A rural landscape with a grassy field, a dirt path, and a hill covered with autumn-colored trees.

Chesterfield Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Chesterfield vacation rentals

A yurt interior with a bed, wooden lattice walls, and a door leading to an outdoor balcony.

1. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (20 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is ￥15,041
￥25,727 total
includes taxes & fees
Nov 2 - Nov 3
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A garden with a wooden pergola, purple flowers, and a river view.

2. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (65 reviews)
"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"
United States
Susan G.
The price is ￥22,987
￥44,109 total
includes taxes & fees
Nov 4 - Nov 5
Family Friendly Hilltop House In Putney Vermont
A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

3. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.6 out of 10, Exceptional, (13 reviews)
"Enjoyed my stay"
United States
Ian C.
The price is ￥14,048
￥23,795 total
includes taxes & fees
Nov 2 - Nov 3
Yurt Oasis in the woods of Hinsdale, NH
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

4. Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
The price is ￥25,226
￥44,852 total
includes taxes & fees
Nov 4 - Nov 5
Wellness Getaway with a Personal Sauna, and Private River Beach!
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

5. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.4 out of 10, Exceptional, (3 reviews)
"The glass part of the house is stunning! We wanted to spend all of our time there, and wished that we could enjoy the view from the kitchen and bedroom too. We opted to sleep on the fold-out bed in the glass room instead of in the below-ground bedroom. It was a nice experience!"
United States
Chris O.
The price is ￥29,117
￥75,696 total
includes taxes & fees
Nov 8 - Nov 9
Stunning Glass House nestled in the Vermont wilderness!
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

6. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (27 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
The price is ￥32,494
￥59,034 total
includes taxes & fees
Nov 2 - Nov 3
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A rustic wooden cabin with a thatched roof, a wooden deck, and two Adirondack chairs.

7. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is ￥43,357
￥53,808 total
includes taxes & fees
Nov 2 - Nov 3
Vikings Villages Resort - Double Bed Room
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

8. Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
10.0 out of 10, Exceptional, (5 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
The price is ￥30,271
￥72,188 total
includes taxes & fees
Nov 2 - Nov 3
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A grassy field with trees and a red building in the background.

9. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is ￥8,671
￥12,830 total
includes taxes & fees
Oct 31 - Nov 1
2 private mountain RV pads for rent. Full hook ups
A wooden interior with a kitchen, bar area, and dining space.

10. The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (7 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The price is ￥18,162
￥39,236 total
includes taxes & fees
Nov 2 - Nov 3
The Studio with a View. Bring your dog, too!
A cozy living room with a large flat-screen TV, a wooden cabinet, a round coffee table, and a potted plant.

11. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (73 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
The price is ￥24,122
￥39,272 total
includes taxes & fees
Nov 1 - Nov 2
Lovely 2nd Floor Apartment
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

12. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington
9.8 out of 10, Exceptional, (48 reviews)
"Great property and location. Communications with host excellent. Love the privacy and availability of firewood."
United States
Rod M.
The price is ￥16,712
￥66,808 total
includes taxes & fees
Nov 4 - Nov 5
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A wooden house with a porch lit by string lights, surrounded by snow.

13. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (17 reviews)
"Clean, cozy, set back and had all the amenities that you would need"
United States
Chelsea G.
The price is ￥14,773
￥61,726 total
includes taxes & fees
Nov 4 - Nov 5
Chalet Mount Snow/Stratton Skiing/hiking
A lake surrounded by trees, with a wooden deck leading to a white railing.

14. "Pondlife" - Waterfront home in a peaceful, wooded setting.

"Pondlife" - Waterfront home in a peaceful, wooded setting.
Fitzwilliam
10.0 out of 10, Exceptional, (7 reviews)
"Pondlife was clean, calm, cozy, and peaceful...exactly what we wanted...fall foliage was gorgeous....rail trail hiking adjacent to the property and plenty of mountain hiking nearby. If you want to be immersed in nature's beauty, this is perfect..."
United States
Margaret
The price is ￥37,602
￥44,391 total
includes taxes & fees
Oct 31 - Nov 1
"Pondlife" - Waterfront home in a peaceful, wooded setting.
Property grounds

15. 3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails

3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
Halifax
10.0 out of 10, Exceptional, (2 reviews)
"This place was honestly amazing. All secluded and even with how far away the cabin was from the main road the cabin had everything you could imagine and everything felt perfect. 10/10 would return"
United States
Justin M.
The price is ￥29,241
￥78,660 total
includes taxes & fees
Nov 1 - Nov 2
3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

16. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
The price is ￥23,018
￥63,507 total
includes taxes & fees
Nov 4 - Nov 5
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A spacious cabin with a wooden interior, a dining area, a sofa, and a fireplace.

17. Cozy Cedar Cabin 8 Min to Mount Snow

Cozy Cedar Cabin 8 Min to Mount Snow
Dover
The price is ￥25,399
￥89,808 total
includes taxes & fees
Nov 8 - Nov 9
Cozy Cedar Cabin 8 Min to Mount Snow
A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

18. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.8 out of 10, Exceptional, (6 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is ￥24,280
￥31,356 total
includes taxes & fees
Nov 2 - Nov 3
The Eagles Wing at The CHM - Private Apartment
A spacious living area with a high ceiling, wooden beams, a dining table with chairs, a kitchen with modern appliances, and a cozy seating area with a sofa and armchairs.

19. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is ￥32,636
￥100,196 total
includes taxes & fees
Nov 3 - Nov 4
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A wooden deck leading to a dark-colored house with a white door and windows.

20. A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST

A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
West Dover
9.0 out of 10, Wonderful, (4 reviews)
"Clean, comfortable, our 2nd time staying here - very nice."
United States
Dan G.
The price is ￥39,415
￥100,135 total
includes taxes & fees
Nov 4 - Nov 5
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"Great"
Brandie 1-night trip
Posted 2 days ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

  • View our selection of featured holiday rentals in Chesterfield
  • Use the map to find apartments and other holiday homes in the Chesterfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesterfield while they last

Look no further and take a look at our great range of rental properties in Chesterfield!

Frequently asked questions

Can I find a vacation rental in Chesterfield?

Yes, we offer vacation rentals near top sights in Chesterfield, or you can select a more secluded option if you'd like a relaxing place to stay. Chesterfield is known for its shopping and restaurants.

What are some of the best vacation home rentals in Chesterfield?

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: This vacation home rental outside of Chesterfield is located on a river and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

What can I see and do in Chesterfield?

Explore the area and family-friendly sights such as Brattleboro Bowl, or get out into nature at a spot like Spofford Lake. While here, Asbury United Methodist Church and Pisgah State Park are other places worth a visit.

What are vacation rentals like in Chesterfield?

Vacation rentals are private accommodations you can stay in for several days or more in Chesterfield. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for small groups.