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Holiday Rentals and Homes in Chester, VT

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    Chester
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    Chester
    5 Bedrooms, 2 Bathrooms, Sleeps 14 | Quick View
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    Chester
    1 Bedroom, 1 Bathroom, Sleeps 5 | Quick View
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    Chester
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
    • Secure Parking
    • Porch
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    • Balcony
    • Air Conditioning
    • Satellite TV
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    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... View all property information
    Location Information
    Chester, Vermont 05143
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    Chester
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
    • Hot Tub
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    • Grill
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    About this property
    Classic colonial; Large white 2-story 1819 farmhouse w 5 BR, 3 B, rustic family room w/ fireplace; 2 parlors w fireplace, large eat-in kitchen, DR office w INternet WiFi; cable; phone; BR w fireplace; huge red barn w deck and hottub; lovely small river in back; beautifully furnished w period... View all property information
    Location Information
    Chester, Vermont
    Chester
    6 Bedrooms, 7 Bathrooms, Sleeps 18 | Quick View
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    • Satellite TV
    • Terrace
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    About this property
    This listing is an option for renting the entire Inn. Individual rooms can be rented as well. Please check our other listings for individual rooms. Thank you!!! Bed & Breakfast Inn and Teddy Bear and Toy Shop. The Inn - an historic Victorian residence circa 1850, is an enchanting B & B in the... View all property information
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    Chester, Vermont 05143
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    Chester
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Beautiful country cottage set on an idyllic 4 acre property, with a majestic view of the mountains, and across the street from the Tater Hill Golf course. In addition to the main house, there is a barn that can accommodate two cars and parking space for at least four additional cars. The... View all property information
    Location Information
    Chester, Vermont 05143
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    Chester
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
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    • Porch
    • Satellite TV
    • Grill
    • Waterfront
    • Washer
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    About this property
    Charming Antique Colonial/Farmhouse with 5 bedrooms, 3 full baths, two living rooms, huge dining room. Also has a great covered outdoor space (see pics, it's hard to describe), a two-acre field, frontage on the middle branch Williams River, large hay barn, covered two-car parking (and plenty of... View all property information
    Location Information
    Chester, Vermont 05143
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    4 of 5 stars (1) Very good
    Chester
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Porch
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    • Secure Parking
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    • Pet-friendly
    • Wheelchair access
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    About this property
    The Tower Room in Hugging Bear Inn and Shoppe, a bed 'n breakfast Inn. Cozy and romantic with queen-sized bed, full private bathroom with shower and air-conditioning for hot weather days. A round room (actually hexagonal) in the tower of this Victorian home overlooks the village green. Full Vermont... View all property information
    Location Information
    Chester, Vermont 05143
    4 of 5 stars Reviewed 19 July 2015
    We stay in Vermont several times a year and this time we stayed at the Hugging Bear Inn in Chester. Laura and her family are wonderful people and welcomed us into their home as...
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    Chester
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Washer
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    • Mountain Views
    • Central Heating
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    • Grill
    • Patio
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    • x
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    About this property
    We have a Classic Vermont Hillside Farmhouse. There are 5 bedrooms - all rooms can accommodate two people. One room has 2 twin beds AND a double, so 4 people could share that room. There are two full bathrooms in the house, a large kitchen, large dining room and living-room. There is also a... View all property information
    Location Information
    Chester, Vermont 05143
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    The following rentals are within 15 kilometers of Chester, Vermont.

    Grafton
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • DVD Player
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    About this property
    The vintage barn studio offers an open living plan with Queen bed, fully equipped gourmet kitchen and a cozy seating area w/ fireplace. Once an artist's studio, it is has been painstakingly renovated with a 'reduce reuse recycle' philosophy. The studio it is adorned with beautiful antique wide... View all property information
    Location Information
    Grafton, Vermont 05145
    Grafton
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Grill
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    About this property
    Enjoy a getaway situated on the brook, less than a mile from the town center of Grafton. The cabin offers a perfect place for anyone looking for a relaxing and peaceful get-away. We have designed the cabin with the goal of making it a very special place. The cabin was built in 2009 with logs from... View all property information
    Location Information
    Grafton, Vermont 05146
    Proctorsville
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
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    • Hot Tub
    • Mountain Views
    • Air Conditioning
    • Internet Access
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    • Pet-friendly
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    • Child-friendly
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    • x
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    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... View all property information
    Location Information
    Proctorsville, Vermont 05153
    1 / 24
    Andover
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Grill
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    • x
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    About this property
    Ski Okemo is 10 minutes away. Snowmobile from this new Townhouse on VAST Vermont Snowmobile Trails, hundreds of miles of marked and groomed trails. Snowmobile rentals available. Free shuttle bus to Ski Mountain across the street. Nearby XC Skiing trail, ice skating area, sledding hill, lakes with... View all property information
    Location Information
    Andover, Vermont
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    4.5 of 5 stars (3) Very good
    Windham
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
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    • Balcony
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    • Pet-friendly
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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 summer activities. GREAT ACCOMMODATIONS The Windham Country House has five large, lovely bedrooms and three... View all property information
    Location Information
    Windham, Vermont 05359
    5 of 5 stars Reviewed 23 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 since...
    5 of 5 stars Reviewed 12 January 2012
    Mary and Michael are very nice people, we spend the best time at their house. We would always recommend Windham Country House to our friends and family!
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    5 of 5 stars (4) Excellent
    Saxtons River
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • DVD Player
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    About this property
    Southeastern Vermont, near Bellows Falls, Putney, Brattleboro, across the street from Vermont Academy. Quiet, private, apartment attached to the main house. Organic garden for grazing, lovely view of the surrounding hills, classic New England village with an inn, village market, pub, four season... View all property information
    Location Information
    Saxtons River, Vermont 05154
    5 of 5 stars Reviewed 7 October 2014
    Jack and Susie's apartment was a cozy, efficient place to have as our home base for enjoying VT. It was clean, quiet, and we had fridge, stove, & microwave in case we wanted to...
    5 of 5 stars Reviewed 2 August 2014
    I've just returned from a week in Saxtons River during which I stayed at the Peters' attractive, efficient, air-conditioned, and well planned studio apartment. The double bed was...
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    1 / 30
    5 of 5 stars (2) Excellent
    Londonderry
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
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    • Mountain Views
    • Patio
    • Central Heating
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    About this property
    Welcome to The Humphreys Farmhouse, a 65-acre year-round vacation home in Vermont. Located in the heart of the Green Mountains minutes away from skiing in the winter, and hiking, swimming and many other activities in the summer, Humphreys Farm is a great place to get away from it all and have fun.... View all property information
    Location Information
    Londonderry, Vermont 05148
    5 of 5 stars Reviewed 19 March 2012
    The photos do not do this home justice. The mountain views are gorgeous and the location is superb! My family returns to this charming home year after year to enjoy the beauty...
    5 of 5 stars Reviewed 8 March 2012
    We stayed at the Humphrey's Farmhouse in august and had a great time. The home is very charming, clean and has just about every ammenity you could ask for. The house is at the...
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    Londonderry
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Washer
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    • Outdoor Dining Area
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    • Pet-friendly
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    • x
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    • x
    About this property
    House is super clean with new roof, newer carpet & newer interior paint!! Open floor plan with wood burning stove. Very clean & comfortable. Perfect for families or group of friends. Open floor plan living room, dining room & kitchen. 1 loft bedroom has king size bed w/ private bath, 1 bedroom... View all property information
    Location Information
    Londonderry, Vermont 05148
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    4.5 of 5 stars (2) Very good
    Perkinsville
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Internet Access
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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... View all property information
    Location Information
    Perkinsville, Vermont 05151
    4 of 5 stars Reviewed 10 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 house...
    5 of 5 stars Reviewed 31 July 2015
    Enjoyed the stay, hiking in the mountains, swimming in the large pool, using the tennis courts, visiting surrounding towns in New Hampshire and various areas within a 25 mile...
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    Londonderry
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
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    • Skiing: Property Is...
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    About this property
    2 Bedroom 2 Bath Ski In - Ski Out Master Bedroom Suite 1 Queen Size Bed - Master Bath Bedroom 2 Twin + 2 Twin Trundle Beds - 1 Bath Kitchen - Dining - Living Room Working Fire Place Game Room - Pool Table - Ping Pong - Foosball Sauna - Spa Walk to lifts at Magic Mountain Or Stratton Mountain... View all property information
    Location Information
    Londonderry, Vermont 05148
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    Grafton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Grafton Log Home: Charming log house in an Alpine-like meadow with great views in a peaceful setting. This home is equipped with a fireplace, eat in kitchen, dining area, 4 bedrooms (sleeps 8), 2 baths, and large deck. Internet Located about 4 miles from center of town, on a dead-end gravel... View all property information
    Location Information
    Grafton, Vermont 05146
    Andover
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    About this property
    LOG HOME 8 MILES FROM OKEMO MOUNTAIN. LOCATED ON TOP OF TERRIBLE MOUNTAIN WITH BEAUTIFUL VIEWS OF MAGIC MOUNTAIN. FULLY EQUIPPED KITCHEN, COFFEE MAKER , MICROWAVE, STOVE, REFRIGERATOR. BEDS ALL HAVE LINENS. THIS IS A TURN KEY. SLEEPS 10 IN BEDS. BEAUTIFUL AND READY TO RENT. HOLIDAY RENTALS... View all property information
    Location Information
    Andover, Vermont 05143
    Grafton
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Built circa 1840, our home, called the West Corner, is nestled in the west end of the village center, providing unusual privacy for an in village home. It is very private, yet only a minute's walk to the main street, village park & the tavern, the general store and churches. Grafton is a very... View all property information
    Location Information
    Grafton, Vermont 05145