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West Chesterfield Vacation Rentals

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Oct 10 - Oct 12
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Oct 24 - Oct 26
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Dec 19 - Dec 21

Vacation Rentals in West Chesterfield

Our top choices for West Chesterfield vacation rentals

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Outdoor dining

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.4 out of 10, Very Good, (58)
"Great location and super cute"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
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, (174)
"Wonderful host / fantastic location "
Seasons On Mount Snow - Ski-in/Ski-out
Beautiful Lodging at Mount Snow with Hot Tub on Deck
Property grounds

Beautiful Lodging at Mount Snow with Hot Tub on Deck

9.4 out of 10, Exceptional, (42)
"Real Vermont feel. Pretty and nice quiet neighborhood!"
Beautiful Lodging at Mount Snow with Hot Tub on Deck
Owl's Nest Treehouse
Property grounds

Owl's Nest Treehouse

10.0 out of 10, Exceptional, (8)
"This place is beautiful! It had everything we needed. The hosts were very communicative and encouraged us to contact them if we had any questions. We stayed at the treehouse to celebrate our 30th anniversary and it exceeded our expectations. I would highly recommend this cozy and quiet retreat."
The price is ￥40,593
￥49,489 total
includes taxes & fees
Sep 29 - Sep 30
Owl's Nest Treehouse
Lovely 2nd Floor Apartment
Interior

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (36)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
The price is ￥17,138
￥29,697 total
includes taxes & fees
Sep 25 - Sep 26
Lovely 2nd Floor Apartment
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!
Interior

Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

10.0 out of 10, Exceptional, (84)
"A beautiful cabin in the woods. Very clean and a perfect stay."
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!
Cozy Updated Log Cabin with Mountain Views close to Monadnock
Exterior

Cozy Updated Log Cabin with Mountain Views close to Monadnock

9.4 out of 10, Exceptional, (26)
"a fantastic weekend getaway in the mountains! quiet neighborhood with stunning night time views of the stars. such a cozy cabin, very clean, linens provided, nice property with a little fire pit too! very friendly host, easy to contact and pleasant. "
Cozy Updated Log Cabin with Mountain Views close to Monadnock
The Jelly Mill-A Peaceful River Retreat
Exterior

The Jelly Mill-A Peaceful River Retreat

10.0 out of 10, Exceptional, (59)
"Very much off the beaten path, but lets you experience the beauty of Vermont. Quiet and peaceful. A beautiful little property that served our needs perfectly. Would definitely come back."
The Jelly Mill-A Peaceful River Retreat
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Interior

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

10.0 out of 10, Exceptional, (7)
"Great house, great location, Great communication with Todd. Will be back for sure!!!! Thanks for everything Todd. "
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Interior

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

10.0 out of 10, Exceptional, (224)
"Great house, fantastically well equipped (kayaks, bikes etc). Excellent, very responsive host. View out over the lake is amazing. Really enjoyed our stay. "
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Wellness Getaway with a Personal Sauna, and Private River Beach!
Sauna

Wellness Getaway with a Personal Sauna, and Private River Beach!

2.0 star property
10.0 out of 10, Exceptional, (1)
"The folks are SUPER and made me feel very welome"
The price is ￥19,927
￥37,693 total
includes taxes & fees
Sep 30 - Oct 1
Wellness Getaway with a Personal Sauna, and Private River Beach!
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Property grounds

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

10.0 out of 10, Exceptional, (5)
"We had a magical time at the yurt! Very sweet and rustic but comfortable. Great secluded location but close enough to restaurants and Brattleboro. We will definitely be back. "
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Fridge, microwave, oven, stovetop

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

10.0 out of 10, Exceptional, (60)
"We had so much fun between swimming and having a fire . The place is beautiful and private and yet not to far from everything."
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Beautiful Custom Built Timber Frame Home, Sleeps 11
Smart TV, fireplace, DVD player, table tennis

Beautiful Custom Built Timber Frame Home, Sleeps 11

10.0 out of 10, Exceptional, (106)
"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"
Beautiful Custom Built Timber Frame Home, Sleeps 11
Waterfalls-View-Pond. Secluded Vermont Log Cabin at Mount Snow. EV Outlet
Fridge, microwave, oven, stovetop

Waterfalls-View-Pond. Secluded Vermont Log Cabin at Mount Snow. EV Outlet

10.0 out of 10, Exceptional, (81)
"Perfectly clean and welcoming cabin. Comfy beds, great location. Would definitely return. "
Waterfalls-View-Pond. Secluded Vermont Log Cabin at Mount Snow. EV Outlet
Cozy 2-bedroom cabin near Mount Snow 3 min drive
Fridge, microwave, oven, stovetop

Cozy 2-bedroom cabin near Mount Snow 3 min drive

2.0 star property
9.6 out of 10, Exceptional, (8)
"I really enjoyed every aspect of my stay here and highly recommend the property. "
Cozy 2-bedroom cabin near Mount Snow 3 min drive
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior

2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

9.4 out of 10, Exceptional, (16)
"So cute and in such a great area! It was a perfect stay"
The price is ￥6,855
￥39,103 total
includes taxes & fees
Oct 14 - Oct 15
2BR 2BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Bright three-level home with water views, jetted tub, firepit, and pool table
Fridge, microwave, oven, stovetop

Bright three-level home with water views, jetted tub, firepit, and pool table

8.6 out of 10, Excellent, (34)
"Quite secluded clean comfy cabin We enjoyed it very much. Very close to the things we wanted to do."
Bright three-level home with water views, jetted tub, firepit, and pool table
Beautiful, private log cabin with huge, relaxing screened porch
Outdoor dining

Beautiful, private log cabin with huge, relaxing screened porch

10.0 out of 10, Exceptional, (39)
"The spot was amazing and everything was exactly what we wanted. "
Beautiful, private log cabin with huge, relaxing screened porch
Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+
Dining

Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+

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...
Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+
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

Chalet 239

Chalet 239

10/10 Excellent
"I was pleasantly surprised in how well well-maintained this property was. Beautiful decor, impeccably clean, and extremely comfortable bed and linens. We were in a king room with a little deck off the back. It was just lovely to sit outside and have a glass of wine. Check in and check out was a breeze and this adorable hotel is in a perfect location. I would definitely stay here again and recommend to others. "
Dawn 1-night trip
Posted 3 days ago
Chalet 239

Find out more about West Chesterfield

Find out more about West Chesterfield

Search for holiday rentals in West Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in West Chesterfield using one of the methods below:

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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?

Lovely 2nd Floor Apartment: Visitors like this West Chesterfield vacation home rental. It offers a garden, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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 United States Navy Seabee Bridge 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.