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Windsor House Rentals

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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.
    23 Matching Rentals in the Windsor AreaView all 34 rentals
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    The following rentals are within 25 kilometers of Windsor.
    Hakuna Matata1 / 28
    (1)Very good
    Bridgewater
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    Proctorsville
    3 Bedrooms, 2 Bathrooms, Sleeps 10 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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    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 October 2017
    We went to VT with another couple to visit our son and booked "The Farmhouse". The house is decorated beautifully, and has comfortable furniture and beds. It was very...
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    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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    South Pomfret, Vermont 05067
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Newport, NH
    1 Bedroom, 1 Bathroom, Sleeps 2 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 2
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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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    A house with a view: gorgeous home with a spectacular view of the mountains.1 / 53
    (1)Excellent
    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
    Reviewed 13 July 2018
    Claudia and Jeff's place is amazing - it's set on a quiet, beautiful spot on a hill; it has a sweeping, unobstructed view of the surrounding mountains; it's only a mile or so...
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    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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    Village Farmhouse - mins to GMHA, Okemo, Killington. Pet-friendly.1 / 27
    (1)Excellent
    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
    Reviewed 20 October 2018
    Are you looking for a true Vermont experience? Look no further than this comfortable, quaint, relaxing village farm house, with 4 bedrooms. Sleeps 8. We enjoyed walking in the...
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    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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    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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    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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    Location Information
    Proctorsville, Vermont 05153
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    Proctorsville
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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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    Proctorsville, Vermont 05153
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    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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    Location Information
    Bridgewater, Vermont 05035
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    Sunny mountainview home featuring a fireplace and spacious deck1 / 31
    (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 16 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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    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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    Location Information
    Proctorsville, Vermont 05143
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 14
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    Proctorsville
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Parking
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This budget-friendly and recently updated 1920s condo is located on the Villiage Green and is just five miles from Okemo and everything it has to offer. There is an open floor plan through the kitchen, dining room, and living room, so it's easy to socialize with your group. The vintage ski...
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    Location Information
    Proctorsville, Vermont 05153
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Cavendish
    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Parking
    • Cable/satellite TV
    • Hot Tub
    • Washer
    • Internet Access
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Find a quintessential Vermont escape at this bright and inviting home in Cavendish, a peaceful retreat among the evergreens with beautiful exposed beams and natural wood details. Spend your days skiing, snowboarding, snowshoeing, or hiking, and return home to luxuriate in the private hot tub on the...
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    Location Information
    Cavendish, Vermont 05142
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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    Bridgewater
    7 Bedrooms, 4 Bathrooms, Sleeps 22 Quick View
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    • Private Garden
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated in 2015 by Fortune Cookie Design of Boston, this modern farmhouse is one of a kind. You won't find another vacation rental with this quality, design & natural beauty. If you are sick of bunk-bed ski house dives, you'll think you've died & gone to heaven in this hip farmhouse....
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    Location Information
    Bridgewater, Vermont 05035
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 22
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    South Pomfret
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Central Heating
    • Wi-Fi
    • Patio
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled on a bucolic hillside just 3 miles north of downtown Woodstock, this inviting, bright home is a magical place to gather. It's truly the perfect place to recharge after a day of skiing and exploring! The clean, well-maintained vacation rental offers 3 bedrooms, 2 bathrooms, and...
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    South Pomfret, Vermont 05091
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Vermont 1828 Reunion House, sleeps 20, 5 miles to Okemo1 / 20
    (3)Excellent
    Proctorsville
    8 Bedrooms, 4 Bathrooms, Sleeps 20 Quick View
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    • Washer
    • Parking
    • Central Heating
    • Grill
    • Patio
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 days ago
    The 1828 Reunion House helped us create lasting memories from the slopes to home. This charming home is the perfect fit for anyone! For those who like to bask in the beauty of...
    Reviewed 1 week ago
    I have been to Vermont 1828 Reunion House for 3 years. Each visit consisted of many friends gathering to reconnect and celebrate friendship while experience what Vermont has to...
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    About this property
    The Vermont 1828 Reunion House is a Historic Farmhouse 5 miles from Okemo Mountain Resort. Featuring 8 bedrooms, 4 baths, 2 kitchens, 2 living rooms, and sleeping for 20, Bed linens and towels are provided by our housekeeping pros. This is the place for Making Memories with Friends and Family in...
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    Location Information
    Proctorsville, Vermont 05143
    Holiday Rental House - 8 Bedrooms, 4 Bathrooms, Sleeps 20
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