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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.
    16 Matching Rentals in the Winchester AreaView all 27 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.
    Affordable Spacious Vacation Home on Lake Spofford1 / 16
    (4)Excellent
    Chesterfield
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Beautiful House overlooking Spofford Lake1 / 40
    (32)Very good
    Spofford
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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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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    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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    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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    Spofford, New Hampshire 03462
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Richmond
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Balcony
    • Mountain Views
    • Wi-Fi
    • Washer
    • Patio
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This historic home on 24 wooded acres in New Hampshire about 20 minutes south of Keene was built in 1774 and occupied by a Revolutionary War family. Additions over the centuries make it a rich experience of history, nature, fireplaces and wood-burning stoves, rich furnishings, and modern amenities!...
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    Richmond, New Hampshire 03470
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    Amenities & Details
    • Mountain Views
    • DVD Player
    • Cable/satellite TV
    • Porch
    • Wi-Fi
    • Patio
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2015
    We rented this house to be close to Mount Snow so our boys could spend their vacation snowboarding. The house was as beautiful as described. The rooms were charming and...
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    About this property
    • 19th Century Farmhouse with beautiful mature gardens • 24 Park like acres - woods and streams • Perfect location to attend Marlboro Music Festival • Close to Brattleboro (10 miles) located in the Village of West Halifax • House has 4 bedrooms - 2 master bedrooms with Queen Beds • 2...
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    Location Information
    West Halifax, Vermont 05358
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    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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    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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    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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    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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    Jaffrey
    6 Bedrooms, 8 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Washer
    • Balcony
    • Porch
    • Patio
    • Grill
    • Mountain Views
    • Internet Access
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1) Beautiful historic property, originally an early 1800's tavern with a rich history as a working farm, seasonal vacation home, inn and year round residence. Property sits at the base of Mt. Monadnock with beautiful mountain and pastoral views. Our street address is Mountain Rd., 2) One of...
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    Location Information
    Jaffrey, New Hampshire 034526002
    Holiday Rental House - 6 Bedrooms, 8 Bathrooms, Sleeps 12
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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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    Keene
    9 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • 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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