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Holiday Apartments 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!
    All 25 Rentals in Chester
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    Classic Vermont Farmhouse1 / 12
    (1)Excellent
    Chester
    5 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Chester
    6 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    Vermont Farmhouse Rooms to share1 / 10
    (2)Excellent
    Chester
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Washer
    • Cable/satellite TV
    • Mountain Views
    • Central Heating
    • DVD Player
    • Wi-Fi
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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
    05143, Chester, Vermont
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick 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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    05143, Chester, Vermont
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Hugging Bear Inn - Tower Room1 / 10
    (1)Very good
    Chester
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Porch
    • Air Conditioning
    • Terrace
    • Balcony
    • DVD Player
    • Cable/satellite TV
    • Secure Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 July 2015
    We stay in Vermont several times a year and this time we stayed at the Hugging Bear Innin Chester. Laura and her family are wonderful people and welcomed us into their home as...
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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...
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    05143, Chester, Vermont
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Chester
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Balcony
    • Terrace
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Porch
    • Cable/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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    05143, Chester, Vermont
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Chester
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • 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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    05143, Chester, Vermont
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Chester
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick 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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    Location Information
    05143, Chester, Vermont
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Chester
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Terrace
    • Secure Parking
    • Porch
    • Internet Access
    • Balcony
    • Air Conditioning
    • Cable/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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    Location Information
    05143, Chester, Vermont
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    The following rentals are within 15 kilometres of Chester.
    Log Cabin With Views1 / 13
    (5)Excellent
    Grafton
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Mountain Views
    • Cable/satellite TV
    • Grill
    • Washer
    • Wi-Fi
    • Central Heating
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 September 2017
    This was a last minute rental and the owner Gina was very accommodating. Great place to bring the family and spend quality time together. We played board games and watched...
    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 10) 2 baths, and large deck. Internet Located about 4 miles from center of town, on a dead-end gravel...
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    Location Information
    05146, Grafton, Vermont
    Cabin Holiday Rental - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Andover
    2 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Secure Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are seeking to get away from the craziness of everyday life and take in natural beauty and the enjoyment of downhill and cross country skiing, snowshoeing, hiking, antique shopping, and cool resturants you found the right spot. Close to: Okemo, Bromley, Killington, Jackson Gore, and Magic...
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    Location Information
    05143, Andover, Vermont
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 10
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    Secluded, Spectacular House with Mount Ascutney Vi1 / 20
    (4)Very good
    Perkinsville
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Internet Access
    • Central Heating
    • Mountain Views
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 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...
    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
    05151, Perkinsville, Vermont
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Proctorsville
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    • DVD Player
    • Washer
    • Wi-Fi
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedrooms, 2 full Bathrooms, Sleeps 6 adults with 2 sofa sleepers for children This house is 5 miles from Okemo skiing. Nearby are VAST snowmobile trails. There shuttle service from house to Okemo Mountain so you don't have to deal with parking. Killington Mt is 18 miles. Nearby snowmobile...
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    05153, Proctorsville, Vermont
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Proctorsville
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Washer
    • Central Heating
    • Mountain Views
    • DVD Player
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedrooms, 1 Bathroom, Sleeps 6 has Sofa Bed for kids. This home is located 5 miles from Okemo Mountain. Okemo is a great family resort for skiing. If its snowmobile trails you are looking for the house is near VAST Trails. Also there is snowmobile rental about 1 mile away. There is a shuttle...
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    Location Information
    05153, Proctorsville, Vermont
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Proctorsville
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Cable/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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    Location Information
    05153, Proctorsville, Vermont
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Cavendish
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is less then 10 minutes to the base of Okemo Mountain yet it's in a secluded quiet development. This spacious home has 4 bedrooms and 2 1/2 baths. There is plenty of seating in the kitchen and dining room. There are TV's int he family room as well as the master bedroom and one queen...
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    05142, Cavendish, Vermont
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Large, Lovely, Affordable Mountain Home1 / 20
    (3)Very good
    Windham
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • DVD Player
    • Balcony
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    05359, Windham, Vermont
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Grafton
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Internet Access
    • Parking
    • Grill
    • Washer
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This modern 4-bedroom, 3-bathroom Vermont vacation rental home comfortably accommodates 8 guests in 3,800 square feet of luxury. The authentic, newly renovated 1950's farmhouse offers a quintessential homestead experience, nestled in the Green Mountains of Southern Vermont on stunning, lush...
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    Location Information
    05146, Grafton, Vermont
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cavendish
    6 Bedrooms, 10 Bathrooms, Sleeps 17 Quick View
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    • Cable/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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    Location Information
    05142, Cavendish, Vermont
    Holiday Rental House - 6 Bedrooms, 10 Bathrooms, Sleeps 17
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    Perkinsville
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick 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
    05151, Perkinsville, Vermont
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Grafton
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/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
    05146, Grafton, Vermont
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Perkinsville
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick 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
    05151, Perkinsville, Vermont
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Perkinsville
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick 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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    Location Information
    05151, Perkinsville, Vermont
    Private Room - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Perkinsville
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick 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
    05151, Perkinsville, Vermont
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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