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West Chesterfield Holiday Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for West Chesterfield holiday rentals

Terrace/patio

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, (17 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is HK$706
HK$1,235 total
includes taxes & fees
24 Aug - 25 Aug
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Property grounds

2. Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (63 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is HK$1,370
HK$2,510 total
includes taxes & fees
1 Sept - 2 Sept
Family Friendly Hilltop House In Putney Vermont
Property grounds

3. Yurt Oasis in the woods of Hinsdale, NH

Yurt Oasis in the woods of Hinsdale, NH
Hinsdale
9.4 out of 10, Exceptional, (6 reviews)
"It was a very pleasant & peaceful night! They were very pleasant, helpful & very detailed when giving all the information/instructions on how to check in & how to use the incinerator toilet! Places to eat ,hike etc…."
United States
Julie
The price is HK$579
HK$1,054 total
includes taxes & fees
24 Aug - 25 Aug
Yurt Oasis in the woods of Hinsdale, NH
Exterior

4. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (14 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is HK$1,040
HK$3,620 total
includes taxes & fees
1 Sept - 2 Sept
Chalet Mount Snow/Stratton Skiing/hiking
Outdoor dining

5. 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$432
HK$639 total
includes taxes & fees
16 Aug - 17 Aug
2 private mountain RV pads for rent. Full hook ups
Interior

6. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (61 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is HK$911
HK$1,605 total
includes taxes & fees
27 Aug - 28 Aug
Lovely 2nd Floor Apartment
Private kitchen

7. 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, (4 reviews)
"What a great get away spot. Such a charming little cabin. The fireflies in the evening were a delight. Clean and cozy."
United States
s p.
The price is HK$981
HK$2,057 total
includes taxes & fees
7 Sept - 8 Sept
The Studio with a View. Bring your dog, too!
Living area

8. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.0 out of 10, Wonderful, (2 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.
Stunning Glass House nestled in the Vermont wilderness!
Outdoor pool, a heated pool

9. 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$534
HK$2,492 total
includes taxes & fees
31 Aug - 1 Sept
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
3 bedrooms

10. Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls

Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls
Walpole
10.0 out of 10, Exceptional, (6 reviews)
"A cozy little cottage on a beautiful property. Great for 4 adults or a small family "
United States
Sheilah Z.
The price is HK$2,306
HK$2,860 total
includes taxes & fees
16 Aug - 17 Aug
Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls
Beach

11. 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)
"Fire place was awesome! Great place to stay! Had everything in the kitchen we needed. All the beds were comfy! "
United States
Susan S.
The price is HK$636
HK$2,243 total
includes taxes & fees
20 Aug - 21 Aug
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Terrace/patio

12. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is HK$2,158
HK$2,678 total
includes taxes & fees
25 Aug - 26 Aug
Vikings Villages Resort - Double Bed Room
TV, books

13. 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
9.6 out of 10, Exceptional, (9 reviews)
"This was a very cute rental in a beautiful part of New Hampshire, but it was much smaller than we imagined."
United States
Kelly
The price is HK$2,306
HK$2,740 total
includes taxes & fees
16 Aug - 17 Aug
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Lobby

14. 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, (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.
The price is HK$824
HK$2,830 total
includes taxes & fees
18 Aug - 19 Aug
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Property grounds

15. Large Farmhouse with expansive views, firepit 15 min north of Keene

Large Farmhouse with expansive views, firepit 15 min north of Keene
Walpole
The price is HK$3,078
HK$3,816 total
includes taxes & fees
16 Aug - 17 Aug
Large Farmhouse with expansive views, firepit 15 min north of Keene
Smart TV, fireplace, Netflix, streaming services

16. 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
9.6 out of 10, Exceptional, (27 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is HK$1,212
HK$3,826 total
includes taxes & fees
14 Sept - 15 Sept
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Exterior detail

17. 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, (9 reviews)
"We had a great"
United States
Meredith B.
The price is HK$946
HK$2,214 total
includes taxes & fees
27 Aug - 28 Aug
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Coffee/tea maker, fridge, microwave, oven

18. 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, (4 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.
The price is HK$1,726
HK$4,078 total
includes taxes & fees
14 Sept - 15 Sept
Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!
Terrace/patio

19. Cozy Studio | Ski-In Access + Kitchenette

Cozy Studio | Ski-In Access + Kitchenette
West Dover
10.0 out of 10, Exceptional, (3 reviews)
"Fabulous! Clean, accommodating staff, great amenities, beautiful view, super easy access to skiing! Would def stay here again. "
United States
Kathy S.
The price is HK$1,365
HK$1,742 total
includes taxes & fees
24 Aug - 25 Aug
Cozy Studio | Ski-In Access + Kitchenette
Terrace/patio

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, (19 reviews)
"Cute place, very pet-friendly."
United States
Jeff H.
The price is HK$1,609
HK$3,698 total
includes taxes & fees
31 Aug - 1 Sept
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

Hampton Inn Brattleboro

Hampton Inn Brattleboro

10/10 Excellent
"Too tired to think about it. Sorry."
Jacquelyn 1-night trip
Posted 7 hours ago
Hampton Inn Brattleboro

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?

Family Friendly Hilltop House In Putney Vermont: This holiday home rental outside of West Chesterfield is located on a lake, and has a balcony, a selection of games and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.