Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Chesterfield vacation rentals

Private kitchen

Cabin in Brattleboro

The Studio with a View. Bring your dog, too!
2.0 star property
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.
$233 nightly
The price is $261
Jan 21 - Jan 22
Total with taxes and fees
The Studio with a View. Bring your dog, too!
Exterior

Cabin in Newfane

Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"The folks are SUPER and made me feel very welome"
United States
Mark
$228 nightly
The price is $255
Jan 25 - Jan 26
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
Interior

Vacation Home in Greenfield

Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (47 reviews)
"Close to downtown, clean & comfortable!"
United States
Robbi C.
$180 nightly
The price is $201
Jan 23 - Jan 24
Total with taxes and fees
Lovely 2nd Floor Apartment
Exterior detail

Cabin in Fitzwilliam

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
10.0 out of 10, Exceptional, (13 reviews)
"Loved the area"
United States
Jose R.
$192 nightly
The price is $208
Jan 21 - Jan 22
Total with taxes and fees
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Property grounds

Apartment in Whitingham

Lake Whitingham & Mount Snow Area Village Apartment
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
$273 nightly
The price is $306
Jan 21 - Jan 22
Total with taxes and fees
Lake Whitingham & Mount Snow Area Village Apartment
Outdoor spa tub

Vacation Home in Keene

Modern Downtown 12ppl Hot Tub Fire Pit Games
9.6 out of 10, Exceptional, (21 reviews)
"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."
United States
Jack P.
$256 nightly
The price is $277
Jan 22 - Jan 23
Total with taxes and fees
Modern Downtown 12ppl Hot Tub Fire Pit Games
Terrace/patio

Chalet in Guilford

Vikings Villages Resort - Double Bed Room
$213 nightly
The price is $216
Jan 21 - Jan 22
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
Exterior

Chalet in East Dover

Chalet Mount Snow/Stratton Skiing/hiking
9.8 out of 10, Exceptional, (10 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
$433 nightly
The price is $489
Jan 25 - Jan 26
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
TV, books

Cottage in Walpole

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
$231 nightly
The price is $250
Jan 21 - Jan 22
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Exterior

Chalet in West Dover

8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
10.0 out of 10, Exceptional, (21 reviews)
"Whole hearted recommend this property for anyone looking to stay in the area. Great location, great atmosphere and most importantly great house. 10/10 hidden gem. "
United States
Joshua L.
$598 nightly
The price is $676
Jan 26 - Jan 27
Total with taxes and fees
8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
Living area

Vacation Home in Guilford

Stunning Glass House nestled in the Vermont wilderness!
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.
$412 nightly
The price is $462
Feb 18 - Feb 19
Total with taxes and fees
Stunning Glass House nestled in the Vermont wilderness!
Exterior

Cabin in Alstead

Owl's Nest Treehouse
10.0 out of 10, Exceptional, (16 reviews)
"10/10 across the board! The cabin was a great experience. The hot tub was amazing. They have their own store near by with lots of goodies. They were very helpful with any questions we had. Would come here again!"
United States
Adriana
$309 nightly
The price is $335
Jan 21 - Jan 22
Total with taxes and fees
Owl's Nest Treehouse
Property grounds

Vacation Home in Putney

Family Friendly Hilltop House In Putney Vermont
9.4 out of 10, Exceptional, (59 reviews)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
$273 nightly
The price is $305
Jan 28 - Jan 29
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
Fridge, microwave, oven, stovetop

Vacation Home in Keene

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
10.0 out of 10, Exceptional, (2 reviews)
"Thanks to Bill and Angela. We had a wonderful few days staying in your clean, quiet, and very comfortable home. We often choose VRBOs for our travels, whether in the U.S. or abroad—Freiburg, Paris, Bangkok—and this has truly been one of the best experiences.The highlight: this home is the most well-equipped place we’ve ever stayed in—everything we could possibly need was provided, and more. Complete in every way!On top of that, the location is perfect—close to shopping, hiking, fishing, and even...
United States
Xilin J.
$557 nightly
The price is $604
Jan 21 - Jan 22
Total with taxes and fees
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Exterior

Vacation Home in Whitingham

14mi to Mt. Snow! Arcade, Private Suite, King Bed!
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.
$448 nightly
The price is $502
Jan 21 - Jan 22
Total with taxes and fees
14mi to Mt. Snow! Arcade, Private Suite, King Bed!
TV, books, stereo

Vacation Home in Dover

Secluded Vermont Chalet w/ Sweeping Mountain Views
2.0 star property
$472 nightly
The price is $533
Jan 27 - Jan 28
Total with taxes and fees
Secluded Vermont Chalet w/ Sweeping Mountain Views
Terrace/patio

Vacation Home in Walpole

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
10.0 out of 10, Exceptional, (50 reviews)
"We had a very lovely stay. "
United States
mary c.
$537 nightly
The price is $583
Jan 21 - Jan 22
Total with taxes and fees
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Property grounds

Cabin in West Dover

A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
9.4 out of 10, Exceptional, (3 reviews)
"Clean, comfortable, our 2nd time staying here - very nice."
United States
Dan G.
$637 nightly
The price is $697
Jan 21 - Jan 22
Total with taxes and fees
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
Living area

Apartment in Whitingham

Free HOT Breakfast for each guest everyday! Located in charming Whitingham
2.0 star property
$519 nightly
The price is $581
Jan 21 - Jan 22
Total with taxes and fees
Free HOT Breakfast for each guest everyday! Located in charming Whitingham
TV, offices

Vacation Home in Keene

Modern 6BR Home for Large Groups & Families
2.0 star property
$837 nightly
The price is $908
Feb 17 - Feb 18
Total with taxes and fees
Modern 6BR Home for Large Groups & Families
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

Farm Road Estate

Farm Road Estate

10/10 Excellent
"Amazing stay Beautiful room Great fireplace Close to mount snow Great service "
Alessandra Mac Carthy 1-night trip
Posted 14 hours ago
Farm Road Estate

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 $201 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.

Explore a world of travel with Expedia

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.