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West Chesterfield Vacation Rentals

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Vacation Rentals in West Chesterfield

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, 26 reviews
"Very cozy little house, close to everything, great hikes, and downtown was very cute!"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Fridge, microwave, oven, stovetop
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, 28 reviews
"This is a great spot for a getaway! The space was spotless. There was a lot of privacy. The location was close to everything we needed. The space is cozy and super fun with the hot tub and fore pit! We we are able to enjoy the included breakfast, which was great before skiing!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Interior
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, 47 reviews
"We loved our stay at the chalet. It's perfectly situated in the cutest little neighborhood, while also feeling very secluded. The chalet had everything we needed for our stay. While visiting we walked a few of the trails nearby, part of the Valley Trail and the Hoot, Toot and Whistle. They were both perfect for our pups, especially during hunting season. We gave our pups an extra squeeze in honor of Scarlet. Thank you for sharing your place with us! We would love to stay again!!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
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Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Exterior
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
10.0 out of 10, Exceptional, 39 reviews
"My husband and I wanted a relaxing few days to get away from our hectic lives. This small cabin was perfect, comfortable, and nicely appointed. Reading a book on the screened in porch with a cup of coffee was my favorite part. It is a quiet place in the woods but close to many small and quaint towns to visit in Vermont. The Newfane Store a few miles down the road was a great place to grab a coffee and meal. I also really appreciate that I could bring my dog. Many thanks for a warm and cozy...
Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT
Cozy Cottage Along Idyllic Green River
Exterior
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, 37 reviews
"The beautiful drive to this location was worth the trip! Lovely on every account! The tips for local sights and activities made us wish we were there longer!"
Cozy Cottage Along Idyllic Green River
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9 bedrooms, desk, iron/ironing board, free WiFi
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9.4 out of 10, Exceptional, 17 reviews
"Definitely recommend this place for large groups. Very clean, so much to do, and great communication with host. Very private location"
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Beautiful, private log cabin with huge, relaxing screened porch
Property grounds
Beautiful, private log cabin with huge, relaxing screened porch
10.0 out of 10, Exceptional, 25 reviews
"We had a great stay at Labrador Lodge! The house was comfortable and cozy. The layout of the home worked perfectly for our family and we loved being together on the quiet mountain road. The beautiful, large screen porch was our favorite part!"
Beautiful, private log cabin with huge, relaxing screened porch
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Fridge, microwave, stovetop, coffee/tea maker
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
10.0 out of 10, Exceptional, 22 reviews
"This property is fairytale cute, so welcoming and relaxing. We had a beautiful stay in Vermont thanks to this location. And there were surprise puppies on site!!!!! Honestly this was the kind of trip that gives you confidence in vacation rentals. Clean, wonderfully decorated, off the beaten path a truly relaxing stay! Go outside at night!!!! We dont have stars like that in the city."
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
The Brown House. Indoor pool - Spa - Sauna - Gameroom
Fridge, microwave, oven, stovetop
The Brown House. Indoor pool - Spa - Sauna - Gameroom
8.0 out of 10, Very good, 19 reviews
"We had a large crew and this house had plenty of room for all. Large table and lots of room to hang out. The location to the mountain is great- so close! You can walk through the snow to a restaurant. Unfortunately, the new pool was not ready yet, but it looks like it will be gorgeous and we would come back again."
The Brown House. Indoor pool - Spa - Sauna - Gameroom
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Lake
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
10.0 out of 10, Exceptional, 9 reviews
"The grounds were well kept. The house was remodeled and very clean. Lots of room. Equipped with everything you would need. Quiet. Owners were awesome to deal with and easy to get ahold of. I would definitely recommend people to stay there. "
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds nearby
Spectacular Mountain views with all the amentities nearby
1 bedroom, iron/ironing board, free WiFi, bed sheets
Spectacular Mountain views with all the amentities nearby
9.8 out of 10, Exceptional, 41 reviews
"The property was exactly what I was expecting. Check-in was simple and the property was very clean."
Spectacular Mountain views with all the amentities nearby
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Property grounds
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
10.0 out of 10, Exceptional, 197 reviews
"The site was exceptionally beautiful and the host was very helpful and easy to contact."
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Wilmington Vacation Rental Near Hiking and Skiing!
TV, fireplace, books
Wilmington Vacation Rental Near Hiking and Skiing!
10.0 out of 10, Exceptional, 9 reviews
"Beatiful weekend get away."
Wilmington Vacation Rental Near Hiking and Skiing!
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Property grounds
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
8.8 out of 10, Excellent, 38 reviews
"The home location, layout were awesome. Pics must be older as there was maintenance needed on the basketball/tennis court, pool, and shuffleboard room. Our bachelor party had a good time, once some updates are done, could be a 5 start spot."
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!
Property grounds
Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!
10.0 out of 10, Exceptional, 25 reviews
"Great home, truly beautiful surroundings and easy drive to lots of stuff. We tackled Mass MoCA, kayaking in Brattleboro and mountain adventures at Bromley. Plus all the small towns and pit stops along the way. Very family friendly house with basement for older kids and well child-proofed for any youngsters."
Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
Fridge, microwave, oven, stovetop
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
6.0 out of 10, 8 reviews
"We loved staying in the Newfane home! I was a bit worried at 1st from reading the reviews but it was great. The house was nice and cozy. The sauna and steam tub were AMAZING. We really enjoyed the quiet and we were so close to such great restaurants. We would love to come back!"
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
Cozy Falls Brook Cabin: Hike & Swim On-Site!
Fridge, microwave, stovetop, coffee/tea maker
Cozy Falls Brook Cabin: Hike & Swim On-Site!
10.0 out of 10, Exceptional, 4 reviews
"What a beautiful clean cabin nestled next to a brook with lots of hiking paths to explore. Centrally located to several ski resorts. Matt was the most excellent host! I look forward to returning during other seasons!"
Cozy Falls Brook Cabin: Hike & Swim On-Site!
Rustic Retreat: Cozy Log Cabin
Property grounds
Rustic Retreat: Cozy Log Cabin
9.6 out of 10, Exceptional, 5 reviews
"It was so peaceful and restful, we didn't even want to go anywhere else and do anything, but stay at the cabin and relax."
Rustic Retreat: Cozy Log Cabin
Dog-friendly chalet cabin with valley view, deck, and private hot tub
TV
Dog-friendly chalet cabin with valley view, deck, and private hot tub
7.2 out of 10, Good, 14 reviews
"We had a great weekend staying here. The projector and hot tub were awesome amenities. There was a snow storm right before we arrived and the roads were clear and the driveway was plowed. We had a great experience and would stay here again!"
Dog-friendly chalet cabin with valley view, deck, and private hot tub
Spacious Mount Snow condo near slopes with private hot tub, sauna & fireplace
Interior
Spacious Mount Snow condo near slopes with private hot tub, sauna & fireplace
8.4 out of 10, Very good, 12 reviews
"Property was great. We were there to ski at Mt Snow and the location did not disappoint. We were not ski-on ski-off but were so close it didn’t matter. Overall the house was clean and the owner was super responsive. Have it saved to stay again next season."
Spacious Mount Snow condo near slopes with private hot tub, sauna & fireplace
Don't see what you're looking for?
See all available properties in West Chesterfield
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.

West Chesterfield Vacation Rental Travel Info

Number of vacation rentals
3
Popular accommodation
West Chesterfield private vacation homes
Known landmarks
Pisgah State Park, Actors Theatre Playhouse and Spofford Lake
International airports
Boston, MA (BOS-Logan Intl.) and Manchester, NH (MHT-Manchester-Boston Regional)

Other types of properties in West Chesterfield you may be interested in

Riverside Hotel, Ascend Hotel Collection
Select Comfort beds, in-room safe, desk, blackout drapes
Riverside Hotel, Ascend Hotel Collection
2.5 star property
9.6 out of 10, Exceptional, 511 reviews
"A very nice stay. The room was large and very clean with a nice river view. Would have liked some type of breakfast service but it was not offered other then coffee."
The price is CA $208
CA $226 total
includes taxes & fees
Jul 25 - Jul 26
Riverside Hotel, Ascend Hotel Collection
Colonial Motel And Spa
Exterior
Colonial Motel And Spa
3.0 star property
6.8 out of 10, 1,004 reviews
"Great spot"
The price is CA $120
CA $133 total
includes taxes & fees
Jul 3 - Jul 4
Colonial Motel And Spa
The Covered Bridge Inn
Concierge desk
The Covered Bridge Inn
2.5 star property
8.2 out of 10, Very good, 1,000 reviews
"Saw some recent negative reviews, but we had a very different experience. The guy at the desk was friendly and helpful, the room was clean and comfortable. Ours was just a 1-night stay, and we have no complaints. Yes, we would stay here again."
The price is CA $150
CA $165 total
includes taxes & fees
Jul 8 - Jul 9
The Covered Bridge Inn
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.

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A West Chesterfield vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of West Chesterfield vacation rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard 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. 

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?

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included: You might want to consider this vacation home rental near West Chesterfield, which 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 a spa tub.

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

Madame Sherri Forest and Connecticut River are a couple of scenic spots to enjoy the outdoors, whereas Actors Theatre Playhouse is one of the cultural attractions. While here, Madame Sherris Castle Ruins and West River 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.

Recent reviews of West Chesterfield properties
Expedia verified reviews

The Covered Bridge Inn

The Covered Bridge Inn

5/5 Excellent
"Saw some recent negative reviews, but we had a very different experience. The guy at the desk was friendly and helpful, the room was clean and comfortable. Ours was just a 1-night stay, and we have no complaints. Yes, we would stay here again."
A verified traveller stayed at The Covered Bridge Inn
Posted 2 days ago
The Covered Bridge Inn