West Chesterfield Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for West Chesterfield holiday rentals

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$987
HK$2,043 total
includes taxes & fees
20 May - 21 May
The Studio with a View. Bring your dog, too!
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (53 reviews)
"Very clean, cozy and lots of nice plants! "
United States
Mary
The price is HK$909
HK$1,575 total
includes taxes & fees
20 May - 21 May
Lovely 2nd Floor Apartment
Exterior

Owl's Nest Treehouse

Owl's Nest Treehouse
Alstead
10.0 out of 10, Exceptional, (21 reviews)
"Great time easy to get to clean quiet and peaceful definitely would recommend for romantic getaway "
United States
Garrett B.
The price is HK$2,153
HK$2,659 total
includes taxes & fees
17 May - 18 May
Owl's Nest Treehouse
Terrace/patio

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is HK$1,558
HK$1,913 total
includes taxes & fees
19 May - 20 May
Vikings Villages Resort - Double Bed Room
Exterior

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.
The price is HK$1,253
HK$2,245 total
includes taxes & fees
28 May - 29 May
Wellness Getaway with a Personal Sauna, and Private River Beach!
Terrace/patio

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, (12 reviews)
"Stacy and her husband were very communicative and accommodating. We had everything we needed in the yurt and they provided us with some extra supplies as well. Would definitely stay again!"
United States
Gina M.
The price is HK$705
HK$1,232 total
includes taxes & fees
15 May - 16 May
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
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
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is HK$533
HK$2,539 total
includes taxes & fees
21 May - 22 May
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior detail

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
9.6 out of 10, Exceptional, (8 reviews)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is HK$958
HK$2,207 total
includes taxes & fees
27 May - 28 May
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
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 host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is HK$1,374
HK$2,504 total
includes taxes & fees
27 May - 28 May
Family Friendly Hilltop House In Putney Vermont
Interior

Outdoor Adventure Hub! Family Home in West Dover

Outdoor Adventure Hub! Family Home in West Dover
3.0 star property
West Dover
The price is HK$1,198
HK$4,083 total
includes taxes & fees
21 May - 22 May
Outdoor Adventure Hub! Family Home in West Dover
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$2,018
HK$2,402 total
includes taxes & fees
17 May - 18 May
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Fridge, microwave, oven, stovetop

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.2 out of 10, Wonderful, (23 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is HK$1,397
HK$2,697 total
includes taxes & fees
20 May - 21 May
Modern Downtown Escape HotTub Fire Pit Games 12ppl
Terrace/patio

Charming 1BR Retreat | Ski-In Access

Charming 1BR Retreat | Ski-In Access
West Dover
The price is HK$1,327
HK$1,654 total
includes taxes & fees
18 May - 19 May
Charming 1BR Retreat | Ski-In Access
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, (51 reviews)
"Cozy place, very close to the moover and Mount Snow. Host was very responsive. Would definitely book again!"
United States
dory p.
The price is HK$705
HK$2,282 total
includes taxes & fees
20 May - 21 May
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Exterior

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester

Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester
Townshend
The price is HK$1,761
HK$3,007 total
includes taxes & fees
19 May - 20 May
Vermont Cozy Cabin with Fireplace Near Hiking Trails, Stratton, Manchester
Exterior

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, (14 reviews)
"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "
United States
Jacklyn D.
The price is HK$1,558
HK$3,964 total
includes taxes & fees
19 May - 20 May
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Outdoor dining

2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is HK$431
HK$637 total
includes taxes & fees
15 May - 16 May
2 private mountain RV pads for rent. Full hook ups
4 bedrooms, travel cot, Internet, bed sheets

Outdoor Adventure Hub! Family Home in West Dover

Outdoor Adventure Hub! Family Home in West Dover
West Dover
10.0 out of 10, Exceptional, (5 reviews)
"The house was just as listed. Everything we needed was there for us upon arrival. The host is amazing and was happy to welcome us in their home. We would definitely come back"
United States
Louis
The price is HK$1,073
HK$4,256 total
includes taxes & fees
20 May - 21 May
Outdoor Adventure Hub! Family Home in West Dover
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$665
HK$1,592 total
includes taxes & fees
31 May - 1 Jun
Cozy apt in beautiful secluded spot 15 mins from Mt Snow
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

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

6/10 Okay
"Room was clean. "
Kathleen 1-night trip
Posted 8 hours ago
Comfort Inn & Suites Brattleboro I-91

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?

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included: This holiday home rental outside of West Chesterfield is located on a lake, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

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.