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Winchester Holiday 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.
    All 17 Rentals in Winchester
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    Winchester
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Stay at a Craft Brewery1 / 17
    (1)Excellent
    Winchester
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Winchester
    4 Bedrooms, 2 Bathrooms, Sleeps 9 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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    • Internet Access
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Grill
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 September 2014
    Great off the beaten track place to stay yet only 20 minutes from Keene. Bill and Sandie very gracious hosts both before and during your stay. Accommodations very modern. We...
    Reviewed 12 July 2014
    My fiancé and another couple stayed here for a few days in May. It was absolutely beautiful and exactly what we were looking for! My fiancé and I are avid "outdoors...
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    About this property
    New Hampshire Meals & Rentals Operator's License #063697 2 Bedrooms, 1 bath, sleeps 6. Private beach, dock, raft, rowboat, canoe, 5 Kayaks, or launch your boat. Cable TV, high speed internet, WIFI, 42' flat screen internet TV. Sleeps 6 - two bedrooms - One with Queen Bed, one with two single beds...
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    Winchester, New Hampshire 03470
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Beautiful Lakefront Cottage with Gorgeous Views1 / 10
    (13)Excellent
    Winchester
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • DVD Player
    • Air Conditioning
    • Internet Access
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Winchester, New Hampshire 03470
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
    Winchester
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Internet Access
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Winchester, New Hampshire 03470
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    The following rentals are within 25 kilometres of Winchester.
    Beautiful House overlooking Spofford Lake1 / 92
    (32)Very good
    Spofford
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • 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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    Spofford, New Hampshire 03462
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Fitzwilliam
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • 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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    Fitzwilliam, New Hampshire 03447
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Vermont Log Cabin available for weekend and weekly1 / 5
    (8)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 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
    Steps to the sandy beach1 / 36
    (1)Excellent
    Spofford
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • 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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    Adorable Studio apartment in Brattleboro1 / 5
    (2)Average
    Brattleboro, VT
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • 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
    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
    Featuring 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
    Troy
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Mountain Views
    • Hot Tub
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Inquire today For Year Round vacations! 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...
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    Location Information
    Troy, New Hampshire 03447
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    Affordable Spacious Vacation Home on Lake Spofford1 / 102
    (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 20 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
    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 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
    Northfield, MA
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely, large (360 sq. ft) quiet, private entry ground-floor studio, with private bathroom with shower, in 3-story post-&-beam home on pine-clad hilltop, offered by award-winning composer, author & healer. Parking by house, looking out upon 3 & 1/2 acres of tranquil pine forest. Fridge &...
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    Northfield, Massachusetts 01360
    Condo/Apartment - 1 Bathroom, Sleeps 4
    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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