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Vacation Rentals in Chester, VT and nearby

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    All 20 Rentals in the Chester Area
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    From
    $119
    / Night
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    1 / 10
    4 of 5 stars (1) Very good
    Chester
    1 Bedroom / 1 Bathroom / Sleeps 2
    other traveler has booked this property
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    From
    $550
    / Night
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    1 / 30
    Chester
    6 Bedrooms / 7 Bathrooms / Sleeps 18
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    From
    $310
    / Night
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    1 / 12
    Chester
    5 Bedrooms / 2 Bathrooms / Sleeps 14
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    From
    $139
    / Night
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    1 / 11
    Chester
    1 Bedroom / 1 Bathroom / Sleeps 5
    Overview Make Inquiry
    Amenities & Details
    • Refrigerator
    • Secure Parking
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Balcony
    • Satellite TV
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    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... View all property information
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    Location Information
    Chester, Vermont 05143
    From
    $139
    / Night
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    1 / 10
    Chester
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Secure Parking
    • Porch
    • Balcony
    • Internet Access
    • Refrigerator
    • Air Conditioning
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    From
    $200
    / Night
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    1 / 8
    Chester
    4 Bedrooms / 3 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Satellite TV
    • Deck
    • Washer
    • Dryer
    • Stereo System
    • Internet Access
    • Central Heating
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
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    Location Information
    Chester, Vermont 05143
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    $200
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    1 / 21
    Chester
    5 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Washer
    • Satellite TV
    • Fireplace
    • Waterfront
    • Stereo System
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    From
    $250
    / Night
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    1 / 17
    Chester
    5 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Fireplace
    • Deck
    • Stereo System
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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

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

    From
    $275
    / Night
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    1 / 20
    4.5 of 5 stars (3) Very good
    Windham
    5 Bedrooms / 3 Bathrooms / Sleeps 10
    other travelers have booked this property
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Internet Access
    • DVD Player
    • Washer
    • Stereo System
    • Satellite TV
    • Air Conditioning
    • Deck
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    $120
    / Night
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    1 / 11
    5 of 5 stars (4) Excellent
    Saxtons River
    1 Bedroom / 1 Bathroom / Sleeps 3
    other travelers have booked this property
    Overview Reviews (4) Make Inquiry
    Amenities & Details
    • Linens Provided
    • Refrigerator
    • Internet Access
    • Air Conditioning
    • Stove
    • Mountain Views
    • DVD Player
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • 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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    From
    $300
    / Night
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    1 / 15
    Londonderry
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Make Inquiry
    Amenities & Details
    • Grill
    • Stove
    • Deck
    • Garage
    • Washer
    • Satellite TV
    • Refrigerator
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • 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
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    Location Information
    Londonderry, Vermont 05148
    From
    $332
    / Night
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    1 / 16
    Perkinsville
    5 Bedrooms / 4 Bathrooms / Sleeps 12
    other travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Internet Access
    • Central Heating
    • Mountain Views
    • Deck
    • DVD Player
    • Private Outdoor...
    • Satellite TV
    • Fireplace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    $350
    / Night
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    1 / 13
    Londonderry
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    other travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Internet Access
    • Satellite TV
    • Parking
    • Air Conditioning
    • Linens Provided
    • Stove
    • Refrigerator
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Quaint New England town located in the lush Green Mountains of Vermont. Wonderful year round activities. A great winter sports area, downhill skiing, snow boarding, sledding, ice skating, cross country skiing, snowmobiling, and horse draw sleigh rides. Only minutes to Stratton, Bromley, Okemo and... View all property information
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    Location Information
    Londonderry, Vermont 05148
    From
    $175
    / Night
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    1 / 22
    5 of 5 stars (2) Excellent
    Londonderry
    3 Bedrooms / 1 Bathroom / Sleeps 8
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Stereo System
    • Washer
    • Satellite TV
    • Mountain Views
    • Fireplace
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    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
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    Location Information
    Londonderry, Vermont 05148
    From
    $1,800
    / Night
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    1 / 23
    Cavendish
    6 Bedrooms / 6 Bathrooms / Sleeps 14
    Overview Make Inquiry
    Amenities & Details
    • Mountain Views
    • Skiing: Property Is...
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Hot Tub
    • TV
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    Glimmerstone Mansion is on the National Historic Registery built in 1845 and completely restored in 2012. The property is located within 4 miles of Okemo Mountain Ski Resort. Stunning for a wedding, special event or a large luxurious property for multi-family or large party ski vacations. The... View all property information
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    Location Information
    Cavendish, Vermont 05142
    From
    $440
    / Night
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    1 / 10
    Proctorsville
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    other travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • DVD Player
    • Satellite TV
    • Stereo System
    • Deck
    • Hot Tub
    • Mountain Views
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • 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
    From
    $185
    / Night
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    1 / 22
    Grafton
    1 Bedroom / 1 Bathroom / Sleeps 2
    other travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • TV
    • Water Views
    • Grill
    • Mountain Views
    • Internet Access
    • Waterfront
    • Deck
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • 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
    From
    $650
    / Week
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    1 / 12
    Grafton
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • DVD Player
    • Stereo System
    • Washer
    • Fireplace
    • Central Heating
    • Satellite TV
    • Deck
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    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
    From
    $139
    / Night
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    1 / 11
    Saxtons River
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Fireplace
    • Dryer
    • DVD Player
    • Satellite TV
    • Central Heating
    • Grill
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
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    1 / 20
    Andover
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Mountain Views
    • Satellite TV
    • DVD Player
    • Dishwasher
    • Wi-Fi
    • Parking
    • Fireplace
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Private home for seasonal rent in Andover. $15,000 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
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