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Holiday Rentals in Chesterfield

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    Don't let other travellers get your favourite Chesterfield area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 20 Rentals in Chesterfield
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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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    Classic New England Farm House1 / 12
    (1)Excellent
    Chesterfield
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Chesterfield
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    The following rentals are within 25 kilometers of Chesterfield.
    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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    Winchester
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Stunning Lakefront home on crystal clear, sandy bottomed, 110 acre Forest Lake at the junction of NH,VT,& MA will be your long awaited retreat in the whispering pines, shimmering lakes, and beautiful foliage of New Hampshire. Bring the kids & dogs or just enjoy by yourselves. The Great room with...
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    Location Information
    Winchester, New Hampshire 03470
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    Romantic Vermont Vacation Cabin with View1 / 24
    (4)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 17 October 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 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!
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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 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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    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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    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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    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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    Brattleboro, Vermont 05301
    Condo/Apartment - 1 Bathroom, Sleeps 2
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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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    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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    3 BDR Farmhouse on Tranquil 105 acre Organic Farm1 / 15
    (1)Excellent
    Walpole
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Balcony
    • Internet Access
    • Washer
    • Air Conditioning
    • Mountain Views
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 August 2013
    The farmhouse is fully equipped as advertised, and very comfortable and quiet. Our family especially enjoyed the kittens, the cattle, and the lovely surroundings. We we were...
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    About this property
    Our three-bedroom farmhouse is completely stocked including washer/dryer, dishwasher, satellite TV, complimentary wifi, farmer’s porch with rocking chairs, gas grill, picnic table, fire pit, hiking trails, and more. It’s a perfect retreat for week-long vacations, family reunions/getaways,...
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    Location Information
    Walpole, New Hampshire 03608
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    Keene
    9 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • 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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    Winchester
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Grill
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private one bedroom on the site of The Outlaw Brewing Company. Enjoy the country life while enjoying locally made craft beer. Lots to do for adventerous couples. Visit local breweries, distilleries and wineries. Hike Pisgah State Park, Mount Monadnock, Madame Sherri's Forest or Pulpit Falls. Make...
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    Winchester, New Hampshire 03470
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Amenities & Details
    • 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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    Location Information
    Winchester, New Hampshire 03470
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    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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