Photo by Heather Beaudry

West Chesterfield Holiday Rentals

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Holiday Rentals in West Chesterfield

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
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, (24)
"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
Cozy Cottage Along Idyllic Green River
Exterior
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, (33)
"Charming house with everything we needed!"
Cozy Cottage Along Idyllic Green River
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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
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)
"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
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)
"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!
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, (8)
"The house was superb for our family visit! We enjoyed it all! Linda was a perfect hostess…,so attentive!"
Troy House, Country Get Away, w fire-pit, rec & game rm, many small ponds 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!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
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, (194)
"Great all around, would book again"
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)
"Beatiful weekend get away."
Wilmington Vacation Rental Near Hiking and Skiing!
Green Mountain Modern House: iconic modern getaway
Exterior
Green Mountain Modern House: iconic modern getaway
Green Mountain Modern House: iconic modern getaway
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, (24)
"Stayed over a long weekend with two families with kids ranging from 11-14. The house was very clean and well stocked. Plenty of towels and sheets and blankets are clean and comfortable. Basement was a great place for the kids to hang out and they enjoyed darts, Pac-Man etc.. Yard and deck areas were great."
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)
"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
Waterfront Cottage on Scenic Sportsman Pond
Exterior
Waterfront Cottage on Scenic Sportsman Pond
9.4 out of 10, Exceptional, (35)
"Had a wonderful weekend kayaking and fishing. Very private and quiet. Great relaxing spot in nature"
Waterfront Cottage on Scenic Sportsman Pond
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)
"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
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."
The price is NZ$910
per night
6 Jun - 7 Jun
Mount Snow's Best View - Sleeps 8-10
Upscale Mount Snow/Stratton Area w/Indoor Pool access, short drive to lakes
Upscale Mount Snow/Stratton Area w/Indoor Pool access, short drive to lakes
10.0 out of 10, Exceptional, (69)
"This was our second time renting in Vermont. I thought the first house was a good fit for our family, until I stayed here. This house is absolutely gorgeous. It feels so warm and cozy. The open space in the kitchen/dining and living room makes it inviting for the adults and kids to be together in one space... which was really nice having 5 toddlers with us. They had condiments in the fridge, which you dont find often. It can be a pain having to run out with toddlers durning dinner time to get...
Upscale Mount Snow/Stratton Area w/Indoor Pool access, short drive to lakes
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
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.

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, (504)
"What a lovely hotel, with the beautiful Connecticut River right next to it. I stayed for six nights and loved waking up to that pretty view. Pleasant and attentive staff, provided recommendations for dining when asked. Bed was comfortable for a nice sleep. Clean room and premises. Highly recommend it. "
The price is NZ$270
per night
30 Jun - 1 Jul
Riverside Hotel, Ascend Hotel Collection
Colonial Motel And Spa
Exterior
Colonial Motel And Spa
3.0 star property
7.0 out of 10, Good, (1002)
"I would definitely come back there again "
The price is NZ$176
per night
3 Jun - 4 Jun
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, (1001)
"This was a clean comfortable place to stay . "
The price is NZ$145
per night
11 Jun - 12 Jun
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our West Chesterfield holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up West Chesterfield. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in West Chesterfield. Seeing all the best attractions is bound to make you fall in love with West Chesterfield. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in West Chesterfield short-term rentals, that won’t be hard to do.

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?

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms: This holiday home rental outside of West Chesterfield is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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, United States Navy Seabee Bridge and Madame Sherris Castle Ruins 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

Holiday Inn Express Keene, an IHG Hotel

Holiday Inn Express Keene, an IHG Hotel

5/5 Excellent
"Clean and quiet."
A verified traveller stayed at Holiday Inn Express Keene, an IHG Hotel
Posted 1 day ago
Holiday Inn Express Keene, an IHG Hotel