West Chesterfield Holiday Rentals

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Our top choices for West Chesterfield holiday rentals

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 AU$309
includes taxes & fees
20 May - 21 May
Lovely 2nd Floor Apartment

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is AU$468
includes taxes & fees
6 May - 7 May
Vikings Villages Resort - Double Bed Room

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 AU$365
includes taxes & fees
4 May - 5 May
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

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 AU$360
includes taxes & fees
6 May - 7 May
Wellness Getaway with a Personal Sauna, and Private River Beach!

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, (11 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 AU$221
includes taxes & fees
2 May - 3 May
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

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 AU$380
includes taxes & fees
6 May - 7 May
The Studio with a View. Bring your dog, too!

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 AU$469
includes taxes & fees
6 May - 7 May
Owl's Nest Treehouse

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 AU$285
includes taxes & fees
31 May - 1 June
Cozy apt in beautiful secluded spot 15 mins from Mt Snow

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)
"Perfect spot for Mount Snow "
United States
Bobby
The price is AU$436
includes taxes & fees
3 May - 4 May
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

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 AU$388
includes taxes & fees
3 May - 4 May
Family Friendly Hilltop House In Putney Vermont

Stratton Woods · Secluded Vermont Cabin Retreat

Stratton Woods · Secluded Vermont Cabin Retreat
Wardsboro
9.4 out of 10, Exceptional, (3 reviews)
"Cabin was wonderful!Thank you,The Katz Family "
United States
kim k.
The price is AU$530
includes taxes & fees
3 May - 4 May
Stratton Woods · Secluded Vermont Cabin Retreat

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 AU$724
includes taxes & fees
2 May - 3 May
Outdoor Adventure Hub! Family Home in West Dover

14mi to Mt. Snow! Arcade, Private Suite, King Bed!

14mi to Mt. Snow! Arcade, Private Suite, King Bed!
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 AU$699
includes taxes & fees
4 May - 5 May
14mi to Mt. Snow! Arcade, Private Suite, King Bed!

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)
"Nice house in a nice location. "
United States
Rob B.
The price is AU$411
includes taxes & fees
3 May - 4 May
Modern Downtown Escape HotTub Fire Pit Games 12ppl

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)
"Great place with great amenities! "
United States
Rachel R.
The price is AU$428
includes taxes & fees
6 May - 7 May
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

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 AU$383
includes taxes & fees
3 May - 4 May
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

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)
"The accommodations were comfortable, but a little dated. Everything worked well and it was ery close to Mount Snow!"
United States
Elizabeth S.
The price is AU$407
includes taxes & fees
12 May - 13 May
Cozy 3 bedroom condo 2.5 miles to Mount Snow

Modern Mount Snow Gnarvana - Balcony, Loft, Pets, Hiking

Modern Mount Snow Gnarvana - Balcony, Loft, Pets, Hiking
Dover
10.0 out of 10, Exceptional, (26 reviews)
"Great location, clean. Easy to walk to magic carpet."
United States
Anonymous traveller
The price is AU$529
includes taxes & fees
3 May - 4 May
Modern Mount Snow Gnarvana - Balcony, Loft, Pets, Hiking

2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is AU$106
includes taxes & fees
2 May - 3 May
2 private mountain RV pads for rent. Full hook ups

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 AU$751
includes taxes & fees
2 May - 3 May
Outdoor Adventure Hub! Family Home in West Dover
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

Find out more about West Chesterfield

Everything you need to know about West Chesterfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the West Chesterfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

West Chesterfield holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A West Chesterfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of West Chesterfield holiday rentals we have selected for you start as low as AU$309 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on West Chesterfield rentals

At Expedia, we put the best West Chesterfield holiday 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 holiday.

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. 

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, West River 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.