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
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Chesterfield vacation rentals

Terrace/patio

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
$173 nightly
The price is $188
Jul 19 - Jul 20
Total with taxes and fees
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (59 reviews)
"Beautiful, thoughtful space on a gorgeous piece of property. "
United States
Jodi W.
$181 nightly
The price is $202
Jul 27 - Jul 28
Total with taxes and fees
Lovely 2nd Floor Apartment
Coffee/tea maker, fridge, microwave, stovetop

Hiking Trails On-Site: Cozy Falls Brook Cabin

Hiking Trails On-Site: Cozy Falls Brook Cabin
Dummerston
10.0 out of 10, Exceptional, (18 reviews)
"So cozy, perfect Vermont vacation!"
United States
Evan S.
$385 nightly
The price is $431
Aug 5 - Aug 6
Total with taxes and fees
Hiking Trails On-Site: Cozy Falls Brook Cabin
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (12 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
$364 nightly
The price is $412
Jul 19 - Jul 20
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
Outdoor dining

2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
$75 nightly
The price is $81
Jul 18 - Jul 19
Total with taxes and fees
2 private mountain RV pads for rent. Full hook ups
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
$377 nightly
The price is $411
Aug 5 - Aug 6
Total with taxes and fees
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.
$487 nightly
The price is $528
Jul 20 - Jul 21
Total with taxes and fees
John's Mountain Hideaway
Fridge, microwave, oven, stovetop

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.
$341 nightly
The price is $370
Jul 21 - Jul 22
Total with taxes and fees
Modern Downtown Escape HotTub Fire Pit Games 12ppl
Terrace/patio

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
$336 nightly
The price is $341
Jul 19 - Jul 20
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
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.
$629 nightly
The price is $689
Jul 20 - Jul 21
Total with taxes and fees
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (61 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
$292 nightly
The price is $327
Jul 20 - Jul 21
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
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, (3 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.
$286 nightly
The price is $320
Jul 27 - Jul 28
Total with taxes and fees
The Studio with a View. Bring your dog, too!
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.
$398 nightly
The price is $446
Jul 22 - Jul 23
Total with taxes and fees
Stunning Glass House nestled in the Vermont wilderness!
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
9.6 out of 10, Exceptional, (9 reviews)
"Easy hand's off check in and great communication with the host. The cottage itself was lovely - my friends and I were in town for a wedding and it was the perfect accommodations! Would definitely stay here again! "
United States
Frances D.
$314 nightly
The price is $341
Jul 20 - Jul 21
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
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.
$456 nightly
The price is $495
Aug 10 - Aug 11
Total with taxes and fees
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Coffee/tea maker, fridge, microwave, oven

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.
$596 nightly
The price is $666
Aug 9 - Aug 10
Total with taxes and fees
Spacious 5BR w/ Hot Tub & Games
Property grounds

Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.6 out of 10, Exceptional, (5 reviews)
"This place can only be described with one word, "WOW". That is the exact thing I said when pulling up to it. The driveway is steep and dirt so it can be intimidating but it isn't that bad at all. We went here on our honeymoon and had to ride 3 hours to get there on a motorcycle. This place was equipped with a beautiful outdoor firepit, 2 gas propane grills, and an indoor propane heater (leave the door cracked). The showers are located at the house on the property and were very clean. There's a...
United States
Ian
$143 nightly
The price is $155
Jul 26 - Jul 27
Total with taxes and fees
Yurt Oasis in the woods of Hinsdale, NH
Property grounds

Dover Summer Specials-Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!

Dover Summer Specials-Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!
Dover
10.0 out of 10, Exceptional, (10 reviews)
"Awesome place, fantastic amenities and easy to get to. Looking forward to coming back."
United States
Connor S.
$779 nightly
The price is $792
Aug 4 - Aug 5
Total with taxes and fees
Dover Summer Specials-Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!
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
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.
$535 nightly
The price is $599
Jul 18 - Jul 19
Total with taxes and fees
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"Clean, comfortable and fairly priced."
Cynthia 1-night trip
Posted 10 hours ago
Hampton Inn Brattleboro

Find out more about Chesterfield

Everything you need to know about Chesterfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterfield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chesterfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $188 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.