Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for Chesterfield vacation rentals

House (2 Bedrooms) | Interior

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 ￥24,564
￥65,845 total
includes taxes & fees
Jun 15 - Jun 16
Hiking Trails On-site: Cozy Falls Brook Cabin
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (55 reviews)
"We really enjoyed your place. It was clean and quiet, with some nice design touches. Beautiful woodwork coming up the stairs!! We used it for a self-crafted meditation retreat."
United States
E Kelly S.
The price is ￥18,640
￥32,479 total
includes taxes & fees
Jun 16 - Jun 17
Lovely 2nd Floor Apartment
Fridge, microwave, stovetop, coffee/tea maker

Hiking Trails On-Site: Cozy Falls Brook Cabin

Hiking Trails On-Site: Cozy Falls Brook Cabin
Dummerston
10.0 out of 10, Exceptional, (17 reviews)
"We had a great stay! Cabin is cozy and met all of our needs for the weekend. We loved exploring the nearby trails and shops. Our dogs loved it as well :) "
United States
Kelsey M.
The price is ￥21,995
￥68,388 total
includes taxes & fees
Jun 15 - Jun 16
Hiking Trails On-Site: Cozy Falls Brook Cabin
Property grounds

John's Mountain Hideaway

John's Mountain Hideaway
Jaffrey
10.0 out of 10, Exceptional, (1 review)
"Everything we needed"
United States
Lori S.
The price is ￥40,138
￥78,564 total
includes taxes & fees
Jun 14 - Jun 15
John's Mountain Hideaway
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (60 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is ￥27,021
￥48,965 total
includes taxes & fees
Jun 15 - Jun 16
Family Friendly Hilltop House In Putney Vermont
Fridge, microwave, oven, stovetop

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.2 out of 10, Wonderful, (26 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is ￥29,341
￥56,048 total
includes taxes & fees
Jun 15 - Jun 16
Modern Downtown Escape HotTub Fire Pit Games 12ppl
TV, books

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
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is ￥41,377
￥50,644 total
includes taxes & fees
Jun 14 - Jun 15
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Fridge, microwave, oven, stovetop

Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
9.8 out of 10, Exceptional, (50 reviews)
"Our 4th week here and our crew could not be happier with the accommodations"
United States
Maureen A.
The price is ￥47,041
￥105,807 total
includes taxes & fees
Jun 16 - Jun 17
Spacious 5BR w/ Hot Tub & Games
Private kitchen

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, (2 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 ￥25,206
￥48,190 total
includes taxes & fees
Jun 23 - Jun 24
The Studio with a View. Bring your dog, too!
Terrace/patio

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Wilmington
9.8 out of 10, Exceptional, (46 reviews)
"Great location. Incredible outdoor space and comfortable furnishings."
United States
Debby B.
The price is ￥21,032
￥72,772 total
includes taxes & fees
Jun 29 - Jun 30
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
House (3 Bedrooms) | Interior

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 ￥23,601
￥69,709 total
includes taxes & fees
Jun 29 - Jun 30
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Living area

Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
10.0 out of 10, Exceptional, (1 review)
"The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love."
United States
Grant D.
The price is ￥36,760
￥84,687 total
includes taxes & fees
Jul 7 - Jul 8
Stunning Glass House nestled in the Vermont wilderness!
Exterior

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (14 reviews)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
The price is ￥34,839
￥85,053 total
includes taxes & fees
Jun 16 - Jun 17
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Living area

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
8.8 out of 10, Excellent, (3 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 ￥58,440
￥102,855 total
includes taxes & fees
Jun 12 - Jun 13
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Outdoor dining

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester
Townshend
The price is ￥33,234
￥57,721 total
includes taxes & fees
Jun 15 - Jun 16
Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester
Property grounds

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 ￥35,321
￥101,437 total
includes taxes & fees
Jun 22 - Jun 23
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
Terrace/patio

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is ￥44,151
￥54,434 total
includes taxes & fees
Jun 14 - Jun 15
Vikings Villages Resort - Double Bed Room
Fridge, microwave, oven, stovetop

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 ￥30,826
￥77,519 total
includes taxes & fees
Jun 15 - Jun 16
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Property grounds

Father's Day Special-Game Room, Barrel Sauna, Fire Pit, Hot Tub, Dogs Welcome!

Father's Day Special-Game Room, Barrel Sauna, Fire Pit, Hot Tub, Dogs Welcome!
Dover
10.0 out of 10, Exceptional, (9 reviews)
"We had a great family ski trip and stay in this cozy house. Good location close to town and was the perfect setup up to accommodate our two families of four. Beth and Jason were very responsive and easy to communicate with, would highly recommend! "
United States
James D.
The price is ￥30,066
￥90,568 total
includes taxes & fees
Jun 16 - Jun 17
Father's Day Special-Game Room, Barrel Sauna, Fire Pit, Hot Tub, Dogs Welcome!
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (11 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is ￥15,044
￥65,942 total
includes taxes & fees
Jun 14 - Jun 15
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

8/10 Good
"The room and common areas were clean and well maintained. The front desk staff were very friendly and helpful when we arrived, which made check-in a pleasant experience. The breakfast was good overall; however, breakfast service ended at 9:00 a.m., and by 8:30 a.m. several items had already run out and were not replenished. Since we arrived late the night before, the early breakfast ending time was a bit challenging for our group. One thing to consider when booking is room location. We stayed on the first floor and could hear quite a bit of noise from the room above us. If noise is a concern, I would recommend requesting a room on the second floor. Overall, we had a positive stay and appreciated the cleanliness and friendly service."
Christina 1-night trip
Posted 3 hours 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:

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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 Spofford Lake. While here, Asbury United Methodist Church and Chesterfield Town Hall 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.