Chesterfield Vacation Rentals

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Check prices for these dates

Tonight
Dec 1 - Dec 2
Tomorrow
Dec 2 - Dec 3
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Vacation Rentals in Chesterfield

Interior
Lovely 2nd Floor Apartment

Vacation Home in Greenfield

10.0 out of 10, Exceptional, (44)
"Our stay was so amazing. The hosts were wonderul and really adapatable to our family needs."
United States
Wendy M.
The price is ￥18,132
￥31,595 total
includes taxes & fees
Dec 3 - Dec 4
Lovely 2nd Floor Apartment
Sauna
Wellness Getaway with a Personal Sauna, and Private River Beach!

Cabin in Newfane

2.0 star property
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
The price is ￥21,084
￥39,707 total
includes taxes & fees
Dec 7 - Dec 8
Wellness Getaway with a Personal Sauna, and Private River Beach!
Exterior
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Cabin in Fitzwilliam

10.0 out of 10, Exceptional, (13)
"Loved the area"
United States
Jose R.
The price is ￥19,538
￥32,552 total
includes taxes & fees
Dec 2 - Dec 3
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Exterior
Tiny house on the Ashuelot river family and pet friendly

Cottage in Swanzey

The price is ￥9,371
￥13,557 total
includes taxes & fees
Dec 14 - Dec 15
Tiny house on the Ashuelot river family and pet friendly
Exterior
Mountain Chalet mins from Mt Snow Skiing/hiking

Chalet in East Dover

9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is ￥18,292
￥68,102 total
includes taxes & fees
Dec 2 - Dec 3
Mountain Chalet mins from Mt Snow Skiing/hiking
Property grounds
Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Apartment in Dover

10.0 out of 10, Exceptional, (4)
"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"
United States
Erica H.
The price is ￥13,275
￥32,120 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Outdoor spa tub
Hot Tub, Game Room, Fire Pit, Dog friendly, 8 minutes to Ski Mount Snow

Chalet in West Dover

10.0 out of 10, Exceptional, (20)
"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.
The price is ￥18,132
￥82,787 total
includes taxes & fees
Dec 2 - Dec 3
Hot Tub, Game Room, Fire Pit, Dog friendly, 8 minutes to Ski Mount Snow
Property grounds
Lake Whitingham & Mount Snow Area Village Apartment

Apartment in Whitingham

2.0 star property
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.
The price is ￥21,865
￥47,753 total
includes taxes & fees
Dec 2 - Dec 3
Lake Whitingham & Mount Snow Area Village Apartment
Fridge, microwave, oven, stovetop
Downtown Hot Tub Escape

Vacation Home in Keene

9.6 out of 10, Exceptional, (21)
"Nice house in a nice location. "
United States
Rob B.
The price is ￥19,780
￥43,661 total
includes taxes & fees
Dec 3 - Dec 4
Downtown Hot Tub Escape
Interior
Stunning Glass House nestled in the Vermont wilderness!

Vacation Home in 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.
The price is ￥26,651
￥70,956 total
includes taxes & fees
Dec 16 - Dec 17
Stunning Glass House nestled in the Vermont wilderness!
TV, books
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Cottage in Walpole

10.0 out of 10, Exceptional, (8)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is ￥31,962
￥39,085 total
includes taxes & fees
Dec 2 - Dec 3
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Property grounds
Family Friendly Hilltop House In Putney Vermont

Vacation Home in Putney

9.4 out of 10, Exceptional, (57)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
The price is ￥23,115
￥44,256 total
includes taxes & fees
Dec 3 - Dec 4
Family Friendly Hilltop House In Putney Vermont
Exterior
Vikings Villages Resort - Double Bed Room

Chalet in Guilford

The price is ￥42,950
￥57,439 total
includes taxes & fees
Dec 2 - Dec 3
Vikings Villages Resort - Double Bed Room
Fridge, microwave, oven, stovetop
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

Vacation Home in 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.
The price is ￥31,705
￥79,415 total
includes taxes & fees
Dec 2 - Dec 3
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Dining
Couples 2 Bedroom Retreat-Close to Shelburne Falls

Vacation Home in Colrain

10.0 out of 10, Exceptional, (4)
"This place was great! Even though it was raining we enjoyed the hot tub! It was super clean and comfortable. "
United States
KayKay S.
The price is ￥26,551
￥58,095 total
includes taxes & fees
Dec 2 - Dec 3
Couples 2 Bedroom Retreat-Close to Shelburne Falls
Property grounds
Owl's Nest Treehouse

Cabin in Alstead

10.0 out of 10, Exceptional, (13)
"Great place . Would highly recommend it.!"
United States
Peter G.
The price is ￥42,950
￥53,380 total
includes taxes & fees
Dec 3 - Dec 4
Owl's Nest Treehouse
Outdoor dining
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Vacation Home in Walpole

10.0 out of 10, Exceptional, (50)
"Worked out perfectly for us!"
United States
Andrew P.
The price is ￥39,357
￥86,422 total
includes taxes & fees
Dec 2 - Dec 3
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Exterior
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST

Cabin in West Dover

10.0 out of 10, Exceptional, (2)
"It was a sweet and cozy little cottage. Absolutely perfect. Clean, safe and so close to the mountain!! Would absolutely love to stay here again!"
United States
Susanne G.
The price is ￥38,264
￥94,534 total
includes taxes & fees
Dec 7 - Dec 8
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
Outdoor dining
Charming Home Walk to Downtown!

Vacation Home in 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.
The price is ￥38,264
￥100,997 total
includes taxes & fees
Dec 2 - Dec 3
Charming Home Walk to Downtown!
Dining
FaLL Western Mass Getaway-Airhockey-Firepit

Vacation Home in Colrain

9.8 out of 10, Exceptional, (38)
"Great place and convenient to get to and from Berkshire East."
United States
Jeffrey B.
The price is ￥42,950
￥98,392 total
includes taxes & fees
Dec 2 - Dec 3
FaLL Western Mass Getaway-Airhockey-Firepit
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 Covered Bridge Inn

The Covered Bridge Inn

10/10 Excellent
"Room very nice, comfortable clean "
Harlan 1-night trip
Posted 2 days ago
The Covered Bridge Inn

Find out more about Chesterfield

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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?

Beautiful Custom Built Timber Frame Home, Sleeps 11: This vacation home rental outside of Chesterfield is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 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 garden, a selection of games, and a hot tub 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.