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West Chesterfield Vacation Rentals

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Vacation Rentals in West Chesterfield

Property grounds
Owl's Nest Treehouse

Cabin in Alstead

10.0 out of 10, Exceptional, (12)
"Great place . Would highly recommend it.!"
United States
Peter G.
$310 nightly
The price is $336
Nov 30 - Dec 1
Total with taxes and fees
Owl's Nest Treehouse
Terrace/patio
Outdoor Enthusiasts Paradise in Beautiful Vermont!

Vacation Home in Wilmington

10.0 out of 10, Exceptional, (17)
"Great place. "
United States
Desiree T.
Outdoor Enthusiasts Paradise in Beautiful Vermont!
Fridge, microwave, oven, stovetop
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

Vacation Home in Dover

9.8 out of 10, Exceptional, (47)
"Overall a nice stay, thanks Jen!"
United States
Anonymous traveler
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
Smart TV, fireplace, DVD player, table tennis
Beautiful Custom Built Timber Frame Home, Sleeps 11

Vacation Home in Wilmington

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
Fridge, microwave, oven, stovetop
Cozy 2-bedroom cabin near Mount Snow 3 min drive

Cabin in Dover

2.0 star property
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
Fridge, microwave, oven, stovetop
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Vacation Home in Dover

10.0 out of 10, Exceptional, (7)
"Nice in all respects,"
United States
Ken
$926 nightly
The price is $1,046
Nov 30 - Dec 1
Total with taxes and fees
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Indoor pool, a heated pool
Seasons On Mount Snow - Ski-in/Ski-out

Condo in Dover

9.8 out of 10, Exceptional, (180)
"Nice place to stay "
United States
Dean W.
Seasons On Mount Snow - Ski-in/Ski-out
Interior
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Vacation Home in Dover

10.0 out of 10, Exceptional, (10)
"Everything was really nice! The house was great and the whole place lovely. Great location! The manager was really helpful and easy to get in touch with. He was able to help us with all of our questions. The conditions of the mountain were really good. Wonderful stay! "
United States
Tina S.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
9 bedrooms, desk, iron/ironing board, free WiFi
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Vacation Home in Wardsboro

9.6 out of 10, Exceptional, (28)
"Great place! Great communication with the host. Definitely coming back."
United States
Robert T.
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Terrace/patio
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Vacation Home in Townshend

10.0 out of 10, Exceptional, (6)
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC
Interior
Lovely 2nd Floor Apartment

Vacation Home in Greenfield

10.0 out of 10, Exceptional, (44)
"Our stay was so amazing. The hosts were wonderul and really adapatable to our family needs."
United States
Wendy M.
$181 nightly
The price is $202
Nov 30 - Dec 1
Total with taxes and fees
Lovely 2nd Floor Apartment
Exterior
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

Apartment in Dover

9.4 out of 10, Exceptional, (16)
"So cute and in such a great area! It was a perfect stay"
United States
Jaden F.
$221 nightly
The price is $250
Nov 30 - Dec 1
Total with taxes and fees
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dining
Mount Snow, Hot Tub Room, Sauna, Pool Table, sleeps 12.

Vacation Home in Mount Snow

10.0 out of 10, Exceptional, (17)
"Ken came to the rescue when our original reservation was double booked! He made sure we were taken care in a very quick manner and responded to all of my inquiries timely! "
United States
liz c.
Mount Snow, Hot Tub Room, Sauna, Pool Table, sleeps 12.
Fridge, microwave, stovetop, dishwasher
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

Apartment in Dover

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.
$327 nightly
The price is $370
Nov 30 - Dec 1
Total with taxes and fees
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
Property grounds
Beautiful Lodging at Mount Snow with Hot Tub on Deck

Chalet in Wilmington

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
3 bedrooms, desk, iron/ironing board, travel crib
Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger

Camping in Dover

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.
$450 nightly
The price is $509
Dec 2 - Dec 3
Total with taxes and fees
Mount Snow Yurt: Hot Tub~Wood Stove~WiFi~EVcharger
Dining
The Birch. A Spacious Mansion 2 min from Mt. Snow!

Villa in Dover

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!
1 bedroom, iron/ironing board, WiFi, bed sheets
Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym

Cabin in Wilmington

7.4 out of 10, Good, (8)
"The cabin was a perfect rustic experience for foliage viewing and exploring Wilmington and the nearby areas!! Everything was perfect!"
United States
Tessa A.
Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym
Interior
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Vacation Home in Whitingham

10.0 out of 10, Exceptional, (50)
"Great stay perfect for 2 people, relax on then porch and look at the lake! "
United States
Keith D.
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Fridge, microwave, oven, stovetop
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Vacation Home in Townshend

10.0 out of 10, Exceptional, (62)
"Another great summer vacation with family at this beautiful property! Have already booked for next year."
United States
Shirlee B.
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
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

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

10/10 Excellent
"All good"
gail 1-night trip
Posted 1 day ago
Riverside Hotel, an Ascend Collection Hotel

Find out more about West Chesterfield

Everything you need to know about West Chesterfield vacation rentals

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

West Chesterfield vacation 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 low season months. For more hustle and bustle, you may prefer to visit West Chesterfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $202 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on West Chesterfield rentals

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

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in West Chesterfield?

Yes, you can find vacation rentals close to popular sights in West Chesterfield, or you can select a more secluded option if you'd like a relaxing place to stay. Nature enthusiasts will enjoy the riverfront in West Chesterfield. Make sure you have time to check out the entertainment choices and theaters during your trip.

What's the top vacation rental that West Chesterfield has to offer?

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. : Visitors like this West Chesterfield vacation home rental. It 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a hot tub.

What’s there to see and do in West Chesterfield?

Connecticut River and Madame Sherri Forest are a couple of scenic spots to enjoy the outdoors, whereas Actors Theatre Playhouse is one of the cultural attractions. While here, United States Navy Seabee Bridge and Madame Sherris Castle Ruins are other places worth a visit.

What’s a vacation rental in West Chesterfield like?

Vacation rentals are private properties you can stay in for several days or longer in West Chesterfield. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for families.