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Windsor Holiday Homes

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    Don't let other travellers get your favourite Windsor area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 34 Rentals in Windsor
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    The following rentals are within 25 kilometres of Windsor.
    Hakuna Matata1 / 28
    (1)Very good
    Bridgewater
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The Farmhouse1 / 18
    (1)Excellent
    South Pomfret
    2 Bedrooms, 2 Bathrooms, Sleeps 4 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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    Proctorsville
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Bridgewater
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Mountain Views
    • Internet Access
    • Patio
    • 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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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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
    • Cable/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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    Proctorsville
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Washer
    • Central Heating
    • Mountain Views
    • DVD Player
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedrooms, 1 Bathroom, Sleeps 6 has Sofa Bed for kids. This home is located 5 miles from Okemo Mountain. Okemo is a great family resort for skiing. If its snowmobile trails you are looking for the house is near VAST Trails. Also there is snowmobile rental about 1 mile away. There is a shuttle...
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    Proctorsville, Vermont 05153
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Bridgewater
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • Parking
    • Mountain Views
    • Washer
    • Grill
    • DVD Player
    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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 bedroom lake home on Crescent lake1 / 11
    (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
    • Cable/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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    Newport, New Hampshire 03773
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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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
    • Cable/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
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Secluded, Spectacular House with Mount Ascutney Vi1 / 20
    (4)Very good
    Perkinsville
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Internet Access
    • Central Heating
    • Mountain Views
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 March 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 11 September 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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Perkinsville
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Perkinsville, Vermont 05151
    Private Room - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Brownsville
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • DVD Player
    • Central Heating
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautiful, antique farmhouse with 26 acres, situated on a quiet country road,but only a short drive to stores, great restaurants, and outdoor activities. The farmhouse is located in Brownsville and is a short drive to Woodstock, Quechee, skiing and the Green Mountain Horse Association show...
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    Brownsville, Vermont 05089
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Brownsville
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • 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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    • Central Heating
    • DVD Player
    • Patio
    • Parking
    • Balcony
    • Mountain Views
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Wonderful House in Brownsville, Vermont 1/4 mi to Ascutney Mountain Resort (hiking, biking, but skiing is closed) 12 miles to Woodstock, VT 30 minutes to Mount Okemo. 4 hours to Manhattan via Merrit Pkwy and I-91 3 hours to Boston The perfect vacation spot for leaf-peeping, or just kicking...
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    Brownsville, Vermont 05037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Newport, NH
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Housekeeping Included
    • Porch
    • DVD Player
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Skiing: Property Is In A Ski Resort
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    90 minutes from Boston & just 5 miles from the summer fun of Lake Sunapee & Mount Sunapee, the 'Lodge' is a truly unique space with timeless and upscale accommodations that make this far more than your traditional rental destination! Located at the historic estate and summer residence of 2-term New...
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    Newport, New Hampshire 03773
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Mountain Views
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 July 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 27 June 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
    Holiday Rental House - 15 Bedrooms, 12 Bathrooms, Sleeps 44
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    Cavendish
    6 Bedrooms, 10 Bathrooms, Sleeps 17 Quick View
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    • Cable/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
    Holiday Rental House - 6 Bedrooms, 10 Bathrooms, Sleeps 17
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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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    Reading
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Private Garden
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ski dates still available! Convenient, updated village farmhouse, 2 hrs from Boston, mins to GMHA, Okemo, Killington, Ascutney, Suicide Six, XC skiing. WiFi, high-speed internet, Netflix, Pandora, smartTV. Fine dining, pubs, art galleries, Long Trail & Harpoon, cheese-making, apple-picking & maple...
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    Location Information
    Reading, Vermont 05062
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    Cavendish
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is less then 10 minutes to the base of Okemo Mountain yet it's in a secluded quiet development. This spacious home has 4 bedrooms and 2 1/2 baths. There is plenty of seating in the kitchen and dining room. There are TV's int he family room as well as the master bedroom and one queen...
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    Cavendish, Vermont 05142
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Proctorsville
    5 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    • Patio
    • DVD Player
    • Wi-Fi
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Cable/satellite TV
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that the homeowner lives on site, in a separate house out of sight ** Sitting on a plateau above the Williams River you'll find the 'Smokeshire Hilltop Farmhouse,' a 5-bedroom, 2-bathroom vacation rental home in Chester. This 3,000-square-foot classic farmhouse for up to 14 sits...
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    Proctorsville, Vermont 05143
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 14
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    Proctorsville
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    • DVD Player
    • Washer
    • Wi-Fi
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedrooms, 2 full Bathrooms, Sleeps 6 adults with 2 sofa sleepers for children This house is 5 miles from Okemo skiing. Nearby are VAST snowmobile trails. There shuttle service from house to Okemo Mountain so you don't have to deal with parking. Killington Mt is 18 miles. Nearby snowmobile...
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    Proctorsville, Vermont 05153
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    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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    Perkinsville, Vermont 05151
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sunny mountainview home featuring a fireplace and spacious deck1 / 24
    (1)Average
    Brownsville
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • DVD Player
    • Patio
    • Grill
    • Mountain Views
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 October 2017
    My daughter and I went on a long weekend vacation to Vermont. We rented this home for 3 nights. The location of the home has gorgeous mountain views. The day we were to arrive...
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    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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Brownsville
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Washer
    • Parking
    • Mountain Views
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a little peace and quiet in the scenic forests of Vermont? If so, you’ll love this spacious, four-bedroom Brownsville retreat that boasts a wood-burning fireplace, lovely mountain views, and space for up to eight guests! This home is located at the base of Mount Ascutney, nestled...
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    Location Information
    Brownsville, Vermont 05037
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Bridgewater
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Balcony
    • Washer
    • Terrace
    • Central Heating
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that there is another vacation rental unit on the premises, and there may be other travelers present during your stay.** Visit the scenic mountains of Vermont and stay at this 3-bedroom, 2-bathroom vacation rental apartment in Bridgewater Corners. This unit comfortably sleeps up...
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    Location Information
    Bridgewater, Vermont 05035
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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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
    • Cable/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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    Location Information
    Bridgewater, Vermont 05035
    Cabin Holiday Rental - 4 Bedrooms, 3 Bathrooms, Sleeps 24
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    Brownsville
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Mountain Views
    • Washer
    • Parking
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Travelers looking for a little peace and quiet in the forests of Vermont will adore this spacious, full-featured home away from home complete with a wood-burning fireplace, multiple living spaces, gorgeous mountain views, and room for up to 10 lucky guests making this home ideal for summertime...
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    Location Information
    Brownsville, Vermont 05037
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Grantham, NH
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Terrace
    • Parking
    • Wi-Fi
    • Grill
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very spacious 3 level stand alone condo. Inviting atmosphere for relaxation. Near West Cove beach at Eastman lake within walking distance. Great for swimming,canoeing,kayaking,sailing which can be rented through the South Cove activity center. 18 hole Championship Golf Course and thirteen tennis...
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    Grantham, New Hampshire 03753
    Condo/Apartment - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Bridgewater
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Central Heating
    • Skiing: Property Is In A Ski Resort
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that there is another vacation rental unit on the premises, and there may be other travelers present during your stay ** Leave your worries behind and stay at this 3-bedroom, 2-bathroom vacation rental apartment in Bridgewater Corners. Situated among the trees, this unit...
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    Location Information
    Bridgewater, Vermont 05035
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Grantham, NH
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Private Indoor Pool
    • DVD Player
    • Washer
    • Waterfront
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Forget all your troubles at this 3-bedroom, 2-bathroom tranquil Grantham condo. With enough room to accommodate 6 guests throughout 1,200 square feet of carefully appointed living space, this condo is a fantastic size and layout for families, friends or couples traveling together. From the spacious...
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    Location Information
    Grantham, New Hampshire 03753
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Proctorsville
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Washer
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for a quiet and secluded home for that next family vacation in Vermont, this two bedroom rental should definitely fit the bill! Enjoy a full kitchen, a gas fireplace, and comfortable living spaces, all just a few short miles from skiing, golf, hiking, fishing, and so much more....
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    Location Information
    Proctorsville, Vermont 05153
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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