A stone archway surrounded by lush greenery and trees.

West Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for West Chesterfield vacation rentals

A yurt interior with a bed, wooden lattice walls, and a door leading to an outdoor balcony.

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, (21 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
$138 nightly
The price is $150
Nov 30 - Dec 1
Total with taxes and fees
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
A compact kitchen with wooden cabinets, a built-in microwave, and a refrigerator.

2. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"super cute tiny house! my partner and I had a wonderful time here. It's super close to downtown Brattleboro in a beautiful neighborhood"
United States
Anthony L.
$84 nightly
The price is $95
Nov 30 - Dec 1
Total with taxes and fees
Cozy Vermont Tiny Home Get Away
A garden with a wooden pergola, purple flowers, and a river view.

3. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (65 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.
$232 nightly
The price is $259
Nov 5 - Nov 6
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
A modern, compact cabin with large windows, a wooden exterior, and a small porch with outdoor seating.

4. 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.
$243 nightly
The price is $272
Nov 9 - Nov 10
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
A yurt with a deck, two Adirondack chairs, and a stone fire pit in a forest setting.

5. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.6 out of 10, Exceptional, (13 reviews)
"Enjoyed my stay"
United States
Ian C.
$135 nightly
The price is $146
Nov 9 - Nov 10
Total with taxes and fees
Yurt Oasis in the woods of Hinsdale, NH
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

6. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.4 out of 10, Exceptional, (3 reviews)
"The glass part of the house is stunning! We wanted to spend all of our time there, and wished that we could enjoy the view from the kitchen and bedroom too. We opted to sleep on the fold-out bed in the glass room instead of in the below-ground bedroom. It was a nice experience!"
United States
Chris O.
$379 nightly
The price is $425
Nov 18 - Nov 19
Total with taxes and fees
Stunning Glass House nestled in the Vermont wilderness!
A rustic wooden cabin with a thatched roof, a wooden deck, and two Adirondack chairs.

7. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
$320 nightly
The price is $323
Nov 5 - Nov 6
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
A wooden interior with a kitchen, bar area, and dining space.

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

The Studio with a View. Bring your dog, too!
Brattleboro
9.8 out of 10, Exceptional, (8 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.
$225 nightly
The price is $252
Nov 18 - Nov 19
Total with taxes and fees
The Studio with a View. Bring your dog, too!
A wooden house with a porch lit by string lights, surrounded by snow.

9. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (17 reviews)
"Clean, cozy, set back and had all the amenities that you would need"
United States
Chelsea G.
$342 nightly
The price is $387
Nov 5 - Nov 6
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
A deck with two wicker chairs and a string of lights against a backdrop of trees and a sunset.

10. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.8 out of 10, Exceptional, (6 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
$112 nightly
The price is $127
Nov 9 - Nov 10
Total with taxes and fees
The Eagles Wing at The CHM - Private Apartment
A modern kitchen with granite countertops, stainless steel appliances, and a central island.

11. Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Keene
9.8 out of 10, Exceptional, (6 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.
$422 nightly
The price is $458
Nov 9 - Nov 10
Total with taxes and fees
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
A modern kitchen with a wooden countertop, dark cabinets, and a large window.

12. Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (27 reviews)
"Great stay, clean, accommodating and great location. Will stay again!"
United States
cody s.
$330 nightly
The price is $358
Nov 9 - Nov 10
Total with taxes and fees
Modern Downtown Escape HotTub Fire Pit Games 12ppl
A spacious cabin with a wooden interior, a dining area, a sofa, and a fireplace.

13. Cozy Cedar Cabin 8 Min to Mount Snow

Cozy Cedar Cabin 8 Min to Mount Snow
Dover
$543 nightly
The price is $613
Nov 10 - Nov 11
Total with taxes and fees
Cozy Cedar Cabin 8 Min to Mount Snow
Property grounds

14. 3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails

3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
Halifax
10.0 out of 10, Exceptional, (2 reviews)
"This place was honestly amazing. All secluded and even with how far away the cabin was from the main road the cabin had everything you could imagine and everything felt perfect. 10/10 would return"
United States
Justin M.
$425 nightly
The price is $476
Nov 9 - Nov 10
Total with taxes and fees
3-bedroom cabin in tranquil Halifax with cozy charm, direct VAST access, trails
A cozy living room with a large flat-screen TV, a wooden cabinet, a round coffee table, and a potted plant.

15. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (73 reviews)
"Easy parking. Works for a short trip. Convenient to get to."
United States
heather
$213 nightly
The price is $238
Nov 5 - Nov 6
Total with taxes and fees
Lovely 2nd Floor Apartment
A room with a wood-burning stove, a brick fireplace, a mounted television, and a sign above the fireplace.

16. Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"The place was absolutely relaxing, clean, and one of the best host we’ve ever had an experience with. Will come back!!"
United States
Scott S.
$239 nightly
The price is $270
Nov 10 - Nov 11
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
A spacious living area with a high ceiling, wooden beams, a dining table with chairs, a kitchen with modern appliances, and a cozy seating area with a sofa and armchairs.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
$593 nightly
The price is $616
Nov 8 - Nov 9
Total with taxes and fees
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A spacious living area with a high ceiling, wooden beams, a fireplace, and a large wooden coffee table.

18. Seasons ski-in/ski-out condo with balcony and wood-burning fireplace

Seasons ski-in/ski-out condo with balcony and wood-burning fireplace
Dover
8.6 out of 10, Excellent, (37 reviews)
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."
United States
Evan C.
$325 nightly
The price is $367
Nov 5 - Nov 6
Total with taxes and fees
Seasons ski-in/ski-out condo with balcony and wood-burning fireplace
A blue house with a porch, a wooden bench, and a door.

19. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.4 out of 10, Exceptional, (11 reviews)
"Very satisfied with the stay . Clean quiet and relaxing stay."
United States
JAMES S.
$202 nightly
The price is $226
Nov 9 - Nov 10
Total with taxes and fees
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A wooden deck with a black Adirondack chair and a small table, surrounded by trees.

20. Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Wardsboro
10.0 out of 10, Exceptional, (20 reviews)
"Cute place, very pet-friendly."
United States
Jeff H.
$372 nightly
The price is $420
Nov 9 - Nov 10
Total with taxes and fees
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
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 West Chesterfield Hotel Reviews

The Putney Inn

The Putney Inn

10/10 Excellent
"Quiet, clean, safe area. Good breakfast- fruit, yogurt, waffles plus all the usual cereal, toast etc."
Martha 1-night trip
Posted less than an hour ago
The Putney Inn

Find out more about West Chesterfield

Everything you need to know about West 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 West 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 West Chesterfield vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

West Chesterfield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in West 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 West 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 $226 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 West Chesterfield rentals

At Expedia, we put the best West 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 West 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 West 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 West 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 West Chesterfield?

Yes, you can find vacation rentals close to popular sights in West Chesterfield, or you can select a more secluded option if you'd like a relaxing place to stay. Nature enthusiasts will enjoy the riverfront in West Chesterfield. Make sure you have time to check out the entertainment choices and theaters during your trip.

What's the top vacation rental that West Chesterfield has to offer?

Amazing lake views & access,HotTub & sauna, quality game Rm. 230-10 star Reviews: Visitors like this West Chesterfield vacation home rental. It 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’s there to see and do in West Chesterfield?

Madame Sherri Forest and Madame Sherris Castle Ruins are a couple of scenic spots to enjoy the outdoors, whereas Actors Theatre Playhouse is one of the cultural attractions. While here, Connecticut River and United States Navy Seabee Bridge are other places worth a visit.

What’s a vacation rental in West Chesterfield like?

Vacation rentals are private properties you can stay in for several days or longer in West Chesterfield. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for families.