West Chesterfield Holiday Rentals

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Check prices for these dates

In two weeks
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul

Our top choices for West Chesterfield holiday rentals

Interior

Holiday Home in Greenfield

Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (49 reviews)
"This is a comfortable and spacious apartment in a great location central to everything in Greenfield. David is also an excellent host who communicated clearly throughout our visit. Would definitely stay here again. "
United States
Geoffrey B.
The price is HK$910
HK$1,577 total
includes taxes & fees
22 Mar - 23 Mar
Lovely 2nd Floor Apartment
Exterior detail

Apartment in Greenfield

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
9.6 out of 10, Exceptional, (8 reviews)
"We had an amazing stay! The property was spotless and comfortable. We felt right at home and can’t wait to stay here again! "
United States
Garth P.
The price is HK$592
HK$1,712 total
includes taxes & fees
23 Mar - 24 Mar
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Exterior

Cabin in Newfane

Wellness Getaway with a Personal Sauna, and Private River Beach!
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.
The price is HK$1,058
HK$2,010 total
includes taxes & fees
22 Mar - 23 Mar
Wellness Getaway with a Personal Sauna, and Private River Beach!
Terrace/patio

Camping in Hinsdale

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
10.0 out of 10, Exceptional, (10 reviews)
"Yert was perfect and stocked with everything we needed,property owner showed up to make sure we had everything we needed then left us in complete privacy,location was amazing with a great scenic view."
United States
Jerry S.
The price is HK$705
HK$1,233 total
includes taxes & fees
20 Mar - 21 Mar
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Terrace/patio

Chalet in Guilford

Vikings Villages Resort - Double Bed Room
The price is HK$1,763
HK$2,194 total
includes taxes & fees
22 Mar - 23 Mar
Vikings Villages Resort - Double Bed Room
Outdoor pool, a heated pool

Apartment in Dover

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
9.4 out of 10, Exceptional, (23 reviews)
"Perfect spot for Mount Snow "
United States
Bobby
The price is HK$482
HK$2,493 total
includes taxes & fees
23 Mar - 24 Mar
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior

Cabin in Alstead

Owl's Nest Treehouse
10.0 out of 10, Exceptional, (19 reviews)
"We loved our stay at The Owls Nest! The location was very private, and everything was exceptionally clean. Perfect for a quick weekend getaway to relax. Would highly recommend for a couple looking to enjoy a quiet weekend. "
United States
Samantha R.
The price is HK$2,155
HK$2,627 total
includes taxes & fees
25 Mar - 26 Mar
Owl's Nest Treehouse
Property grounds

Holiday Home in Putney

Family Friendly Hilltop House In Putney Vermont
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is HK$1,230
HK$2,326 total
includes taxes & fees
23 Mar - 24 Mar
Family Friendly Hilltop House In Putney Vermont
Outdoor spa tub

Holiday Home in Keene

Modern Downtown 12ppl Hot Tub Fire Pit Games
9.6 out of 10, Exceptional, (22 reviews)
"Nice house in a nice location. "
United States
Rob B.
The price is HK$1,132
HK$2,351 total
includes taxes & fees
22 Mar - 23 Mar
Modern Downtown 12ppl Hot Tub Fire Pit Games
Interior

Apartment in Dover

Cozy apt in beautiful secluded spot 15 mins from Mt Snow
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$666
HK$1,620 total
includes taxes & fees
31 Mar - 1 Apr
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Private kitchen

Cabin in Brattleboro

The Studio with a View. Bring your dog, too!
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$1,042
HK$2,089 total
includes taxes & fees
1 Apr - 2 Apr
The Studio with a View. Bring your dog, too!
TV, books

Cottage in Walpole

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful cozy cottage. Very clean. Wonderful host."
United States
Gloria A.
The price is HK$1,615
HK$1,990 total
includes taxes & fees
22 Mar - 23 Mar
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Property grounds

Apartment in Whitingham

Lake Whitingham & Mount Snow Area Village Apartment
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$1,097
HK$2,405 total
includes taxes & fees
20 Mar - 21 Mar
Lake Whitingham & Mount Snow Area Village Apartment
Beach

Condo in West Dover

Cozy 3 bedroom condo 2.5 miles to Mount Snow
9.2 out of 10, Wonderful, (51 reviews)
"Lovely condo set against the trees in the heart of Mt. Snow apres. It have everything needed for a family of 4 - 6. "
United States
Alan S.
The price is HK$705
HK$2,240 total
includes taxes & fees
25 Mar - 26 Mar
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Interior

Holiday Home in Dover

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
9.8 out of 10, Exceptional, (15 reviews)
"We enjoyed our stay."
United States
Anonymous traveller
The price is HK$1,756
HK$4,490 total
includes taxes & fees
22 Mar - 23 Mar
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Terrace/patio

Holiday Home in Walpole

Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
10.0 out of 10, Exceptional, (51 reviews)
"We had a very lovely stay. "
United States
mary c.
The price is HK$2,511
HK$4,969 total
includes taxes & fees
23 Mar - 24 Mar
Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9
Exterior

Chalet in East Dover

Chalet Mount Snow/Stratton Skiing/hiking
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$946
HK$3,351 total
includes taxes & fees
7 Apr - 8 Apr
Chalet Mount Snow/Stratton Skiing/hiking
Living area

Holiday Home in Guilford

Stunning Glass House nestled in the Vermont wilderness!
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$952
HK$3,076 total
includes taxes & fees
24 Mar - 25 Mar
Stunning Glass House nestled in the Vermont wilderness!
Fridge, microwave, oven, stovetop

Holiday Home in Colrain

Colrain Spring into Adventure HotTub AirHockey Firepit
9.8 out of 10, Exceptional, (48 reviews)
"Great house for family gatherings "
United Kingdom
John Paul B.
The price is HK$2,220
HK$4,991 total
includes taxes & fees
22 Mar - 23 Mar
Colrain Spring into Adventure HotTub AirHockey Firepit
Smart TV, fireplace, Netflix, streaming services

Chalet in Dover

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
9.8 out of 10, Exceptional, (25 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$897
HK$3,493 total
includes taxes & fees
23 Mar - 24 Mar
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
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

Big Bears Lodge

Big Bears Lodge

10/10 Excellent
"Place is great and location as well, 5 minutes from Mount Snow."
Matheus 2-night trip
Posted 1 day ago
Big Bears Lodge

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:

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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 12 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, Connecticut River and United States Navy Seabee Bridge 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.