Chesterfield Vacation Rentals

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Vacation Rentals in Chesterfield

Exterior
Tiny house on the Ashuelot river family and pet friendly

Tiny house on the Ashuelot river family and pet friendly

Swanzey
$80 nightly
The price is $87
Nov 16 - Nov 17
Total with taxes and fees
Tiny house on the Ashuelot river family and pet friendly
Exterior
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Fitzwilliam
10.0 out of 10, Exceptional, (13)
"Our two night stay was great. Loved how close it was to the bike path and the fire pit in the back. Clare was very responsive!"
United States
Camila G.
$190 nightly
The price is $206
Nov 16 - Nov 17
Total with taxes and fees
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Sauna
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, (1)
"The folks are SUPER and made me feel very welome"
United States
Mark
$227 nightly
The price is $254
Nov 18 - Nov 19
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
Exterior
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.
$386 nightly
The price is $436
Nov 16 - Nov 17
Total with taxes and fees
Mountain Chalet mins from Mt Snow Skiing/hiking
Property grounds
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
Nov 14 - Nov 15
Total with taxes and fees
Lake Whitingham & Mount Snow Area Village Apartment
Interior
Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment

Greenfield
10.0 out of 10, Exceptional, (44)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
United States
Shanyn
$180 nightly
The price is $201
Nov 17 - Nov 18
Total with taxes and fees
Lovely 2nd Floor Apartment
Property grounds
Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Dover
10.0 out of 10, Exceptional, (4)
"Catherine contacted me immediately that the studio I had rented was not available but that we could have the adjacent house instead. She moved heaven and earth to make sure we had a king bed ( which is what we wanted). She was very attentive and accommodating. "
United States
Wendy C.
$182 nightly
The price is $206
Nov 30 - Dec 1
Total with taxes and fees
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Interior
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.
$361 nightly
The price is $405
Nov 19 - Nov 20
Total with taxes and fees
Stunning Glass House nestled in the Vermont wilderness!
Property grounds
Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont

Putney
9.4 out of 10, Exceptional, (56)
"Gorgeous property. Super accommodating hosts. Would love to come back in the summer."
United States
Thomas F.
$213 nightly
The price is $238
Nov 23 - Nov 24
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
Outdoor spa tub
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

West Dover
9.6 out of 10, Exceptional, (21)
"great space for adults and teenagers. loved the hot tub! "
United States
Jessica M.
$540 nightly
The price is $610
Nov 16 - Nov 17
Total with taxes and fees
Hot Tub, Game Room, Fire Pit, Dog friendly, 8 minutes to Ski Mount Snow
Fridge, microwave, oven, stovetop
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)
" The home has everything that you could possibly need. The host was great in checking in to make sure our stay was going well and if we needed anything. The beds were comfortable, the living room spacious and a great place to hang out. The house was spotless. The outdoor area is beautiful and a fantastic place to enjoy the beautiful setting. Best VRBO that I have stayed at, we are hoping to make a return trip. Would highly recommend!"
United States
Jeannine H.
$449 nightly
The price is $503
Nov 18 - Nov 19
Total with taxes and fees
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Fridge, microwave, oven, stovetop
Downtown Hot Tub Escape

Downtown Hot Tub Escape

Keene
9.6 out of 10, Exceptional, (21)
"The house was adorable! Great place for a getaway! We did realize almost all of the cups were dirty so we cleaned a lot our first day there. We also had issues with the hot water. As a group of 8 and only one bathroom we made it work but not having hot water was rough! Oh and blowing the fuse anytime we wanted to coffee! But for an old home it was nice!"
United States
Jacqueline V.
$296 nightly
The price is $321
Nov 16 - Nov 17
Total with taxes and fees
Downtown Hot Tub Escape
Exterior
Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room

Guilford
$336 nightly
The price is $368
Nov 16 - Nov 17
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
Property grounds
Owl's Nest Treehouse

Owl's Nest Treehouse

Alstead
10.0 out of 10, Exceptional, (11)
"Great place . Would highly recommend it.!"
United States
Peter G.
$312 nightly
The price is $339
Nov 18 - Nov 19
Total with taxes and fees
Owl's Nest Treehouse
Dining
Couples 2 Bedroom Retreat-Close to Shelburne Falls

Couples 2 Bedroom Retreat-Close to Shelburne Falls

Colrain
10.0 out of 10, Exceptional, (4)
"We had everything we needed for a fun and relaxing family get away. We loved how close it was to great restaurants and activities like rafting, zip lining, and the mountain coaster. The kitchen is fully stocked and everything was clean and well organized.Erica and Casey were great hosts and so helpful in answering any and all of our questions before check in. We will definitely be back! "
United States
Heather B.
$333 nightly
The price is $372
Nov 16 - Nov 17
Total with taxes and fees
Couples 2 Bedroom Retreat-Close to Shelburne Falls
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)
"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.
$231 nightly
The price is $250
Nov 16 - Nov 17
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Exterior
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST

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

West Dover
10.0 out of 10, Exceptional, (2)
"Great place - fast internet, hot tub, x-box - all great for the kids, and close to the ski resorts! Very pleased with everything."
United States
Dan G.
$570 nightly
The price is $624
Nov 30 - Dec 1
Total with taxes and fees
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
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

Walpole
10.0 out of 10, Exceptional, (50)
"A charming updated farmhouse. Lots of sitting and dining areas.... lovely stay."
United States
Mary
$513 nightly
The price is $557
Nov 18 - Nov 19
Total with taxes and fees
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Dining
FaLL Western Mass Getaway-Airhockey-Firepit

FaLL Western Mass Getaway-Airhockey-Firepit

Colrain
9.8 out of 10, Exceptional, (38)
"Couldn’t have been happier with our stay. The space was absolutely perfect for our large family, and the owners couldn’t have been nicer or more helpful. Phenomenal kitchen space (love the island!). Can’t wait to stay here again!"
United States
Taylor C.
$564 nightly
The price is $630
Nov 16 - Nov 17
Total with taxes and fees
FaLL Western Mass Getaway-Airhockey-Firepit
Outdoor dining
Charming Home Walk to Downtown!

Charming Home Walk to Downtown!

Keene
10.0 out of 10, Exceptional, (1)
"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.
$596 nightly
The price is $647
Nov 17 - Nov 18
Total with taxes and fees
Charming Home Walk to Downtown!
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

The Inn At Crumpin Fox

The Inn At Crumpin Fox

10/10 Excellent
"Room was great, we will be back again, favorite place in the valley thus far to stay. "
Christine 2-night trip
Posted 2 days ago
The Inn At Crumpin Fox

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?

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC: This vacation home rental outside of Chesterfield is located in the mountains and has a balcony, a garden, and air-conditioning to put you at ease in your new surroundings. You and your friends and family can relax into your vacation with amenities like a selection of games.

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.