We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

West Chesterfield Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    $367 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite West Chesterfield area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 18 Rentals in West Chesterfield
    Sort by:
    Default
    The following rentals are within 25 kilometres of West Chesterfield.
    Winchester
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Vermont Log Cabin available for weekend and weekly1 / 5
    (6)Excellent
    Guilford, VT
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Adorable Studio apartment in Brattleboro1 / 5
    (2)Average
    Brattleboro, VT
    Studio, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    West Dummerston, VT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    West Dummerston, Vermont 05357
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Richmond
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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!...
    View all property information
    Location Information
    Richmond, New Hampshire 03470
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Affordable Spacious Vacation Home on Lake Spofford1 / 16
    (3)Excellent
    Chesterfield
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Chesterfield, New Hampshire 03462
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    Romantic Vermont Vacation Cabin with View1 / 20
    (3)Excellent
    Newfane, VT
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    See all reviews
    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...
    View all property information
    Location Information
    Newfane, Vermont 05345
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Steps to the sandy beach1 / 26
    (1)Excellent
    Spofford
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Spofford, New Hampshire 03462
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Walpole
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • Washer
    • Grill
    • DVD Player
    • Internet Access
    • Cable/satellite TV
    • Mountain Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The West Wing of the Caleb Foster Farm House (1860) is truly a wonder. This impeccably restored property recently underwent a complete renovation and features exceptional architectural detailing by local artisans. You will find lovely antiques and fine artwork in each room, as well as gorgeous...
    View all property information
    Location Information
    Walpole, New Hampshire 03608
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Make Enquiry
    Walpole
    8 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Sauna
    • DVD Player
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rochambeau Lodge is a comfortably rustic renovated barn situated inAlyson's Orchard. It is filled with country furnishings that give it a unique and unforgettable charm. Rochambeau overlooks the beautiful Walpole countryside. Inside, you will find a fully equipped kitchen with a gorgeous 12-foot...
    View all property information
    Location Information
    Walpole, New Hampshire 03608
    Holiday Rental House - 8 Bedrooms, 3 Bathrooms, Sleeps 18
    Make Enquiry
    Save time - get the best West Chesterfield rentals sent straight to your email!
    Get the List
    Walpole
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Mountain Views
    • Washer
    • Internet Access
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a more casual atmosphere? The East Wing of the Caleb Foster Farm House (1860) just might be your style. The first floor features rooms that openly flow into one another, including a full kitchen with a dining table and a spacious, sunny living room that’s equipped with a full...
    View all property information
    Location Information
    Walpole, New Hampshire 03608
    Private Room - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    3 BDR Farmhouse on Tranquil 105 acre Organic Farm1 / 15
    (1)Excellent
    Walpole
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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...
    See all reviews
    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,...
    View all property information
    Location Information
    Walpole, New Hampshire 03608
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Beautiful House overlooking Spofford Lake1 / 40
    (32)Very good
    Spofford
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    See all reviews
    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
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Beautiful Lake Side Getaway, Quiet, and Peaceful1 / 21
    (4)Excellent
    Winchester
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    See all reviews
    About this property
    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 (can be made into Queen), and a full size pullout couch in...
    View all property information
    Location Information
    Winchester, New Hampshire 03470
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    South Newfane, VT
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    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....
    View all property information
    Location Information
    South Newfane, Vermont 05351
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
    Make Enquiry
    Classic New England Farm House1 / 12
    (1)Excellent
    Chesterfield
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    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...
    See all reviews
    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...
    View all property information
    Location Information
    Chesterfield, New Hampshire 03443
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Putney, VT
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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,...
    View all property information
    Location Information
    Putney, Vermont 05346
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Chesterfield
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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....
    View all property information
    Location Information
    Chesterfield, New Hampshire 03443
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    List your property
    Owner log in