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Chester House Rentals

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    Don't let other travellers get your favourite Chester area vacation rental. You're so close to securing your perfect getaway. Book today.
    13 Matching Rentals in the Chester AreaView all 20 rentals
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    Chester
    5 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    The following rentals are within 15 kilometres of Chester.
    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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    Amenities & Details
    • 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 December 10, 2018
    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 December 8, 2018
    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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    Grafton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Amenities & Details
    • 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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    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 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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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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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    Location Information
    Proctorsville, Vermont 05153
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Proctorsville
    5 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • 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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    Amenities & Details
    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    Suitability
    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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    Location Information
    Grafton, Vermont 05146
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    Amenities & Details
    • Internet Access
    • DVD Player
    • Balcony
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 23, 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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    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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    Location Information
    Proctorsville, Vermont 05153
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Cavendish
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Location Information
    Cavendish, Vermont 05142
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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