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Chester Holiday Homes

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    All 26 Rentals in Chester
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    Chester is popular with travellers just like you. Don’t let them get your perfect place first—book today!
    Chester
    6 Bedrooms, Sleeps 18Quick View
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    Chester
    1 Review
    1 Bedroom, Sleeps 2Quick View
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    Chester
    1 Review
    5 Bedrooms, Sleeps 14Quick View
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    Chester
    2 Reviews
    1 Bedroom, Sleeps 2Quick View
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    • Washer
    • Satellite TV
    • Mountain Views
    • Central Heating
    • DVD Player
    • Wi-Fi
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 13 October 2016
    Like your grandparents' old vacation home, full of funky furniture but comfortable and homey. The public areas are vast, with two dining areas seating 6-8 each and a living room...
    Excellent of 5 bubbles
    Reviewed 14 September 2016
    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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    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...
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    Location Information
    Chester, Vermont 05143
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Chester
    3 Bedrooms, Sleeps 8Quick View
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Chester, Vermont 05143
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Chester
    3 Bedrooms, Sleeps 6Quick View
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    • Wi-Fi
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Chester, Vermont 05143
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Chester
    1 Bedroom, Sleeps 5Quick View
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    Amenities & Details
    • Balcony
    • Terrace
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Porch
    • Satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Chester, Vermont 05143
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Chester
    1 Bedroom, Sleeps 4Quick View
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    • Terrace
    • Secure Parking
    • Porch
    • Internet Access
    • Balcony
    • Air Conditioning
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Chester, Vermont 05143
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Chester
    3 Bedrooms, Sleeps 8Quick View
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    • Grill
    • Patio
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The 1843 Stone House is a pre-civil war home that is quaint and comfortable for 2 families or 3 couples. The house is full of charm while also providing modern amenities. The Chester Village green is a short walk from the house where shops and restaurants are housed in buildings from yesteryear....
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    Chester, Vermont 05143
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Chester
    3 Bedrooms, Sleeps 6Quick View
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    Amenities & Details
    • Washer
    • Parking
    • Mountain Views
    • Internet Access
    • Private Garden
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Carriage House is less than a mile to charming Chester Village-enjoy quaint restaurants and pubs, antique shops, art galleries, and a country market. Explore southern Vermont’s famous hiking trails, world class skiing, farms, winding rivers and breweries (near Harpoon & Long Trail) Close...
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    Location Information
    Chester, Vermont 05143
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    The following rentals are within 15 kilometres of Chester.
    Perkinsville
    4 Reviews
    5 Bedrooms, Sleeps 12Quick View
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    Amenities & Details
    • Internet Access
    • Central Heating
    • Mountain Views
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Very good of 5 bubbles
    Reviewed 30 March 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...
    Very good of 5 bubbles
    Reviewed 11 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...
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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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    Londonderry
    2 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    • DVD Player
    • Wi-Fi
    • Washer
    • Grill
    • Satellite TV
    • Mountain Views
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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....
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    Location Information
    Londonderry, Vermont 05148
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Grafton
    1 Bedroom, Sleeps 2Quick View
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Grafton, Vermont 05146
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Londonderry
    3 Bedrooms, Sleeps 6Quick View
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    Amenities & Details
    • Central Heating
    • Internet Access
    • Parking
    • Outdoor Dining Area
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Find peace and tranquility in all seasons at ‘West River Lodge,’ a warm and cozy 3-bedroom, 1-bathroom vacation rental log cabin, with accommodations for 6 in the Vermont woods. With 3.5 acres of private woodlands and a great location, minutes from the town of Londonderry, this cabin is the perfect...
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    Location Information
    Londonderry, Vermont 05148
    Cabin Holiday Rental - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Londonderry
    3 Bedrooms, Sleeps 7Quick View
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    Amenities & Details
    • Washer
    • Internet Access
    • Grill
    • Satellite TV
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Londonderry, Vermont 05148
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Grafton
    1 Review
    2 Bedrooms, Sleeps 4Quick View
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    • Washer
    • DVD Player
    • Central Heating
    • Wi-Fi
    • Patio
    • Secure Parking
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 13 February 2017
    We stayed in this home for a weekend ski vacation. Though the sleeping areas were a little tight for our family of 5 there was plenty of living space for relaxing. The home is...
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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...
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    Location Information
    Grafton, Vermont 05146
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Grafton
    4 Reviews
    4 Bedrooms, Sleeps 8Quick View
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    Amenities & Details
    • Mountain Views
    • Satellite TV
    • Grill
    • Washer
    • Internet Access
    • Central Heating
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 24 October 2016
    I would recommend this lovely home to anyone who wants to get away to the country and not worry about the fast pace of life for a few days. There is WiFI but no phone service...
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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...
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    Grafton, Vermont 05146
    Cabin Holiday Rental - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Grafton
    1 Bedroom, Sleeps 2Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Shared Garden
    • Mountain Views
    • Internet Access
    • Waterfront
    • Parking
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Grafton, Vermont 05146
    Cabin Holiday Rental - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Proctorsville
    3 Bedrooms, Sleeps 10Quick View
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    • DVD Player
    • 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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    Proctorsville, Vermont 05153
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Windham
    3 Reviews
    5 Bedrooms, Sleeps 10Quick View
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    • Internet Access
    • DVD Player
    • Balcony
    • Washer
    • Satellite TV
    • Air Conditioning
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Excellent of 5 bubbles
    Reviewed 24 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...
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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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    Windham, Vermont 05359
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Perkinsville
    1 Bedroom, Sleeps 2Quick View
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    • Grill
    • Air Conditioning
    • DVD Player
    • Washer
    • Mountain Views
    • Housekeeping Included
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Perkinsville, Vermont 05151
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Cavendish
    6 Bedrooms, Sleeps 17Quick View
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    • Satellite TV
    • Patio
    • Hot Tub
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The property includes 7 bedrooms (robes, bath amenities, tempurpedic beds, fireplaces, vable television, DVD and ensuite baths in all but 2), 8-person hot tub, dining for 24. Great for large groups or big families or specialb events. Warm weather Rustic Barn with bar can seat up to 115 guest...
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    Cavendish, Vermont 05142
    Holiday Rental House - 6 Bedrooms, 10 Bathrooms, Sleeps 17
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    Perkinsville
    1 Bedroom, Sleeps 2Quick View
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    • Mountain Views
    • Grill
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Housekeeping Included
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Perkinsville, Vermont 05151
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Grafton
    4 Bedrooms, Sleeps 8Quick View
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    • 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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    Perkinsville
    3 Bedrooms, Sleeps 8Quick View
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    • DVD Player
    • Washer
    • Air Conditioning
    • Grill
    • Mountain Views
    • Housekeeping Included
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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,...
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    Perkinsville, Vermont 05151
    Private Room - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Perkinsville
    1 Bedroom, Sleeps 2Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Housekeeping Included
    • Washer
    • Grill
    • Mountain Views
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Perkinsville, Vermont 05151
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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