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Search Holiday Rentals in West Chesterfield

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May 2 - May 3
Tomorrow
May 3 - May 4
This weekend
May 3 - May 5
Next weekend
May 10 - May 12

Top Holiday 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
9.2 out of 10, Wonderful, (23)
"Awesome cabin, fireplace was amazing. Spacious open and a great place to spend time and relax"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
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)
"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
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, (192)
"Our family rated this as our best stay in 7 years of traveling with VRBO properties. There was lots of room for everyone to spread-out, but the family spent most of the time in the game room playing pool, fuzzball, shuffleboard and Ping-Pong. Overall and great spring break for the family and friends."
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
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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, (16)
"Our experience was average overall."
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Seasons On Mount Snow - Ski-in/Ski-out
Indoor pool, a heated pool
Seasons On Mount Snow - Ski-in/Ski-out
9.8 out of 10, Exceptional, (148)
"Carl was super nice, proactive, and a great communicator for this trip. The place was convenient, clean, in great repair, with lots of amenities and super easy to ski out. Little touches like a box of firewood, tinder, and matches and clear instructions on everything make things so pleasant. Would totally stay again. "
Seasons On Mount Snow - Ski-in/Ski-out
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, (24)
"The house was very comfortable for our family. It was well-stocked with plates, pots, and pans. Bed were comfortable."
Beautiful, private log cabin with huge, relaxing screened porch
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, (38)
"The vrbo was as-described and the hosts exceptionally personable and friendly. Exemplary!"
Spectacular Mountain views with all the amentities nearby
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!
9.0 out of 10, Wonderful, (37)
"Property was incredible. The house was beautiful and enormous. Very comfortable with a group of 22. Pool and hot tub were great."
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
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)
"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!"
The price is £360
per night
6 May - 7 May
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
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
7.4 out of 10, Good, (12)
"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
Green Mountain Modern House: iconic modern getaway
Exterior
Green Mountain Modern House: iconic modern getaway
Green Mountain Modern House: iconic modern getaway
Cozy Cottage Along Idyllic Green River
Exterior
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, (32)
"Perfect litle getaway. Not to far from town, beautiful surrounding area, exactly what i was looking for."
Cozy Cottage Along Idyllic Green River
Cozy Treetop Hideaway Near Harriman Reservoir!
Fridge, microwave, stovetop, cookware/dishes/utensils
Cozy Treetop Hideaway Near Harriman Reservoir!
9.8 out of 10, Exceptional, (10)
"The house was a very cute ski cabin-y feeling vacation spot with a gorgeous view of the reservoir. Location was great- not too far from the center of Wilmington. And a drive through the mountains/National Forest away from the other cities/tourist areas near Bennington. It snowed while we were staying and the owners stayed on top of plowing so we could drive in and out - they weren't kidding about needing 4WD to get in and out in the winter. Overall, we'd come back in a heartbeat"
Cozy Treetop Hideaway Near Harriman Reservoir!
Waterfront Cottage on Scenic Sportsman Pond
Exterior
Waterfront Cottage on Scenic Sportsman Pond
9.4 out of 10, Exceptional, (34)
"Linda was wonderful in her review of the property and was very accommodating in all aspects of our stay. The cottage was well equipped and very comfortable including the mattress. We enjoyed the lake and a little fishing. The area is very nice and we did some exploring. It was very quiet and we rarely even saw anyone while we were on the lake. We hope to return in the spring or summer. Many thanks to Linda and Brad"
Waterfront Cottage on Scenic Sportsman Pond
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)
"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
Mount Snow's Best View - Sleeps 8-10
Fridge, microwave, oven, stovetop
Mount Snow's Best View - Sleeps 8-10
10.0 out of 10, Exceptional, (39)
"We loved this condo! It was so gorgeous and clean, and has an awesome view of the mountain. There was so much space and all of our needs were met! We would go back again for sure."
Mount Snow's Best View - Sleeps 8-10
Jacksonville Cabin w/ Wraparound Deck & Views
Fridge, microwave, stovetop, dishwasher
Jacksonville Cabin w/ Wraparound Deck & Views
9.6 out of 10, Exceptional, (23)
"Magical little place."
Jacksonville Cabin w/ Wraparound Deck & Views
Family Friendly Hilltop House In Putney Vermont
Exterior
Family Friendly Hilltop House In Putney Vermont
9.6 out of 10, Exceptional, (50)
"The house was excellent and the view of the pond was amazing! But what we appreciated the most was Michele's help and communication about the snowstorm that was set to hit the area. She had excellent info and advice and was able to move our stay up a day so we could stay ahead of the storm. We had a great trip to Vermont and very much appreciate her help!"
The price is £268
per night
7 May - 8 May
Family Friendly Hilltop House In Putney Vermont
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Property grounds
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.6 out of 10, Excellent, (18)
"This location was great. Having the clubhouse with access to the pool is an added bonus. We would definitely book again in the future."
The price is £274
per night
5 May - 6 May
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Walk to Mount Snow, Cozy, Clean and Comfortable!
Pool
Walk to Mount Snow, Cozy, Clean and Comfortable!
9.6 out of 10, Exceptional, (27)
"Great place to stay and our second time staying here!"
Walk to Mount Snow, Cozy, Clean and Comfortable!
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 Holiday Rental Travel Info

Number of holiday rentals
3
Popular accommodation
West Chesterfield private holiday 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 curtains
Riverside Hotel, Ascend Hotel Collection
2.5 star property
9.6 out of 10, Exceptional, (502)
"Nice clean large rooms, public space. No food, snacks (that I could find) but good coffee and tea in the AM. Accomodating staff. Would stay again. "
The price is £146
per night
22 May - 23 May
Riverside Hotel, Ascend Hotel Collection
The Covered Bridge Inn
Concierge desk
The Covered Bridge Inn
2.5 star property
8.2 out of 10, Very good, (1003)
"Plenty of restaurants, very clean and updated rooms."
The price is £78
per night
2 Jun - 3 Jun
The Covered Bridge Inn
Colonial Motel And Spa
Exterior
Colonial Motel And Spa
3.0 star property
7.0 out of 10, Good, (1001)
"Very comfortable "
The price is £88
per night
5 May - 6 May
Colonial Motel And Spa
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 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, apart-hotels, 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 favorite 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 depends 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 £268 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 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’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, Connecticut River and Wantastiquet Mountain 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.

Recent reviews of West Chesterfield properties
Expedia verified reviews

Hampton Inn & Suites Keene

Hampton Inn & Suites Keene

5/5 Excellent
"The room was comfortable and clean. Breakfast was great "
A verified traveller stayed at Hampton Inn & Suites Keene
Posted 3 days ago
Hampton Inn & Suites Keene