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Winchester Vacation Rentals

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    Don't let other travellers get your favourite Winchester area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 20 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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    The following rentals are within 30 kilometres of Winchester.
    West Dummerston, VT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Fitzwilliam
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Mountain Views
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Internet Access
    • 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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    Fitzwilliam, New Hampshire 03447
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Vermont Log Cabin available for weekend and weekly1 / 5
    (6)Excellent
    Guilford, VT
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 May 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 30 May 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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    Harrisville
    6 Bedrooms, 5 Bathrooms, Sleeps 15 Quick View
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    Amenities & Details
    • Internet Access
    • Mountain Views
    • DVD Player
    • Outdoor Dining Area
    • Porch
    • Washer
    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    750 Acre (300 Hectare) Estate! 5 Bedrooms + Detached Unit - 4.5 Baths - (Sleeps 14-15) This enormous estate is one of a kind! The rental includes the a Main House, the Sunset/Guest Cabin, secret Treehouse, and private land larger than many towns! Although the estate is often enjoyed for...
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    Location Information
    Harrisville, New Hampshire 03450
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 15
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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 9 July 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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    Romantic Vermont Vacation Cabin with View1 / 20
    (3)Excellent
    Newfane, VT
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Parking
    • Grill
    • Washer
    • Mountain Views
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 October 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!
    Reviewed 25 October 2016
    This 1000 sq ft cabin, which was first rented in 2004, is in a quiet, wooded area with a fantastic view of fall leaves, both near and far. The first floor bed was very...
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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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    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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    Location Information
    Richmond, New Hampshire 03470
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    Affordable Spacious Vacation Home on Lake Spofford1 / 16
    (3)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
    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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    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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    Lakefront Cottage1 / 24
    (3)Very good
    Rindge
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Waterfront
    • Cable/satellite TV
    • Parking
    • Outdoor Dining Area
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 August 2016
    First, the owner is wonderful. Second, the cottage is right on beautiful, quiet Pearly Lake. I was here for 4 weeks in July and the lake was always peaceful. You can swim to...
    Reviewed 15 October 2015
    My husband & I had the pleasure of staying in this sweet cabin with our three kids (five, three and one). We absolutely loved our stay! The sun sparkling on the lake each...
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    About this property
    Here is the perfect location for your family vacation or a couple's getaway. Pearly Pond offers all of your favorite outdoor activities. Choose from swimming, canoeing (kayaking), hiking, mountain biking or fishing. If you're more into relaxing, just stretch out on the deck with your favorite...
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    Location Information
    Rindge, New Hampshire 03461
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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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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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Grill
    • Internet Access
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 November 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 9 September 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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    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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    Classic New England Farm House1 / 12
    (1)Excellent
    Chesterfield
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 August 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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    Greenfield, MA
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • 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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    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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    Putney, VT
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Parking
    • Housekeeping Included
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Grill
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The home is situated on a beautiful 46 acre estate that is joined with conservation land. You are on top of the hill with views of New Hampshire Hills.The first floor offers living room with propane heat. The large windows adjoin the seating area that seats 6. There is a new kitchen with a stove,...
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    Location Information
    Putney, Vermont 05346
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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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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