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West Chesterfield Vacation Rentals

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Our top choices for West Chesterfield vacation rentals

Interior
Lovely 2nd Floor Apartment

Vacation Home in Greenfield

Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (46)
"Close to downtown, clean & comfortable!"
United States
Robbi C.
$180 nightly
The price is $201
Jan 4 - Jan 5, 2026
Total with taxes and fees
Lovely 2nd Floor Apartment
Property grounds
Lake Whitingham & Mount Snow Area Village Apartment

Apartment in Whitingham

Lake Whitingham & Mount Snow Area Village Apartment
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.
$272 nightly
The price is $305
Jan 2 - Jan 3, 2026
Total with taxes and fees
Lake Whitingham & Mount Snow Area Village Apartment
Exterior
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Apartment in Dover

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
9.2 out of 10, Wonderful, (17)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
$288 nightly
The price is $325
Jan 27 - Jan 28, 2026
Total with taxes and fees
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Cabin in Fitzwilliam

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
10.0 out of 10, Exceptional, (13)
"Loved the area"
United States
Jose R.
$192 nightly
The price is $208
Jan 6 - Jan 7, 2026
Total with taxes and fees
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna
Sauna
Wellness Getaway with a Personal Sauna, and Private River Beach!

Cabin in Newfane

Wellness Getaway with a Personal Sauna, and Private River Beach!
2.0 star property
10.0 out of 10, Exceptional, (2)
"The folks are SUPER and made me feel very welome"
United States
Mark
$228 nightly
The price is $255
Jan 15 - Jan 16, 2026
Total with taxes and fees
Wellness Getaway with a Personal Sauna, and Private River Beach!
Terrace/patio
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Chalet in Dover

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
9.8 out of 10, Exceptional, (22)
"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "
United States
SZU YIN C.
$479 nightly
The price is $541
Jan 4 - Jan 5, 2026
Total with taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Property grounds
Cozy 3 bedroom condo 2.5 miles to Mount Snow

Condo in West Dover

Cozy 3 bedroom condo 2.5 miles to Mount Snow
9.0 out of 10, Wonderful, (46)
"Great quiet location, kitchen had enough essentials for basic cooking to be easy. The king bed was comfortable and the living room is a great hangout spot."
United States
Franklin C.
$261 nightly
The price is $295
Jan 14 - Jan 15, 2026
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Property grounds
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Condo in Dover

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.8 out of 10, Excellent, (32)
"Very nice accommodations and location!"
United States
Michael M.
$403 nightly
The price is $455
Jan 20 - Jan 21, 2026
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
TV, books
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Cottage in Walpole

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
10.0 out of 10, Exceptional, (8)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
$231 nightly
The price is $250
Jan 4 - Jan 5, 2026
Total with taxes and fees
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

Family Friendly Hilltop House In Putney Vermont
9.4 out of 10, Exceptional, (58)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
$254 nightly
The price is $285
Jan 5 - Jan 6, 2026
Total with taxes and fees
Family Friendly Hilltop House In Putney Vermont
Dining
FaLL Western Mass Getaway-Airhockey-Firepit

Vacation Home in Colrain

FaLL Western Mass Getaway-Airhockey-Firepit
9.8 out of 10, Exceptional, (38)
"Great house for family gatherings "
United Kingdom
John Paul B.
$601 nightly
The price is $671
Jan 3 - Jan 4, 2026
Total with taxes and fees
FaLL Western Mass Getaway-Airhockey-Firepit
Fridge, microwave, oven, stovetop
Downtown Hot Tub Escape

Vacation Home in Keene

Downtown Hot Tub Escape
9.6 out of 10, Exceptional, (21)
"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."
United States
Jack P.
$255 nightly
The price is $276
Jan 4 - Jan 5, 2026
Total with taxes and fees
Downtown Hot Tub Escape
Property grounds
Owl's Nest Treehouse

Cabin in Alstead

Owl's Nest Treehouse
10.0 out of 10, Exceptional, (14)
"10/10 across the board! The cabin was a great experience. The hot tub was amazing. They have their own store near by with lots of goodies. They were very helpful with any questions we had. Would come here again!"
United States
Adriana
$311 nightly
The price is $337
Jan 20 - Jan 21, 2026
Total with taxes and fees
Owl's Nest Treehouse
Exterior
Mountain Chalet mins from Mt Snow Skiing/hiking

Chalet in East Dover

Mountain Chalet mins from Mt Snow Skiing/hiking
9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
$370 nightly
The price is $418
Jan 13 - Jan 14, 2026
Total with taxes and fees
Mountain Chalet mins from Mt Snow Skiing/hiking
Outdoor dining
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

Vacation Home in Keene

Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
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.
$553 nightly
The price is $600
Jan 1 - Jan 2, 2026
Total with taxes and fees
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Microwave, oven, stovetop
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

Chalet in Wardsboro

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
10.0 out of 10, Exceptional, (4)
"Impressively clean house! The owners were great to deal with and very responsive. Would certainly recommend to anyone traveling in the area."
United States
Kristen T.
$467 nightly
The price is $528
Jan 14 - Jan 15, 2026
Total with taxes and fees
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Terrace/patio
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Chalet in Wardsboro

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
10.0 out of 10, Exceptional, (14)
"Perfect weekend getaway "
United States
Seth G.
$423 nightly
The price is $478
Jan 20 - Jan 21, 2026
Total with taxes and fees
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Interior
Stunning Glass House nestled in the Vermont wilderness!

Vacation Home in Guilford

Stunning Glass House nestled in the Vermont wilderness!
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.
$396 nightly
The price is $443
Jan 19 - Jan 20, 2026
Total with taxes and fees
Stunning Glass House nestled in the Vermont wilderness!
Outdoor dining
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

Vacation Home in Walpole

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
10.0 out of 10, Exceptional, (50)
"We had a very lovely stay. "
United States
mary c.
$546 nightly
The price is $592
Jan 5 - Jan 6, 2026
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.
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Top West Chesterfield Hotel Reviews

Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

10/10 Excellent
"The room and property in general was amazing. Super comfortable beds, and room plan. Very walkable to many restaurants and attractions in the town center. Easy parking. I wasnt impressed with the "Bistro" that is essentially a starbucks. Also, no free lounge coffee, you have to buy at the Bistro/starbucks. Other than that, it was a really great stay. "
Danielle 1-night trip
Posted 3 days ago
Courtyard by Marriott Keene Downtown

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 $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 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.

Explore a world of travel with Expedia

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?

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns: Visitors like this West Chesterfield vacation home rental. It is located on a river and has an outdoor pool, a fireplace, 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 balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

What’s there to see and do in West Chesterfield?

Madame Sherris Castle Ruins and Wantastiquet Mountain 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.