West Chesterfield Holiday Rentals

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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for West Chesterfield holiday rentals

Outdoor pool, a heated pool

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.2 out of 10, Wonderful, (20 reviews)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
The price is HK$304
HK$2,259 total
includes taxes & fees
2 Mar - 3 Mar
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (47 reviews)
"Very cute apartment, clean and nice furnishings, bed was very comfortable."
United States
Matthew H.
The price is HK$907
HK$1,580 total
includes taxes & fees
17 Feb - 18 Feb
Lovely 2nd Floor Apartment
Interior

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"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 HK$664
HK$1,616 total
includes taxes & fees
28 Feb - 1 Mar
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Beach

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, (49 reviews)
"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.
The price is HK$703
HK$2,304 total
includes taxes & fees
16 Feb - 17 Feb
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Lobby

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Dover
8.6 out of 10, Excellent, (33 reviews)
"Very nice accommodations and location!"
United States
Michael M.
The price is HK$1,000
HK$3,002 total
includes taxes & fees
1 Mar - 2 Mar
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59 reviews)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
United States
Louis T.
The price is HK$1,367
HK$2,467 total
includes taxes & fees
9 Mar - 10 Mar
Family Friendly Hilltop House In Putney Vermont
Outdoor spa tub

Modern Downtown 12ppl Hot Tub Fire Pit Games

Modern Downtown 12ppl Hot Tub Fire Pit Games
Keene
9.6 out of 10, Exceptional, (22 reviews)
"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.
The price is HK$1,129
HK$2,344 total
includes taxes & fees
8 Feb - 9 Feb
Modern Downtown 12ppl Hot Tub Fire Pit Games
Smart TV, fireplace, Netflix, streaming services

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.8 out of 10, Exceptional, (22 reviews)
"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.
The price is HK$658
HK$3,163 total
includes taxes & fees
3 Mar - 4 Mar
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Private kitchen

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, (2 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.
The price is HK$977
HK$2,039 total
includes taxes & fees
19 Feb - 20 Feb
The Studio with a View. Bring your dog, too!
1 bedroom, WiFi, bed sheets

Unique and charming guesthouse in Brattleboro, Vermont

Unique and charming guesthouse in Brattleboro, Vermont
Brattleboro
The price is HK$875
HK$1,439 total
includes taxes & fees
9 Feb - 10 Feb
Unique and charming guesthouse in Brattleboro, Vermont
Living area

Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
10.0 out of 10, Exceptional, (1 review)
"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 HK$1,078
HK$3,238 total
includes taxes & fees
11 Feb - 12 Feb
Stunning Glass House nestled in the Vermont wilderness!
TV, books

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
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is HK$1,599
HK$1,972 total
includes taxes & fees
8 Feb - 9 Feb
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Terrace/patio

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is HK$1,367
HK$1,699 total
includes taxes & fees
10 Feb - 11 Feb
Vikings Villages Resort - Double Bed Room
Interior

Stratton Woods · Secluded Vermont Cabin Retreat

Stratton Woods · Secluded Vermont Cabin Retreat
Wardsboro
10.0 out of 10, Exceptional, (1 review)
"Cabin was wonderful!Thank you,The Katz Family "
United States
kim k.
The price is HK$1,016
HK$3,246 total
includes taxes & fees
3 Mar - 4 Mar
Stratton Woods · Secluded Vermont Cabin Retreat
Terrace/patio

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, (16 reviews)
"We had an awesome time here. The property was well stocked with essentials, affordable us some opportunity to unwind, explore the creek, and hang out with the fire pit, board games, and the kids enjoyed the ridge racer arcade. Would absolutely come back!"
United States
Joseph R.
The price is HK$1,563
HK$3,549 total
includes taxes & fees
2 Mar - 3 Mar
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Fridge, microwave, oven, stovetop

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, (2 reviews)
"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 HK$1,648
HK$3,933 total
includes taxes & fees
18 Feb - 19 Feb
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
9.8 out of 10, Exceptional, (10 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is HK$1,266
HK$3,813 total
includes taxes & fees
2 Mar - 3 Mar
Chalet Mount Snow/Stratton Skiing/hiking
Property grounds

Lake Whitingham & Mount Snow Area Village Apartment

Lake Whitingham & Mount Snow Area Village Apartment
Whitingham
10.0 out of 10, Exceptional, (1 review)
"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 HK$1,094
HK$2,389 total
includes taxes & fees
16 Feb - 17 Feb
Lake Whitingham & Mount Snow Area Village Apartment
Interior

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Wardsboro
10.0 out of 10, Exceptional, (5 reviews)
"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.
The price is HK$1,953
HK$4,432 total
includes taxes & fees
2 Mar - 3 Mar
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
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
"Friendly staff and a really good value. I've stayed here twice and it was a nice, clean room, and the place is well located. "
Catherine 1-night trip
Posted 3 days ago
The Putney Inn

Find out more about West Chesterfield

Search for holiday rentals in West Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in West Chesterfield using one of the methods below:

  • View our selection of featured holiday rentals in West Chesterfield
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Look no further and take a look at our great range of rental properties in West Chesterfield!

Frequently asked questions

Can I find a holiday rental in West Chesterfield?

Yes, there are holiday rentals close to the most popular sights in West Chesterfield, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the riverfront in West Chesterfield. Make sure you have time to check out the entertainment choices and theatres during your trip.

What are some of the best holiday rentals that West Chesterfield has to offer?

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms: This holiday home rental outside of West Chesterfield is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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, Wantastiquet Mountain and Connecticut River are other places worth a visit.

What’s a holiday rental in West Chesterfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in West Chesterfield. Holiday rentals provide amenities like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a small group gathering.