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Holiday Rentals in Charlestown

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    ₹ 14,617 Average
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    ₹ 0₹ 65,000+
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    All 26 Rentals in Charlestown
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    The following rentals are within 15 kilometres of Charlestown.
    Lake Warren-Alstead-Walpole-Keene- Fall Foliage Rates1 / 20
    (10)Excellent
    Alstead
    4 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Chester, VT
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    3 BDR Farmhouse on Tranquil 105 acre Organic Farm1 / 15
    (1)Excellent
    Walpole
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Secluded, Spectacular House with Mount Ascutney Vi1 / 21
    (4)Very good
    Perkinsville, VT
    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)
    • 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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    Perkinsville, Vermont 05151
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Chester, VT
    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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    Chester, Vermont 05143
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Hugging Bear Inn - Tower Room1 / 10
    (1)Very good
    Chester, VT
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Porch
    • Air Conditioning
    • Terrace
    • Balcony
    • DVD Player
    • 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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    Chester, Vermont 05143
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Classic Vermont Farmhouse1 / 12
    (1)Excellent
    Chester, VT
    5 Bedrooms, 2 Bathrooms, Sleeps 14 Quick View
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    • Mountain Views
    • Central Heating
    • DVD Player
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Washer
    • Patio
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2016
    Clean, cozy, comfortable. The house was a lot larger than we expected, as was the backyard. It sort of just opens up to a great view of a few peaks in the distance. There is a...
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    About this property
    CLASSIC VERMONT HILLTOP FARMHOUSE - 5 BEDROOMS SLEEP UP TO 12 PEOPLE. GREAT FOR FAMILY & GROUP GET TOGETHERS. SECLUDED, YET WITHIN 1 HOUR'S DRIVING DISTANCE TO 6 MAJOR SKI/RECREATIONAL AREAS – OKEMO IS 8 MILES AWAY. Private and secluded, yet less than 8 miles to the Okemo Mountain resort and...
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    Chester, Vermont 05143
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 14
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    Chester, VT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick 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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    Log Cabin With Views1 / 13
    (5)Excellent
    Grafton, VT
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Mountain Views
    • Satellite TV
    • Grill
    • Washer
    • Wi-Fi
    • Central Heating
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    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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    Grafton, Vermont 05146
    Cabin Holiday Rental - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Chester, VT
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick 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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    Vermont Farmhouse Rooms to share1 / 10
    (2)Excellent
    Chester, VT
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Washer
    • 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 13 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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    Chester, Vermont 05143
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Chester, VT
    1 Bedroom, 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
    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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    Luxurious Historic Home in the Heart of Grafton1 / 14
    (1)Excellent
    Grafton, VT
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Central Heating
    • Wi-Fi
    • Patio
    • Secure Parking
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 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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    Grafton, Vermont 05146
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Perkinsville, VT
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Chester, VT
    6 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    • Satellite TV
    • Terrace
    • Air Conditioning
    • Balcony
    • DVD Player
    • Porch
    • Internet Access
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This listing is an option for renting the entire Inn. Individual rooms can be rented as well. Please check our other listings for individual rooms. Thank you!!! Bed & Breakfast Inn and Teddy Bear and Toy Shop. The Inn - an historic Victorian residence circa 1850, is an enchanting B & B in the...
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    Chester, Vermont 05143
    Private Room - 6 Bedrooms, 7 Bathrooms, Sleeps 18
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    Perkinsville, VT
    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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    Perkinsville, Vermont 05151
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Chester, VT
    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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    Chester, Vermont 05143
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Walpole
    8 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
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    • Internet Access
    • Satellite TV
    • Washer
    • Air Conditioning
    • Sauna
    • DVD Player
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rochambeau Lodge is a comfortably rustic renovated barn situated inAlyson's Orchard. It is filled with country furnishings that give it a unique and unforgettable charm. Rochambeau overlooks the beautiful Walpole countryside. Inside, you will find a fully equipped kitchen with a gorgeous 12-foot...
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    Walpole, New Hampshire 03608
    Holiday Rental House - 8 Bedrooms, 3 Bathrooms, Sleeps 18
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    Walpole
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Outdoor Dining Area
    • Washer
    • Grill
    • DVD Player
    • Internet Access
    • Satellite TV
    • Mountain Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The West Wing of the Caleb Foster Farm House (1860) is truly a wonder. This impeccably restored property recently underwent a complete renovation and features exceptional architectural detailing by local artisans. You will find lovely antiques and fine artwork in each room, as well as gorgeous...
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    Walpole, New Hampshire 03608
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Walpole
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Mountain Views
    • Washer
    • Internet Access
    • Satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a more casual atmosphere? The East Wing of the Caleb Foster Farm House (1860) just might be your style. The first floor features rooms that openly flow into one another, including a full kitchen with a dining table and a spacious, sunny living room that’s equipped with a full...
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    Walpole, New Hampshire 03608
    Private Room - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Perkinsville, VT
    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
    Perkinsville, Vermont 05151
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Perkinsville, VT
    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
    Perkinsville, Vermont 05151
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Grafton, VT
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick 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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    Grafton, VT
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • 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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    Grafton, Vermont 05146
    Cabin Holiday Rental - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Grafton, VT
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick 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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    Grafton, Vermont 05146
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Grafton, VT
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • Internet Access
    • Parking
    • Grill
    • Washer
    • Air Conditioning
    • Patio
    • 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
    Grafton, Vermont 05146
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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