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.
TripAdvisor
Chesterfield
Post
Inbox
Search

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
    Location
    Any Distance
    from
    Price
    per night
    C$260 Average
    |||
    |||
    C$0C$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Chesterfield area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 18 Rentals in Chesterfield
    Sort by:
    Default
    Affordable Spacious Vacation Home on Lake Spofford1 / 102
    (4)Excellent
    Chesterfield
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Classic New England Farm House1 / 12
    (1)Excellent
    Chesterfield
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Chesterfield
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    The following rentals are within 25 kilometres of Chesterfield.
    Beautiful House overlooking Spofford Lake1 / 46
    (32)Very good
    Spofford
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travellers have 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 November 1, 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 September 9, 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
    Steps to the sandy beach1 / 36
    (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
    Winchester
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Winchester, New Hampshire 03470
    Holiday Rental House - 4 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
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 12, 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 May 30, 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...
    See all reviews
    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
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 5
    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
    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
    Amenities & Details
    • Wi-Fi
    • Patio
    • Central Heating
    • Outdoor Dining Area
    • Grill
    • Shared Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 9, 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...
    See all reviews
    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
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Keene
    9 Bedrooms, 7 Bathrooms, Sleeps 18 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    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
    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...
    View all property information
    Location Information
    Keene, New Hampshire 03431
    Holiday Rental House - 9 Bedrooms, 7 Bathrooms, Sleeps 18
    Save time - get the best Chesterfield rentals sent straight to your email!
    Get the List
    3 BDR Farmhouse on Tranquil 105 acre Organic Farm1 / 15
    (1)Excellent
    Walpole
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    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 August 20, 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
    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
    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 September 30, 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 July 12, 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
    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...
    View all property information
    Location Information
    Winchester, New Hampshire 03470
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Stay at a Craft Brewery1 / 17
    (1)Excellent
    Winchester
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 15, 2019
    The place is the Outlaw Brewing Co. It is a few miles outside of Winchester. Received a warm welcome from the owners Rick and Sarah Horton. The suite is part of the main house...
    See all reviews
    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...
    View all property information
    Location Information
    Winchester, New Hampshire 03470
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Westminster, VT
    1 Bedroom, 1 Bathroom, Sleeps 12 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is an exclusive Tentrr site. Tentrr partners with farmers, ranchers, and other property owners to offer unique outdoor accommodations on beautiful private land. Each Tentrr Signature site includes a 10'x12' safari-style canvas tent on a raised platform, and you'll find a queen-size single or...
    View all property information
    Location Information
    Westminster, Vermont 05158
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 12
    Troy
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    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...
    View all property information
    Location Information
    Troy, New Hampshire 03447
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
    Winchester
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Inquire today for Winter and Summer Getaways!! 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...
    View all property information
    Location Information
    Winchester, New Hampshire 03470
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
    Northfield, MA
    Studio, 1 Bathroom, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • 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 &...
    View all property information
    Location Information
    Northfield, Massachusetts 01360
    Condo/Apartment - 1 Bathroom, Sleeps 4
    List your property
    Owner log in