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
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Chesterfield vacation rentals

Property grounds

1. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.4 out of 10, Exceptional, (6 reviews)
"It was a very pleasant & peaceful night! They were very pleasant, helpful & very detailed when giving all the information/instructions on how to check in & how to use the incinerator toilet! Places to eat ,hike etc…."
United States
Julie
The price is ￥18,433
￥28,888 total
includes taxes & fees
Aug 5 - Aug 6
Yurt Oasis in the woods of Hinsdale, NH
House (2 Bedrooms) | Interior

2. Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
United States
sarah
The price is ￥29,657
￥67,284 total
includes taxes & fees
Aug 5 - Aug 6
Hiking Trails On-site: Cozy Falls Brook Cabin
Property grounds

3. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (62 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is ￥25,878
￥48,196 total
includes taxes & fees
Aug 11 - Aug 12
Family Friendly Hilltop House In Putney Vermont
Coffee/tea maker, fridge, microwave, stovetop

4. Hiking Trails On-Site: Cozy Falls Brook Cabin

Hiking Trails On-Site: Cozy Falls Brook Cabin
Dummerston
10.0 out of 10, Exceptional, (20 reviews)
"So cozy, perfect Vermont vacation!"
United States
Evan S.
The price is ￥22,382
￥70,628 total
includes taxes & fees
Aug 5 - Aug 6
Hiking Trails On-Site: Cozy Falls Brook Cabin
Terrace/patio

5. 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, (15 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is ￥16,958
￥28,177 total
includes taxes & fees
Aug 5 - Aug 6
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Outdoor dining

6. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is ￥8,985
￥13,295 total
includes taxes & fees
Jul 31 - Aug 1
2 private mountain RV pads for rent. Full hook ups
Coffee/tea maker, fridge, microwave, oven

7. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (25 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is ￥36,105
￥64,169 total
includes taxes & fees
Aug 2 - Aug 3
Modern Downtown Escape HotTub Fire Pit Games 12ppl
TV, books

8. Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
9.6 out of 10, Exceptional, (9 reviews)
"This was a very cute rental in a beautiful part of New Hampshire, but it was much smaller than we imagined."
United States
Kelly
The price is ￥45,485
￥53,430 total
includes taxes & fees
Aug 2 - Aug 3
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
3 bedrooms

9. Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls

Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls
Walpole
10.0 out of 10, Exceptional, (6 reviews)
"A cozy little cottage on a beautiful property. Great for 4 adults or a small family "
United States
Sheilah Z.
The price is ￥45,485
￥56,266 total
includes taxes & fees
Aug 3 - Aug 4
Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls
Interior

10. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (60 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is ￥18,967
￥33,231 total
includes taxes & fees
Aug 3 - Aug 4
Lovely 2nd Floor Apartment
Private kitchen

11. 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, (4 reviews)
"What a great get away spot. Such a charming little cabin. The fireflies in the evening were a delight. Clean and cozy."
United States
s p.
The price is ￥18,820
￥40,841 total
includes taxes & fees
Aug 4 - Aug 5
The Studio with a View. Bring your dog, too!
Terrace/patio

12. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is ￥44,927
￥55,574 total
includes taxes & fees
Aug 4 - Aug 5
Vikings Villages Resort - Double Bed Room
Property grounds

13. Large Farmhouse with expansive views, firepit 15 min north of Keene

Large Farmhouse with expansive views, firepit 15 min north of Keene
Walpole
The price is ￥60,702
￥74,902 total
includes taxes & fees
Aug 3 - Aug 4
Large Farmhouse with expansive views, firepit 15 min north of Keene
Coffee/tea maker, fridge, microwave, oven

14. 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, (3 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 ￥32,021
￥79,235 total
includes taxes & fees
Aug 24 - Aug 25
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
House (3 Bedrooms) | Front of property

15. 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 ￥28,590
￥71,019 total
includes taxes & fees
Aug 11 - Aug 12
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Living area

16. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.0 out of 10, Wonderful, (2 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 ￥26,518
￥73,614 total
includes taxes & fees
Aug 12 - Aug 13
Stunning Glass House nestled in the Vermont wilderness!
Living area

17. 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
9.0 out of 10, Wonderful, (4 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 ￥59,467
￥105,394 total
includes taxes & fees
Aug 3 - Aug 4
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Coffee/tea maker, fridge, microwave, oven

18. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (52 reviews)
"Our 4th week here and our crew could not be happier with the accommodations"
United States
Maureen A.
The price is ￥56,248
￥117,940 total
includes taxes & fees
Aug 2 - Aug 3
Spacious 5BR w/ Hot Tub & Games
Property grounds

19. 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 ￥43,293
￥112,524 total
includes taxes & fees
Aug 1 - Aug 2
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
Exterior

20. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (13 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is ￥27,830
￥82,910 total
includes taxes & fees
Aug 13 - Aug 14
Chalet Mount Snow/Stratton Skiing/hiking
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

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

10/10 Excellent
"Room was modern and clean. Actually this is the first clean hotel I found in Keene so far, and I checked few ..."
Dominik 1-night trip
Posted 13 hours ago
Courtyard by Marriott Keene Downtown

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:

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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?

Lovely 2nd Floor Apartment: This vacation home rental outside of Chesterfield offers a garden, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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 Pierces Island State Park. 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.