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Holiday Rentals in Charlestown

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    ₹ 11,103 Average
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    ₹ 0₹ 69,000+
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    Don't let other travellers get your favourite Charlestown area holiday home. You're so close to securing your perfect getaway. Book today.
    All 17 Rentals in Charlestown
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    The following rentals are within 15 kilometres of Charlestown.
    Lake Warren-Alstead-Walpole-Keene- Spring Summer1 / 40
    (11)Excellent
    Alstead
    4 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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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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    A Beautiful farmhouse with homemade breakfast!1 / 51
    (1)Excellent
    Perkinsville, VT
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Secluded, Spectacular House with Mount Ascutney Vi1 / 20
    (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)
    • 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
    Perkinsville, Vermont 05151
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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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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    Amenities & Details
    • 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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    Location Information
    Chester, Vermont 05143
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
    • 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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    Location Information
    Chester, Vermont 05143
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Perkinsville, VT
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    Chester, VT
    6 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Cable/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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    Location Information
    Chester, Vermont 05143
    Private Room - 6 Bedrooms, 7 Bathrooms, Sleeps 18
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    Chester, VT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Grafton, VT
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Central Heating
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Patio
    • Grill
    • Mountain Views
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Find a home-away-from-home hidden in the trees when you venture to this 2-bedroom, 1-bathroom vacation rental house that sleeps up to 6 guests in Grafton! Architecturally designed and beautifully unique, this cottage is a picture-perfect scene, secluded from the bustle of the big city so you can...
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    Location Information
    Grafton, Vermont 05146
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Perkinsville, VT
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    Chester, VT
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick 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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    Chester, Vermont 05143
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Chester, VT
    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
    Chester, Vermont 05143
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Perkinsville, VT
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    Chester, VT
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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
    Chester, Vermont 05143
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Chester, VT
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Skiing: Property Is In A Ski Resort
    • Central Heating
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 5-bedroom, 1.5-bath vacation rental house in Chester provides a charming farmhouse setting for up to 8 guests. Nestled on 13 acres shared with Gordon's Christmas Tree Farm, this scenic property dazzles you with natural beauty during every season! See if the fish bite at the nearby river or...
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    Location Information
    Chester, Vermont 05143
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Grafton, VT
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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
    Grafton, Vermont 05146
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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