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Vacation Rentals in Chester, VT and nearby

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    1 / 12
    5 of 5 stars (1) Excellent
    Chester
    5 Bedrooms, 2 Bathrooms, Sleeps 14 | Quick View
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    1 / 10
    4 of 5 stars (1) Very good
    Chester
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 30
    Chester
    Private Room, 7 Bathrooms, Sleeps 18 | Quick View
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    1 / 10
    5 of 5 stars (1) Excellent
    Chester
    Private Room, 2 Bathrooms, Sleeps 2 | Quick View
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    • Washer
    • Satellite TV
    • Mountain Views
    • Central Heating
    • DVD Player
    • Wi-Fi
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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
    5 of 5 stars Reviewed 1 week ago
    This was my first visit to the Okemo area in the summer (have skied several times) and I was looking for a place stay while I did some hiking and mountain biking. The farmhouse...
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    1 / 22
    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Parking
    • Private Yard
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Amare Guesthouse is a relaxed and inviting recently restored Victorian home steps from downtown Chester VT. From coffee to cocktails relax on one of the large porches. Walking distance to restaurants and pubs, rivers, farms, trails, antique shops, galleries, and a grocery store.  Enjoy small... View all property information
    Location Information
    Chester, Vermont
    1 / 11
    Chester
    Private Room, 1 Bathroom, Sleeps 5 | Quick View
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    • Balcony
    • Terrace
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Porch
    • Satellite TV
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Chester, Vermont
    1 / 13
    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Charming 1820 stone house, The Cairn, just off Rte 103 in a small village enclave reached by crossing the historic Bartonsville covered bridge- rebuilt after hurricane Irene. The house is surrounded by a lovely garden that reaches down to the Williams River in the back. The main floor has an open... View all property information
    Location Information
    Chester, Vermont
    1 / 10
    Chester
    Private Room, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
    • Secure Parking
    • Porch
    • Internet Access
    • Balcony
    • Air Conditioning
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Chester, Vermont
    1 / 23
    Chester
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Porch
    • Satellite TV
    • Grill
    • Waterfront
    • Washer
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Chester, Vermont
    1 / 17
    Chester
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Grill
    • Patio
    • Washer
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Chester, Vermont
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    1 / 8
    Chester
    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Chester, Vermont

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

    1 / 16
    4.5 of 5 stars (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...
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    Perkinsville, Vermont
    4 of 5 stars 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...
    4 of 5 stars 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 house...
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    1 / 10
    Proctorsville
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
    • Satellite TV
    • Washer
    • Patio
    • Hot Tub
    • Mountain Views
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    Location Information
    Proctorsville, Vermont
    1 / 22
    5 of 5 stars (2) Excellent
    Londonderry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Wi-Fi
    • Washer
    • Grill
    • Satellite TV
    • Mountain Views
    • Patio
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Londonderry, Vermont
    1 / 14
    Grafton
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • DVD Player
    • Central Heating
    • Wi-Fi
    • Patio
    • Secure Parking
    • Grill
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    1 / 34
    Grafton
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Grill
    • DVD Player
    • Shared Yard
    • Mountain Views
    • Internet Access
    • Waterfront
    • Parking
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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
    Location Information
    Grafton, Vermont
    1 / 31
    Perkinsville
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • DVD Player
    • Central Heating
    • Housekeeping...
    • Grill
    • Mountain Views
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Come and enjoy a beach view in VT! refreshing yourself in a lovely beach painting room. Our place is a 200 year old farmhouse which is located in a big farm scenic private area in Perkinsville, Vermont. We have a covered bridge at one end of our road. It's quiet dirt road which is perfect for... View all property information
    Location Information
    Perkinsville, Vermont
    1 / 20
    4.5 of 5 stars (3) Very good
    Windham
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Internet Access
    • DVD Player
    • Balcony
    • Washer
    • Satellite TV
    • Air Conditioning
    • Grill
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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.<BR><BR>GREAT ACCOMMODATIONS<BR>The Windham Country House has five large, lovely bedrooms... View all property information
    Location Information
    Windham, Vermont
    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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    1 / 19
    Grafton
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
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    • Shared Yard
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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
    1 / 23
    Andover
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Wi-Fi
    • Central Heating
    • Secure Parking
    • Mountain Views
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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
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    1 / 16
    Londonderry
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Washer
    • Internet Access
    • Grill
    • Satellite TV
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    1 / 40
    Perkinsville
    Private Room, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
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    • Mountain Views
    • Washer
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    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    A beautiful bed and breakfast Vermont getaway! with 3 comfortable bedrooms available. Our place is a 200 year old farmhouse which is located in a big farm scenic private area in Perkinsville, Vermont. We have a covered bridge at one end of our road. It's quiet dirt road which is perfect for biking,... View all property information
    Location Information
    Perkinsville, Vermont
    1 / 34
    Perkinsville
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Washer
    • Mountain Views
    • Grill
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    You will definitely love this classic, unique, beautiful and comfortable studio room. It's a great space for your vocation. Our place is a 200 year old farmhouse which is located in a big farm scenic private area in Perkinsville, Vermont. We have a covered bridge at one end of our road. It's quiet... View all property information
    Location Information
    Perkinsville, Vermont
    1 / 32
    Perkinsville
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Central Heating
    • Grill
    • Washer
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    • DVD Player
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    A cozy and comfortable room with the sun shines all day! It is an opened bright space with big windows all around. Our place is a 200 year old farmhouse which is located in a big farm scenic private area in Perkinsville, Vermont. We have a covered bridge at one end of our road. It's quiet dirt road... View all property information
    Location Information
    Perkinsville, Vermont
    1 / 11
    Grafton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Private Yard
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Grafton, Vermont
    1 / 12
    Grafton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • DVD Player
    • Balcony
    • Grill
    • Internet Access
    • Central Heating
    • Washer
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    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