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Chester Holiday Homes

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    Don't let other travellers get your favourite Chester area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 27 Rentals in Chester
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    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Hugging Bear Inn - Tower Room1 / 10
    (1)Very good
    Chester
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Chester
    6 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    Chester
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Secure Parking
    • Porch
    • Internet Access
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A room with calming earth tones. This is a medium sized room with one queen and one full double bed, private bathroom with shower and air-conditioning for hot weather days. This listing is an option for renting an individual room in the Inn. The entire Inn can be rented as well. Please check our...
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    Chester, Vermont 05143
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Chester
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Balcony
    • Terrace
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Porch
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Overlooking the village green, this bright and spacious room accommodates a family or group of people. Has two queen-sized beds and a love-seat sleeper sofa with a twin bed. Has wall-to-wall carpeting, private bath with shower and air conditioning for hot weather days. Also features a infrared...
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    Chester, Vermont 05143
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Chester
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Parking
    • Mountain Views
    • Internet Access
    • Private Garden
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Carriage House is less than a mile to charming Chester Village-enjoy quaint restaurants and pubs, antique shops, art galleries, and a country market. Explore southern Vermont’s famous hiking trails, world class skiing, farms, winding rivers and breweries (near Harpoon & Long Trail) Close...
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    Chester, Vermont 05143
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Patio
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The 1843 Stone House is a pre-civil war home that is quaint and comfortable for 2 families or 3 couples. The house is full of charm while also providing modern amenities. The Chester Village green is a short walk from the house where shops and restaurants are housed in buildings from yesteryear....
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    Chester, Vermont 05143
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Chester
    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Central Heating
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 5-bedroom, 1.5-bath vacation rental house in Chester provides a charming farmhouse setting for up to 8 guests. Situated on 13 acres shared with Gordon's Christmas Tree Farm, this scenic property dazzles you with natural beauty during every season! See if the fish bite at the nearby river or...
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    Chester, Vermont 05143
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 8
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    The following rentals are within 15 kilometres of Chester.
    Secluded, Spectacular House with Mount Ascutney Vi1 / 20
    (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)
    • 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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    Perkinsville, Vermont 05151
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Windham
    6 Bedrooms, 4 Bathrooms, Sleeps 18 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a picturesque, rustic contemporary 5000 sq. ft. home on 15 acres with a private drive. The location is 5 miles from Magic Mountain, 15 miles from Stratton, 16 miles from Bromely, and 17 miles from Okemo. VAST trails are a few hundred yards away for snowmobiles and walking. There are 5...
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    Windham, Vermont 05359
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 18
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    Proctorsville
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • 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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    Modern cabin in the woods - upscale seclusion in tranquil setting, dogs welcome!1 / 31
    (1)Very good
    Windham
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Cable/satellite TV
    • Washer
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2018
    Having worked hard for a year on our new house in New Hampshire, my wife and I decided to unwind for a couple of days at this wooded cabin in Vermont for our 36h Wedding...
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    About this property
    If the mountains of Vermont are calling your name, come stay in this beautiful, modern cabin in the woods and revel in its superb blend of upscale design and quiet, tranquil seclusion. You can bring along your beloved dog, as well, for a small nightly fee! You'll be nestled in tall evergreens,...
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    Windham, Vermont 05359
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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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
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Proctorsville
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    Windham
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience a Vermont vacation from the pages of a magazine at this three-bedroom Windham home, a secluded country house with an open living space, an expansive deck and yard, and nearby access to picturesque villages, hiking trails, and ski slopes! This home sits on a grassy, tree-lined property...
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    Location Information
    Windham, Vermont 05359
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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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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    Location Information
    Cavendish, Vermont 05142
    Holiday Rental House - 6 Bedrooms, 10 Bathrooms, Sleeps 17
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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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    Andover
    2 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Secure Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are seeking to get away from the craziness of everyday life and take in natural beauty and the enjoyment of downhill and cross country skiing, snowshoeing, hiking, antique shopping, and cool resturants you found the right spot. Close to: Okemo, Bromley, Killington, Jackson Gore, and Magic...
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    Andover, Vermont 05143
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 10
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    Large, Lovely, Affordable Mountain Home1 / 20
    (3)Very good
    Windham
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • DVD Player
    • Balcony
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 June 2014
    First of all, I want to thank Mary for being very friendly in providing us with information and details on getting to their house. We (group of 7) did not get to meet them...
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    About this property
    The Windham Country House, a spacious contemporary home, sits on a secluded country road, providing you with peace, privacy and beautiful scenery, while being near many of southern Vermont's activities. GREAT ACCOMMODATIONS The Windham Country House has five large, lovely bedrooms and three full...
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    Location Information
    Windham, Vermont 05359
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Grafton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cute Vermont farmhouse is just 10 minutes to Magic, 20 minutes to Bromley and 25 minutes to Stratton. On the main level there is the master bedroom with a full bath, kitchen, dining, and large living area with a comfortable fireplace and a bonus woodstove to keep you extra warm during those...
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    Grafton, Vermont 05146
    Holiday Rental House - 4 Bedrooms, 2 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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    Grafton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Step back in time when you stay at this authentic, newly renovated 1950’s farmhouse nestled in the Green Mountains of Southern Vermont! This modern 3-bedroom, 2-bath Vermont vacation rental home offers a quintessential homestead experience for up to 8 guests throughout 2,700 square feet of luxury....
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    Location Information
    Grafton, Vermont 05146
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Grafton
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Patio
    • Grill
    • Mountain Views
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Find a home-away-from-home hidden in the trees when you venture to this 2-bedroom, 1-bathroom vacation rental house that sleeps up to 6 guests in Grafton! Architecturally designed and beautifully unique, this cottage is a picture-perfect scene, secluded from the bustle of the big city so you can...
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    Location Information
    Grafton, Vermont 05146
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    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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    Cavendish, Vermont 05142
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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    Vermont 1828 Reunion House, sleeps 20, 5 miles to Okemo1 / 20
    (2)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 2 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 4 days 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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