Chesterfield Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Chesterfield

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.
$309 nightly
The price is $335
Dec 14 - Dec 15
Total with taxes and fees
Owl's Nest Treehouse
Smart TV, fireplace, DVD player, table tennis
Beautiful Custom Built Timber Frame Home, Sleeps 11

Vacation Home in Wilmington

10.0 out of 10, Exceptional, (108)
"Met family here and was a fantastic place for get together "
United States
Melissa C.
Beautiful Custom Built Timber Frame Home, Sleeps 11
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.
$564 nightly
The price is $630
Dec 7 - Dec 8
Total with taxes and fees
FaLL Western Mass Getaway-Airhockey-Firepit
Outdoor dining
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.

Mobile Home in Fitzwilliam

10.0 out of 10, Exceptional, (10)
"This house is amazing. "
United States
Amanda Q.
Secluded waterfront 2-bedroom / 2 bath on private 152 acre Sportsman's Pond.
Interior
Lovely 2nd Floor Apartment

Vacation Home in Greenfield

10.0 out of 10, Exceptional, (45)
"Our stay was so amazing. The hosts were wonderul and really adapatable to our family needs."
United States
Wendy M.
$181 nightly
The price is $202
Dec 7 - Dec 8
Total with taxes and fees
Lovely 2nd Floor Apartment
Terrace/patio
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Vacation Home in Townshend

10.0 out of 10, Exceptional, (6)
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC
Outdoor dining
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Cottage in Wilmington

8.6 out of 10, Excellent, (64)
"Great location and super cute"
United States
Jeff S.
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Fridge, microwave, oven, stovetop
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Vacation Home in Townshend

10.0 out of 10, Exceptional, (62)
"Another great summer vacation with family at this beautiful property! Have already booked for next year."
United States
Shirlee B.
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
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
$227 nightly
The price is $254
Dec 9 - Dec 10
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
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.
$559 nightly
The price is $632
Dec 14 - Dec 15
Total with taxes and fees
Hot Tub, Game Room, Fire Pit, Dog friendly, 8 minutes to Ski Mount Snow
Outdoor dining
Six Bedroom Mountain Estate with Internet Access

Vacation Home in West Dover

10.0 out of 10, Exceptional, (16)
"This house was great for a family gathering! It had a lot of space, has a great game room for the kids, is very clean and comfortable, and is close to Mt. Snow! It checked off all the boxes we were looking for-"
United States
Steven Z.
Six Bedroom Mountain Estate with Internet Access
Exterior
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

Cabin in Townshend

10.0 out of 10, Exceptional, (60)
"THE perfect place to stay for a getaway weekend (or longer!). Courtney was so responsive and helpful. Cannot recommend this place enough. :)"
United States
Patricia Emogene M.
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Smart TV, fireplace, foosball, books
Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking

Vacation Home in Whitingham

10.0 out of 10, Exceptional, (31)
"The house was so well stocked and very child friendly. So many personal touches that made us feel at home and comfortable. Would definitely stay again!"
United States
Brittany M.
Mt Snow for families! Sprawling home, great views, skiing, snowmobiling, hiking
Interior
Private 6 bedroom Chalet 5min to Mt Snow

Chalet in Dover

9.8 out of 10, Exceptional, (14)
"Great stay and successful bachelor party, host was very accommodating with check-in & check-out timing. Several phenomenal golf courses within 10 minutes of the property, gorgeous views! "
United States
Nick B.
Private 6 bedroom Chalet 5min to Mt Snow
Smart TV, fireplace, DVD player, books
This is it! Spacious & secluded cabin on 25 acres with gorgeous mountain views!

Cabin in Halifax

9.8 out of 10, Exceptional, (120)
"Great place to stay with friends and family. Will be visiting again!"
United States
Adam K.
This is it! Spacious & secluded cabin on 25 acres with gorgeous mountain views!
Exterior
Cozy Updated Log Cabin with Mountain Views close to Monadnock

Cabin in Fitzwilliam

9.6 out of 10, Exceptional, (28)
"a fantastic weekend getaway in the mountains! quiet neighborhood with stunning night time views of the stars. such a cozy cabin, very clean, linens provided, nice property with a little fire pit too! very friendly host, easy to contact and pleasant. "
United States
Jennifer
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Exterior
The Jelly Mill-A Peaceful River Retreat

Vacation Home in Guilford

10.0 out of 10, Exceptional, (64)
"Beautiful rural location next to the Green River. A peaceful relaxing place to stay. We would love to stay here again "
United States
Georgene M.
The Jelly Mill-A Peaceful River Retreat
Exterior
Waterfront Cottage on Scenic Sportsman Pond

Cottage in Fitzwilliam

9.6 out of 10, Exceptional, (44)
"Excellent location,plenty of water activities and equipment,fun place, Owners very nice and very helpful."
United States
Cathy M.
Waterfront Cottage on Scenic Sportsman Pond
Game room
Luxury ADA Unit - 101

Apartment in Wilmington

$543 nightly
The price is $552
Dec 5 - Dec 6
Total with taxes and fees
Luxury ADA Unit - 101
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.
$510 nightly
The price is $553
Dec 9 - Dec 10
Total with taxes and fees
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

The White House Inn

The White House Inn

10/10 Excellent
"Retro and sweet. Nice staff. No elevator. "
Christine 2-night trip
Posted 2 days ago
The White House Inn

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 $202 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?

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.