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

Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

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, (21 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is AED 380
AED 600 total
includes taxes & fees
9 Nov - 10 Nov
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A compact kitchen with wooden cabinets, a built-in microwave, and a refrigerator.

2. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"super cute tiny house! my partner and I had a wonderful time here. It's super close to downtown Brattleboro in a beautiful neighborhood"
United States
Anthony L.
The price is AED 268
AED 352 total
includes taxes & fees
30 Nov - 1 Dec
Cozy Vermont Tiny Home Get Away
A garden with a wooden pergola, purple flowers, and a river view.

3. 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 AED 539
AED 982 total
includes taxes & fees
11 Nov - 12 Nov
Family Friendly Hilltop House In Putney Vermont
A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

4. 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 AED 340
AED 537 total
includes taxes & fees
9 Nov - 10 Nov
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.

5. 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 AED 606
AED 991 total
includes taxes & fees
16 Nov - 17 Nov
Wellness Getaway with a Personal Sauna, and Private River Beach!
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 AED 757
AED 1,316 total
includes taxes & fees
9 Nov - 10 Nov
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A cozy cabin with a stone fire pit, surrounded by lush greenery and tall trees.

7. 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
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A rustic wooden cabin with a thatched roof, a wooden deck, and two Adirondack chairs.

8. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
Vikings Villages Resort - Double Bed Room
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

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

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
9.8 out of 10, Exceptional, (6 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 AED 705
AED 1,682 total
includes taxes & fees
9 Nov - 10 Nov
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

10. 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.
Stunning Glass House nestled in the Vermont wilderness!
A wooden house with a porch lit by string lights, surrounded by snow.

11. 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.
Chalet Mount Snow/Stratton Skiing/hiking
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, (49 reviews)
"Great property and location. Communications with host excellent. Love the privacy and availability of firewood."
United States
Rod M.
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A cozy living room with a large flat-screen TV, a wooden cabinet, a round coffee table, and a potted plant.

13. 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 AED 562
AED 874 total
includes taxes & fees
8 Nov - 9 Nov
Lovely 2nd Floor Apartment
Property grounds

14. 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 AED 681
AED 1,791 total
includes taxes & fees
9 Nov - 10 Nov
3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
A wooden interior with a kitchen, bar area, and dining space.

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

The Studio with a View. Bring your dog, too!
Brattleboro
9.8 out of 10, Exceptional, (8 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 AED 426
AED 877 total
includes taxes & fees
18 Nov - 19 Nov
The Studio with a View. Bring your dog, too!
A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

16. 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 AED 367
AED 452 total
includes taxes & fees
9 Nov - 10 Nov
The Eagles Wing at The CHM - Private Apartment
A lake surrounded by trees, with a wooden deck leading to a white railing.

17. "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 AED 876
AED 1,034 total
includes taxes & fees
8 Nov - 9 Nov
"Pondlife" - Waterfront home in a peaceful, wooded setting.
A cozy living room with a fireplace, leather sofas, and a television mounted on the wall.

18. Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Whitingham
8.4 out of 10, Very good, (7 reviews)
"This apartment is very efficient and really wowed everyone based on the automotive inspired design. It was an impeccable space, well stocked, and the beds were even extremely comfortable. We enjoyed the bar/grill within walking distance, too. Would stay here again. "
United States
Ben B.
The price is AED 1,337
AED 2,250 total
includes taxes & fees
8 Nov - 9 Nov
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
A spacious cabin with a wooden interior, a dining area, a sofa, and a fireplace.

19. Cozy Cedar Cabin 8 Min to Mount Snow

Cozy Cedar Cabin 8 Min to Mount Snow
Dover
The price is AED 639
AED 2,299 total
includes taxes & fees
15 Nov - 16 Nov
Cozy Cedar Cabin 8 Min to Mount Snow
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.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
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.
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Top Chesterfield Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

8/10 Good
"Overall a nice stay. What was disappointing was breakfast ends at 9am. Very disappointed when we came down to eat at 9:15 and it was roped off and over."
Michael 1-night trip
Posted 6 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

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.