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Vacation Rentals in Chester, VT and nearby

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    All 15 Rentals in the Chester Area
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    From
    $310
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    1 / 12
    Chester
    5 Bedrooms / 2 Bathrooms / Sleeps 14
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    $550
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    1 / 30
    Chester
    6 Bedrooms / 7 Bathrooms / Sleeps 18
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    $139
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    1 / 11
    Chester
    1 Bedroom / 1 Bathroom / Sleeps 5
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    $139
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    1 / 10
    Chester
    1 Bedroom / 1 Bathroom / Sleeps 4
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Internet Access
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    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
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    Location Information
    Chester, Vermont 05143
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    $119
    / Night
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    1 / 10
    Chester
    1 Bedroom / 1 Bathroom / Sleeps 2
    traveler have booked this property
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    • Air Conditioning
    • Balcony
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    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
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    Location Information
    Chester, Vermont 05143
    From
    $250
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    1 / 17
    Chester
    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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
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    Location Information
    Chester, Vermont
    From
    $200
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    1 / 21
    Chester
    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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
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    Location Information
    Chester, Vermont 05143

    The following rentals are within 10 miles of Chester, Vermont.

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    $440
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    1 / 10
    Proctorsville
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    travelers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    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
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    Location Information
    Proctorsville, Vermont 05153
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    $120
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    1 / 11
    5 of 5 stars (4) Excellent
    Saxtons River
    1 Bedroom / 1 Bathroom / Sleeps 3
    travelers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    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
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    Location Information
    Saxtons River, Vermont 05154
    5 of 5 stars Reviewed October 7, 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 August 2, 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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    $225
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    1 / 20
    4.5 of 5 stars (3) Very good
    Windham
    5 Bedrooms / 3 Bathrooms / Sleeps 10
    travelers have booked this property
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
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    Location Information
    Windham, Vermont 05359
    5 of 5 stars 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 since...
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    From
    $185
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    1 / 22
    Grafton
    1 Bedroom / 1 Bathroom / Sleeps 2
    travelers have booked this property
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    Amenities & Details
    • Grill
    • Internet Access
    • Mountain Views
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    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
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    Location Information
    Grafton, Vermont 05146
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    $310
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    1 / 16
    Perkinsville
    5 Bedrooms / 4 Bathrooms / Sleeps 12
    travelers have booked this property
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    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    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
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    Location Information
    Perkinsville, Vermont 05151
    From
    $139
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    1 / 11
    Saxtons River
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    PLEASE NOTE: Our house is rented for the winter 2010-2011. We do have availability before November 30, 2010 and after March 31, 2011. Thanks for your interest! Charming four bedroom post and beam house privately situated on a mountain and surrounded by 22 acres of its own forested land with... View all property information
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    Location Information
    Saxtons River, Vermont 05161
    From
    $650
    / Week
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    1 / 12
    Grafton
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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
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    Location Information
    Grafton, Vermont 05146
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    1 / 20
    Andover
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    • Mountain Views
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Private home for seasonal rent in Andover. $12,000 plus utilities. Call (802) 297-9400 to book today! Just 15 minutes to Okemo and 25 minutes to Stratton! Nestled in the green Mountains of southern Vermont, and surrounded by ski resorts, this custom built home completed in 2013 sits on 8 acres... View all property information
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    Location Information
    Andover, Vermont 05143