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Winchester House Rentals

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    Don't let other travellers get your favourite Winchester area holiday rental. You're so close to securing your perfect getaway. Book today.
    15 Matching Rentals in the Winchester AreaView all 26 rentals
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    Winchester
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    The following rentals are within 30 kilometres of Winchester.
    Beautiful House overlooking Spofford Lake1 / 40
    (32)Very good
    Spofford
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    PARADISE on EARTH! - Historic 4BR Farmhouse1 / 7
    (1)Excellent
    West Halifax, VT
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Stone 'n Sky Lodge on an Ancient Stone Landscape1 / 32
    (5)Excellent
    New Salem, MA
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Internet Access
    • Washer
    • Grill
    • Porch
    • Mountain Views
    • DVD Player
    • Central Heating
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2017
    Great accomodations for a whole bunch of people. Four bedrooms with beds for 10 PLUS additional mattresses for the kids. Fresh eggs and coffee from the hosts were a nice treat...
    Reviewed 11 June 2017
    We visited New Salem for 5 days in the end of May. We were welcomed by a cheerful Sarah carrying a carton of organic eggs from her farm next door. Obviously a good start! For a...
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    About this property
    Gorgeous, spacious, red-oak post and beam home on 11.25 acres abutting 2,700 acre Wildlife Preserve. 3-5 bedroom, 3 bath, 2600 sq ft, fully furnished and appointed, Stone 'n Sky Lodge offers extraordinary privacy and local convenience. Located on a paved, town-maintained, dead-end road surrounded...
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    Location Information
    New Salem, Massachusetts 01355
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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    South Newfane, VT
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Secure Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect house on the top of the mountain overlooking the mountains with amazing views. Enjoy sunrises and sunsets from most of the rooms and the patio. Total privacy but close to everything. House was built by a renowned architect using only the best natural materials. You will enjoy a very large...
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    Location Information
    South Newfane, Vermont 05351
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Fitzwilliam
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in peaceful private comfort on 1.5 acres on serene 110 acre Rockwood Pond. The view out the full length deck across the lake will make it easy to fully enjoy the Great Room with cathedral ceilings, wood stove, new appliances and lots of seating and the Private Hot Tub under the stars. 3...
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    Location Information
    Fitzwilliam, New Hampshire 03447
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    West Dummerston, VT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Central Heating
    • Grill
    • Internet Access
    • Cable/satellite TV
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I bought this church from the Roman Catholic Diocese almost twelve years ago. The stained glass is original and is illuminated each morning by the sunrise coming up over Black Mtn. This stunning space is the result of a three year renovation. The curved walls and archways create a true sanctuary...
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    Location Information
    West Dummerston, Vermont 05357
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Newfane, VT
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our private Estate is overlooking the mountains and fun for every occasion, close to Stratton Mountain and Mount Snow. It is ideal for winter retreat and summer enjoyment near the pool. The estate offer endless opportunities for a group of friends or family. The house has 6 bedrooms. It also...
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    Location Information
    Newfane, Vermont 05345
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    Affordable Spacious Vacation Home on Lake Spofford1 / 40
    (4)Excellent
    Chesterfield
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Waterfront
    • Internet Access
    • Mountain Views
    • Patio
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2018
    This house was beautiful. Very spacious and clean. It was so easy to make yourself at home. Tony was great at communicating and was very helpful when needed. I recommend this...
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    About this property
    A beautiful recently remodeled 3 bedroom 2.5 bath house, large living room with an adjoining covered deck with a BBQ that has a stunning view of the lake, a dining room, & a fully equipped kitchen. The master bedroom has it's own private bath & a sunning deck overlooking the lake. The 2 other...
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    Location Information
    Chesterfield, New Hampshire 03462
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Spofford
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The cottage provides guests with 250 feet of private shoreline and spectacular sunsets. A swimmer's delight, Lake Spofford received the State's highest rating for clean water in 2005.Sitting on the south shore of the lake, it offers terrific sunfish and bass fishing. It's a great lake for other...
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    Location Information
    Spofford, New Hampshire 03462
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    West Halifax, VT
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Garden
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful house interior and out. Many rooms for privacy including TV room, pool table below, dining areas, living room with circular couch to sit around open glass wood stove and a small library, computer space. Dining room open to kitchen area and to living room. Upper balcony and outside...
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    Location Information
    West Halifax, Vermont 05358
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Steps to the sandy beach1 / 26
    (1)Excellent
    Spofford
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Waterfront
    • Washer
    • Grill
    • Patio
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A charming just remodeled 3 bedroom 2.5 bath house with a full eat-in kitchen, with modern appliances, kitchen table & chairs with direct view of the deck & lake, wide open to the living room with a comfortable sleeper couch, 55 in curved TV with plenty of DTV channels to choose & a pellet stove...
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    Location Information
    Spofford, New Hampshire 03462
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Keene
    9 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    • Skiing: Property Is In A Ski Resort
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Boasting over 6,500 square feet of living space with 9 bedrooms and 6.5 bathrooms, this vacation rental home in Keene is the ideal location for groups of up to 18! The Colonial home was originally constructed in 1880 and has been renovated by designer Kylee Trunck. During your stay, take a dip in...
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    Location Information
    Keene, New Hampshire 03431
    Holiday Rental House - 9 Bedrooms, 7 Bathrooms, Sleeps 18
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    Newfane, VT
    7 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our private Estate is overlooking the mountains and fun for every occasion, close to Stratton Mountain and Mount Snow. It is ideal for winter retreat and summer enjoyment near the pool. Main house and Guest/Game house offer endless opportunities for a group of friends or family. The main house has...
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    Location Information
    Newfane, Vermont 05345
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 20
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    Westmoreland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape the hustle and bustle of daily life and discover a wonderful New England getaway at this 2-bedroom, 1-bathroom vacation rental house for up to 4 guests. Resting on 2.5 acres just outside Westmoreland with distant, woody views, this family home boasts a rustic-meets-modern, 1,500-square-foot...
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    Location Information
    Westmoreland, New Hampshire 03467
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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