridge at one end of our road. It's quiet...
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    Location Information
    Perkinsville, Vermont 05151
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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