Photo by Shannon Willitts

West Chesterfield Holiday Rentals

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Our top choices for West Chesterfield holiday rentals

10.0 out of 10, Exceptional, (11)
"Beautiful new home, great for big family and friend groups. Comfortable bedding and furniture. Lots of open space and seating "
United States
Gena L.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Cabin in Alstead

Owl's Nest Treehouse
10.0 out of 10, Exceptional, (13)
"Great place . Would highly recommend it.!"
United States
Peter G.
The price is AU$509
includes taxes & fees
14 Dec - 15 Dec
Owl's Nest Treehouse
9.8 out of 10, Exceptional, (48)
"Overall a nice stay, thanks Jen!"
United States
Anonymous traveller
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
9.4 out of 10, Exceptional, (29)
"This place is enormous with nooks and crannies everywhere to get away, shoot pool, play video games, read, swim, sit in the sauna,barbecue, or wade in the brook below! Some of the rooms are great for a couple, others are better for a bunch of kids who are willing to sleep in a bunk or twin bed. "
United States
khs
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
8.0 out of 10, Very good, (2)
"Place was amazing! Beautiful property and so unique. Being pet friendly was a huge plus! We had a wonderful time!"
United States
Alexia R.
The price is AU$1,830
includes taxes & fees
5 Jan - 6 Jan 2026
Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
9.6 out of 10, Exceptional, (9)
"I really enjoyed every aspect of my stay here and highly recommend the property. "
United States
Gregory G.
Cozy 2-bedroom cabin near Mount Snow 3 min drive
10.0 out of 10, Exceptional, (8)
"Nice in all respects,"
United States
Ken
The price is AU$2,103
includes taxes & fees
13 Dec - 14 Dec
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Holiday Home in Greenfield

Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (45)
"Our stay was so amazing. The hosts were wonderul and really adapatable to our family needs."
United States
Wendy M.
The price is AU$304
includes taxes & fees
14 Dec - 15 Dec
Lovely 2nd Floor Apartment
8.2 out of 10, Very good, (10)
"Lovely place for a large group of people."
United States
Nicole M.
Dog-friendly home w/ WiFi, private washer/dryer, and wood & electric fireplaces
10.0 out of 10, Exceptional, (5)
"We enjoyed our stay."
United States
Anonymous traveller
The price is AU$953
includes taxes & fees
15 Dec - 16 Dec
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
10.0 out of 10, Exceptional, (14)
"Perfect weekend getaway "
United States
Seth G.
The price is AU$660
includes taxes & fees
15 Dec - 16 Dec
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
9.4 out of 10, Exceptional, (16)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
The price is AU$387
includes taxes & fees
14 Dec - 15 Dec
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
10.0 out of 10, Exceptional, (108)
"Met family here and was a fantastic place for get together "
United States
Melissa C.
Beautiful Custom Built Timber Frame Home, Sleeps 11
9.4 out of 10, Exceptional, (42)
"My family and I loved our stay. This cabin had everything we needed and more. One thing we do wish we had was fans in the upstairs rooms, as we stayed in the summer time and it did get quite hot up there. The owners were very helpful, and amazing with communication. We would absolutely love to stay here again one day! "
United States
lizzie m.
Beautiful Lodging at Mount Snow with Hot Tub on Deck
10.0 out of 10, Exceptional, (64)
"Beautiful rural location next to the Green River. A peaceful relaxing place to stay. We would love to stay here again "
United States
Georgene M.
The Jelly Mill-A Peaceful River Retreat
9.8 out of 10, Exceptional, (22)
"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 AU$636
includes taxes & fees
5 Jan - 6 Jan 2026
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Mountain view condo w/ fireplace, shared hot tub, pool, sauna, tennis & shuttle
6.0 out of 10, (1)
"Inside property was great - house was very fun and spacious and clean . HOWEVER..the driveway clearly hadn’t been plowed for a long time when we got there and so once we pulled in our cars were stuck. We were trapped at the house for 3 days. The plow driver came to plow the neighbor and told us he hadn’t been paid by the owners so hadn’t been plowing for some time The owners finally arranged for a different plow to come but not being able to leave for 3 days really affected our ability to...
United States
Allison S.
The Birch. A Spacious Mansion 2 min from Mt. Snow!
9.6 out of 10, Exceptional, (5)
"Property is very clean, beautiful condo and scenery, owner was great and communication was incredible! Highly recommend, great stay!"
United States
Douglas D.
The price is AU$771
includes taxes & fees
15 Dec - 16 Dec
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
10.0 out of 10, Exceptional, (7)
LUX property, Stunning views, private setting,pet friendly, fire pit ,WIFI,AC,EV
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$304 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?

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. : This holiday home rental outside of West Chesterfield is located in the mountains, and has a fireplace, a patio and laundry facilities to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. 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 Sherris Castle Ruins and Wantastiquet Mountain 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.