Chesterfield Vacation Rentals

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Our top choices for Chesterfield vacation rentals

Exterior
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Fitzwilliam
10.0 out of 10, Exceptional, (13)
"Loved the area"
United States
Jose R.
$192 nightly
The price is $208
Jan 6 - Jan 7
Total with taxes and fees
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Property grounds
Lake Whitingham & Mount Snow Area Village Apartment

Lake Whitingham & Mount Snow Area Village Apartment

Lake Whitingham & Mount Snow Area Village Apartment
2.0 star property
Whitingham
10.0 out of 10, Exceptional, (1)
"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.
$272 nightly
The price is $305
Jan 2 - Jan 3
Total with taxes and fees
Lake Whitingham & Mount Snow Area Village Apartment
Sauna
Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!

Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
Newfane
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
$228 nightly
The price is $255
Jan 15 - Jan 16
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
Interior
Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (46)
"Close to downtown, clean & comfortable!"
United States
Robbi C.
$180 nightly
The price is $201
Jan 4 - Jan 5
Total with taxes and fees
Lovely 2nd Floor Apartment
Exterior
Mountain Chalet mins from Mt Snow Skiing/hiking

Mountain Chalet mins from Mt Snow Skiing/hiking

Mountain Chalet mins from Mt Snow Skiing/hiking
East Dover
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
$368 nightly
The price is $416
Jan 13 - Jan 14
Total with taxes and fees
Mountain Chalet mins from Mt Snow Skiing/hiking
Fridge, microwave, oven, stovetop
Downtown Hot Tub Escape

Downtown Hot Tub Escape

Downtown Hot Tub Escape
Keene
9.6 out of 10, Exceptional, (21)
"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.
$255 nightly
The price is $276
Jan 4 - Jan 5
Total with taxes and fees
Downtown Hot Tub Escape
Property grounds
Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (58)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
$254 nightly
The price is $285
Jan 5 - Jan 6
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
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

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Walpole
10.0 out of 10, Exceptional, (8)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
$231 nightly
The price is $250
Jan 4 - Jan 5
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Interior
Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
10.0 out of 10, Exceptional, (1)
"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.
$396 nightly
The price is $443
Jan 19 - Jan 20
Total with taxes and fees
Stunning Glass House nestled in the Vermont wilderness!
Property grounds
Owl's Nest Treehouse

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (14)
"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
$311 nightly
The price is $337
Jan 20 - Jan 21
Total with taxes and fees
Owl's Nest Treehouse
Property grounds
The Studio with a View. Bring your dog, too!

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

The Studio with a View. Bring your dog, too!
2.0 star property
Brattleboro
$241 nightly
The price is $270
Jan 4 - Jan 5
Total with taxes and fees
The Studio with a View. Bring your dog, too!
Dining
FaLL Western Mass Getaway-Airhockey-Firepit

FaLL Western Mass Getaway-Airhockey-Firepit

FaLL Western Mass Getaway-Airhockey-Firepit
Colrain
9.8 out of 10, Exceptional, (38)
"Great house for family gatherings "
United Kingdom
John Paul B.
$601 nightly
The price is $671
Jan 3 - Jan 4
Total with taxes and fees
FaLL Western Mass Getaway-Airhockey-Firepit
Exterior
Secluded Vermont Chalet w/ Sweeping Mountain Views

Secluded Vermont Chalet w/ Sweeping Mountain Views

Secluded Vermont Chalet w/ Sweeping Mountain Views
2.0 star property
Dover
$453 nightly
The price is $512
Jan 5 - Jan 6
Total with taxes and fees
Secluded Vermont Chalet w/ Sweeping Mountain Views
Exterior
Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
$423 nightly
The price is $428
Jan 4 - Jan 5
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
Outdoor dining
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

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, (2)
"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.
$553 nightly
The price is $600
Jan 5 - Jan 6
Total with taxes and fees
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Outdoor dining
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Walpole
10.0 out of 10, Exceptional, (50)
"We had a very lovely stay. "
United States
mary c.
$546 nightly
The price is $592
Jan 5 - Jan 6
Total with taxes and fees
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Outdoor spa tub
8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly

8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly

8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
West Dover
10.0 out of 10, Exceptional, (21)
"Had a delightful time here for the Holiday. Quiet place which held us all comfortably! Easy to get to the places we wanted to go to and was well maintained. Communication with the hosts was fantastic."
United States
Jeannine A.
$725 nightly
The price is $819
Jan 13 - Jan 14
Total with taxes and fees
8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
Fridge, microwave, oven, stovetop
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Whitingham
10.0 out of 10, Exceptional, (14)
"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.
$635 nightly
The price is $711
Jan 21 - Jan 22
Total with taxes and fees
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Exterior
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST

A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST

A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
West Dover
9.4 out of 10, Exceptional, (3)
"Clean, comfortable, our 2nd time staying here - very nice."
United States
Dan G.
$643 nightly
The price is $704
Jan 13 - Jan 14
Total with taxes and fees
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
Game room
Luxury ADA Unit - 101

Luxury ADA Unit - 101

Luxury ADA Unit - 101
Wilmington
$535 nightly
The price is $543
Jan 4 - Jan 5
Total with taxes and fees
Luxury ADA Unit - 101
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

Colonial Motel And Spa

Colonial Motel And Spa

10/10 Excellent
"Great location and service "
Paul 2-night trip
Posted 3 days ago
Colonial Motel And Spa

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 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.