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Winchester Vacation Rentals

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    All 25 Rentals in Winchester
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    Winchester
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Beautiful Lake Side Getaway, Quiet, and Peaceful1 / 21
    (4)Excellent
    Winchester
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Winchester
    1 Bedroom, 1 Bathroom, Sleeps 2 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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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Grill
    • Internet Access
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 1, 2016
    This is a beautiful house, fully equipped with everything you could possibly need. The lake was beautiful and very peaceful. The owners were extremely accommodating and helpful.
    Reviewed September 9, 2016
    This house had everything we needed, including accessibility for somebody using a walker or cane. The downstairs had very nice appliances, bathroom and a porch that we spend 99...
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    About this property
    This dream vacation house is literally on the water where everyone wants to be! It is by far the best that Lake Spofford could offer! Cooking for the family is a breeze in the full kitchen with stove, refrigerator, microwave, dishwasher and a view of the lake at all times. You can even watch TV or...
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    Location Information
    Spofford, New Hampshire 03462
    Holiday Rental House - 4 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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    • Internet Access
    • Washer
    • Grill
    • Porch
    • Mountain Views
    • DVD Player
    • Central Heating
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 17, 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 June 11, 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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    New Salem, Massachusetts 01355
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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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 January 16, 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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    South Newfane, VT
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • 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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    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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    Romantic Vermont Vacation Cabin with View1 / 24
    (4)Excellent
    Newfane, VT
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Parking
    • Grill
    • Washer
    • Mountain Views
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 17, 2018
    We had a wonderful time at the house & surrounding area! It was clean & very quiet! It’s a beautiful house tucked away in the woods! We loved all the flea markets &amp...
    Reviewed October 14, 2017
    Loved our quiet two days in this very private cabin. It has everything needed for a short getaway. We enjoyed fires in the wood stoves and the complete quiet!
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    About this property
    At 'Ridgeview' you can go to sleep to the flicker of a wood stove, wake up to sunshine streaming through tall windows onto honey-colored pine flooring, and watch from your deck as sunlight fills the river valley and plays across the ridge opposite. Beautiful newer construction of 1000 square...
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    Location Information
    Newfane, Vermont 05345
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Vermont Log Cabin available for weekend and weekly1 / 5
    (7)Excellent
    Guilford, VT
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 12, 2017
    Beautiful mountain retreat! Has all of the comforts of home minus wifi and cell service. A perfect way to unwind and disconnect. Pictures do not do this quaint log cabin...
    Reviewed May 30, 2014
    The word "cabin" doesn't do this property justice. It is actually a comfortable two bedroom log home which is immaculate and well secluded. There is no internet service...
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    About this property
    If you want to get away from the hustle and bustle of our technologically driven lives and slow down, breath and relax, our cabin is the perfect place for you. No phones, television or internet, just a nice comfortable and affordable country log cabin nestled in the foothills of the Green...
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    Location Information
    Guilford, Vermont 05301
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    South Newfane, VT
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Skiing: Property Is In A Ski Resort
    • Hot Tub
    • Mountain Views
    • Patio
    • Washer
    • DVD Player
    • Central Heating
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Adams Hill House is a European-style luxury estate, consisting of 4 bedrooms, 6 bathrooms and 11 acres of grounds. It abuts several thousand acres of managed woodlot with many trails for mountain biking and cross country skiing. The property has beautiful long range views to the west and south....
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    Location Information
    South Newfane, Vermont 05351
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    Adorable Studio apartment in Brattleboro1 / 5
    (2)Average
    Brattleboro, VT
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Central Heating
    • Outdoor Dining Area
    • Grill
    • Shared Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 9, 2016
    You can't beat the location just off I-91, 5 minutes (15 if you walk) from downtown Brattleboro. The hosts were very nice and helpful, and we loved their cats and dog, when...
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    About this property
    Welcome to the Culbertson House! This adorable studio apartment was completely refinished a few years ago. It features a gorgeous stone fireplace, tasteful furnishings and decoration, a comfortable king-size bed, fully equipped kitchen, full bath with shower, and exquisite hardwood walls and floor....
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    Location Information
    Brattleboro, Vermont 05301
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Newfane, VT
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • 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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    West Dummerston, VT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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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    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 March 20, 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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    • 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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    Rindge
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Called 'A little slice of heaven' by one renter, this scenic property captures the beauty of rural New England. The cabin is a modernized 1903 cottage with 1100 square feet of comfortable living space that includes three bedrooms, living room, dining room, kitchen and one full bathroom. Fully...
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    Location Information
    Rindge, New Hampshire 03461
    Cabin Holiday Rental - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Classic New England Farm House1 / 12
    (1)Excellent
    Chesterfield
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 17, 2017
    Very attractive room and surroundings. The room was clean and affordable. The bed was very comfortable. The bathroom was very clean. The pets became our friends in the short...
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    About this property
    Located in forested New Hampshire close to the big city ( fifteen minutes ). Quiet and beautiful The 1780 Farm is a walk away from New Hampshires 13 thousand acre Pisga State Park with miles of groomed Cross County ski and snowmobiling trails. There is hiking in Madam Sherii's Forest and Mount...
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    Location Information
    Chesterfield, New Hampshire 03443
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Keene
    9 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    • 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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    Greenfield, MA
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Terrace
    • Housekeeping Included
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brandt House is a three-and-a-half-acre, turn-of-the-century estate located in a charming residential area of Greenfield, just minutes from I-91 and Route 2 in northwestern Massachusetts. Walking distance to downtown Greenfield and in the northern Pioneer Valley where culture, history, adventure,...
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    Location Information
    Greenfield, Massachusetts 01301
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Newfane, VT
    7 Bedrooms, 6 Bathrooms, Sleeps 20 Quick View
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    • 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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    Newfane, Vermont 05345
    Holiday Rental House - 7 Bedrooms, 6 Bathrooms, Sleeps 20
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    Chesterfield
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Air Conditioning
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on The 1780 Farm's 35 scenic acres this is a classic New England farm on a quiet street which connects to Pisga State park, New Hampshires largest state park containing miles of groomed trails for cross country skiing or snowmobiling or just a hike through idyllic New England forests....
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    Location Information
    Chesterfield, New Hampshire 03443
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Westmoreland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • 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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