A rural landscape with a grassy field, a dirt path, and a hill covered with autumn-colored trees.

Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Chesterfield vacation rentals

A rustic cabin with a covered porch, a small shed, and outdoor seating.

1. RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (18 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
$148 nightly
The price is $160
Sep 22 - Sep 23
Total with taxes and fees
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

2. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.6 out of 10, Exceptional, (8 reviews)
"Cozy and clean yurt in the woods surrounded by sounds of hooting owls and a super friendly and help host made for the perfect family weekend. Can’t wait to plan another stay. Made roughing it not rough at all. "
United States
Allisha C.
$149 nightly
The price is $162
Sep 22 - Sep 23
Total with taxes and fees
Yurt Oasis in the woods of Hinsdale, NH
A garden with purple flowers and a river in the background.

3. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (63 reviews)
"The house was all we expected. Very comfortable and ready for us when we arrived. It’s a bit out of the way, at the end of a private road, but quiet and secluded. Our host was attentive without being intrusive. She clearly wanted to make sure our stay met our expectations and was pleasant. All in all, a delightful way to visit Vermont!"
United States
Susan G.
$246 nightly
The price is $276
Sep 8 - Sep 9
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
A lakeside park with picnic tables and a concrete walkway.

4. 2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
$75 nightly
The price is $81
Sep 6 - Sep 7
Total with taxes and fees
2 private mountain RV pads for rent. Full hook ups
A wooden interior with a kitchen, bar area, and dining space.

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

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (4 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.
$218 nightly
The price is $244
Sep 13 - Sep 14
Total with taxes and fees
The Studio with a View. Bring your dog, too!
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

6. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (25 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
$329 nightly
The price is $357
Sep 9 - Sep 10
Total with taxes and fees
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

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

Wellness Getaway with a Personal Sauna, and Private River Beach!
Newfane
10.0 out of 10, Exceptional, (3 reviews)
"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "
United States
Joseph P.
$308 nightly
The price is $345
Oct 6 - Oct 7
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

8. 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, (4 reviews)
"Communication with the host was easy and the house was great. I would definitely book this home again if/when I come back to Keene."
United States
Jeremy S.
$442 nightly
The price is $480
Sep 7 - Sep 8
Total with taxes and fees
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

9. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (64 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
$181 nightly
The price is $202
Sep 7 - Sep 8
Total with taxes and fees
Lovely 2nd Floor Apartment
A wooden house with a porch lit by string lights, surrounded by snow.

10. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (16 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
$376 nightly
The price is $425
Sep 13 - Sep 14
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
A spacious living room with a checkered sofa, a grey sofa, and a patterned rug. There is a staircase leading to another level, and a dining area with a table and chairs.

11. 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
9.6 out of 10, Exceptional, (9 reviews)
"This was a very cute rental in a beautiful part of New Hampshire, but it was much smaller than we imagined."
United States
Kelly
$314 nightly
The price is $341
Sep 7 - Sep 8
Total with taxes and fees
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
A rustic wooden cabin with a thatched roof, a wooden deck, and two Adirondack chairs.

12. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
$335 nightly
The price is $340
Sep 7 - Sep 8
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
A four-poster bed with a grey bedspread, a wooden nightstand with a lamp, a wooden dresser, and a chair.

13. Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls

Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls
Walpole
10.0 out of 10, Exceptional, (6 reviews)
"A cozy little cottage on a beautiful property. Great for 4 adults or a small family "
United States
Sheilah Z.
$314 nightly
The price is $341
Sep 7 - Sep 8
Total with taxes and fees
Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls
A room with a wooden bed, a mirror, and a window.

14. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
$660 nightly
The price is $691
Sep 9 - Sep 10
Total with taxes and fees
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Two Adirondack chairs and a fire pit in a grassy field with a forested hill in the background.

15. Large Farmhouse with expansive views, firepit 15 min north of Keene

Large Farmhouse with expansive views, firepit 15 min north of Keene
Walpole
$420 nightly
The price is $455
Sep 7 - Sep 8
Total with taxes and fees
Large Farmhouse with expansive views, firepit 15 min north of Keene
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a built-in oven, and a large island with bar stools.

16. 2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.

2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
Fitzwilliam
$273 nightly
The price is $296
Sep 6 - Sep 7
Total with taxes and fees
2 Bedroom waterfront home on a peaceful pond, large deck and dock. Enjoy nature.
An aerial view of a house surrounded by a forest with autumn foliage.

17. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (15 reviews)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
United States
Jonathan
$515 nightly
The price is $577
Sep 22 - Sep 23
Total with taxes and fees
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

18. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (55 reviews)
"This is the second time we have stayed at this property. It is very spacious, cozy, and clean. The beds are very comfortable. It had everything we needed "
United States
Staci M.
$588 nightly
The price is $656
Sep 8 - Sep 9
Total with taxes and fees
Spacious 5BR w/ Hot Tub & Games
A wooden deck leading to a dark-colored house with a white door and windows.

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

A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
West Dover
9.0 out of 10, Wonderful, (4 reviews)
"Clean, comfortable, our 2nd time staying here - very nice."
United States
Dan G.
$646 nightly
The price is $707
Sep 20 - Sep 21
Total with taxes and fees
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
A wooden barrel structure with a staircase and railing, surrounded by a forest.

20. Mt Snow Summer Spcls--Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!

Mt Snow Summer Spcls--Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!
Dover
10.0 out of 10, Exceptional, (11 reviews)
"Awesome place, fantastic amenities and easy to get to. Looking forward to coming back."
United States
Connor S.
$792 nightly
The price is $805
Sep 27 - Sep 28
Total with taxes and fees
Mt Snow Summer Spcls--Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!
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

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"All around great stay. Thank you."
Christina 3-night trip
Posted 16 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

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 $160 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.

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?

5 Bdrm Lakehouse, sleeps 18, private dock, hot tub, 15 minutes to Mount Snow: 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 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 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 Cheshire Children's Museum, or get out into nature at a spot like Spofford Lake. While here, Pisgah State Park and Asbury United Methodist Church 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.