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Holiday Rentals in Winchester, NH

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    ₹ 9,515 Average
    ₹ 67,000+
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    1 / 21
    Winchester
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Winchester
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Winchester
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    The following rentals are within 25 kilometres of Winchester, New Hampshire.

    Colrain, MA
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • Waterfront
    • Central Heating
    • Shared Garden
    • Wi-Fi
    • Outdoor Dining Area
    • Mountain Views
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This eco-friendly, river front home in Colrain, Massachusetts is situated in a slice of rural paradise, yet close to the charming village of Shelburne Falls and year-round recreational activities. The house is situated on 2.9 acres of flatland and wooded path down to the beach edge of the North... View all property information
    Location Information
    Colrain, Massachusetts 01340
    1 / 7
    5 of 5 stars (5) Excellent
    Guilford, VT
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Outdoor Dining Area
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Washer
    • Parking
    • Mountain Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Schoolhouse No. 10 is a fully renovated 18th century schoolhouse in scenic southern Vermont. Located on a country road in a very special neighborhood, the Schoolhouse offers a romantic private getaway for one or two couples, or a creative art spa for friends who want to come share an historic... View all property information
    Location Information
    Guilford, Vermont 05301
    5 of 5 stars Reviewed 25 October 2014
    A beautifully restored schoolhouse with abundant charm. The owners Susan and Gilbert are genuinely the nicest people you could meet. The refrigerator was stocked with farm fresh...
    5 of 5 stars Reviewed 7 October 2013
    My husband and I just returned from a glorious fall weekend in VT. Schoolhouse No. 10 is situated on a quiet country dirt road and far exceeded all expectations. The Schoolhouse...
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    Colrain, MA
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Mountain Views
    • Secure Parking
    • Wi-Fi
    • Outdoor Dining Area
    • Central Heating
    • Grill
    • DVD Player
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    This is a NEW Place being offered. Come and delight in this laid back, serene spot and then write my 1st review! This is a lovely fragrance free, efficiency apartment off the back wing of my rural home and Studio/Gallery. Very private, quiet, light-filled, clean cozy and spacious with pastoral... View all property information
    Location Information
    Colrain, Massachusetts 01340
    1 / 16
    Chesterfield
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Waterfront
    • Internet Access
    • Satellite TV
    • Grill
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    A beautiful recently remodeled 3 bedroom 2.5 bath house with a full living room including a beautiful, efficient pellet stove in the living room and adjoining covered deck with a stunning view of the lake, a separate area for the dining room, a kitchen with refrigerator, stove, microwave and... View all property information
    Location Information
    Chesterfield, New Hampshire 03462
    1 / 15
    5 of 5 stars (1) Excellent
    Marlborough
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Parking
    • Mountain Views
    • Central Heating
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Even better than the pictures! Spring photos coming! On 5 acres & surrounded by nature. The unobstructed views are magnificent. Our favorite trail to Mt. Monadnock is about a 10 min walk from the house. Approximately 1 hr 45 min drive from Boston!<BR>We have a king size bed in one bedroom, full... View all property information
    Location Information
    Marlborough, New Hampshire 03455
    5 of 5 stars Reviewed 2 weeks ago
    This house was a pleasant surprise. Large, comfortable, clean, great location with a wonderful view of the mountain. This house is a bargain. If you are looking for a comfortable...
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    1 / 6
    Marlborough
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ref # 364404 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Come home to this cozy and warm two bedroom, one bathroom furnished apartment. It is... View all property information
    Location Information
    Marlborough, New Hampshire
    1 / 5
    Marlborough
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ref # 364416 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. Come and have a wonderful stay in this tasteful one bedroom, one bathroom furnished... View all property information
    Location Information
    Marlborough, New Hampshire
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    Richmond
    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Balcony
    • Mountain Views
    • Wi-Fi
    • Washer
    • Patio
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • 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!... View all property information
    Location Information
    Richmond, New Hampshire 03470
    1 / 6
    Marlborough
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ref # 364421 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. This property is situated on 14 acres of naturally wooded land, Our apartment community... View all property information
    Location Information
    Marlborough, New Hampshire
    1 / 6
    Marlborough
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Ref # 364422 Because we focus on monthly rentals, we do not accept bookings with a gap between move in date and availability date. We generally require move in dates to be within 7 days of the availability date. This property is situated on 14 acres of naturally wooded land, Our apartment community... View all property information
    Location Information
    Marlborough, New Hampshire
    Fitzwilliam
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Mountain Views
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Washer
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-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.... View all property information
    Location Information
    Fitzwilliam, New Hampshire 03447
    1 / 40
    5 of 5 stars (1) Excellent
    Spofford
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Waterfront
    • Washer
    • Porch
    • Internet Access
    • Satellite TV
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Spofford, New Hampshire 03462
    5 of 5 stars Reviewed 29 October 2015
    We booked this house for our out-of-town friends for the second year in a row, and are so glad we did. Spending time with our friends here was such a treat. The house is large...
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    1 / 5
    5 of 5 stars (4) Excellent
    Guilford, VT
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Guilford, Vermont 05301
    5 of 5 stars 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 (who needs...
    5 of 5 stars Reviewed 4 December 2013
    When we first booked it we were not excepting anything that great for the price. Just wanted to get away for thanksgiving with the kids and try something different. The weather...
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    Richmond
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Patio
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Enjoy a quiet entire apartment with your friend and family in historic town Richmond,Va This is a apartment on first floor in byrd park area with all renovation, it is between byrd park and Cary town (good neighborhood) first floor apartment has a 1 year lease tenant live there. it is pretty... View all property information
    Location Information
    Richmond, New Hampshire 23220
    1 / 2
    Spofford
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Satellite TV
    • Porch
    • Waterfront
    • Parking
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    cottage on spofford lake with shuffle board court. Sandy beach for small children. Large shaded area for eating out. great place to relax on vacation. Docking for boats. Beds: 1 Queen Bed, 1 Double Bed, 2 Twin Beds View all property information
    Location Information
    Spofford, New Hampshire 03462
    1 / 5
    4 of 5 stars (1) Very good
    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
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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.... View all property information
    Location Information
    Brattleboro, Vermont 05301
    4 of 5 stars Reviewed 2 weeks ago
    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 we'd...
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    Fitzwilliam
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Central Heating
    • Grill
    • Waterfront
    • Washer
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Come to MountainShadow for an escape from stress and the city! Our location is perfect for summer outdoor activities, blueberry picking, mountain hiking, fall foliage and visiting farms for organic meat, pork, lamb, eggs, maple syrup, apples, and cider. We are on Scott Pond and in the shadow of... View all property information
    Location Information
    Fitzwilliam, New Hampshire 03447
    Get the List
    Fitzwilliam
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Central Heating
    • Patio
    • Mountain Views
    • Waterfront
    • Wi-Fi
    • Washer
    • Grill
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    (Please note that the FlipKey 'per night' quote is for a weekly rental and their "Ready to book?" quote does not include the security deposit amount.) We book Sunday to Sunday. If we are not booked within three weeks of a date, then we open up to partial week rentals. Our minimal rental is 2... View all property information
    Location Information
    Fitzwilliam, New Hampshire 03447
    Hinsdale
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • DVD Player
    • Grill
    • Central Heating
    • Washer
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    Owners present a newly renovated, private, mountaintop apartment tucked back in the wood. Conveniently located, come enjoy the wilderness, hikes, wildlife, bonfires, and waterfall all on the property! Feel free to get dirty, we have in-unit private washer/dryer and a private bath, or kickback... View all property information
    Location Information
    Hinsdale, New Hampshire 03451
    Richmond
    2 Bedrooms, 3 Bathrooms, Sleeps 3 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    Stunningly beautiful two bedroom, t.5 bath condominium in the Oregon Hill section of Richmond, along the James River within easy walking access to the Canal Walk, numerous restaurants and with the heart of downtown Richmond less than five minutes away; walk if you feel like it. Rents fully... View all property information
    Location Information
    Richmond, New Hampshire 23220