Photo by Heather Beaudry

West Chesterfield Holiday Rentals

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Check prices for these dates

Tonight
19 Feb - 20 Feb
Tomorrow
20 Feb - 21 Feb
This weekend
21 Feb - 23 Feb
Next weekend
28 Feb - 2 Mar

Holiday Rentals in West Chesterfield

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

Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym

7.0 out of 10, Good, (6)
"Dining shopping not too far, but not walkable. The amount we paid was more than double the advertised price, yet we were still asked to perform a laundry list of cleaning tasks before exiting the unit (vacuuming, folding blankets, emptying and taking out gargage, etc.). I realize there is likely a management fee, but most VRBO properties do not require anything more than making sure doors and windows are secure, sink is clear, thermostats set at certain temps, etc. The property is also in...
Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!
Outdoor dining

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

10.0 out of 10, Exceptional, (44)
"From its warmth, fireplace, chalkboard for fun with friends, lots of games and super convenient location to Mount Snow – this place is a must stay! We can’t wait to come back."
The price is AU$574
includes taxes & fees
19 Mar - 20 Mar
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!
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

8.8 out of 10, Excellent, (45)
"A great little cabin close to Mt. Snow. Accurate description. Fire place didn’t work. Would stay here again. "
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-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

7.0 out of 10, Good, (14)
"Great place. Clean and comfortable. Nicely stocked kitchen with newer appliances. Sauna was amazing. Had 10 inches of snow one morning and it was fully plowed by 7am!"
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Outdoor spa tub

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

8.8 out of 10, Excellent, (42)
"We had a group of thirty-four people for a family vacation and had a blast. The host and the housekeeper were tremendously responsive to any small issues we had over the first few days. The kitchen was well stocked but could use more mugs for coffee/tea and additional forks for larger groups and the tea bags were past the best before date and should be replaced. Twelve bedrooms, each with their own bathroom was great. The pool, hot tubs, ping pong table, pool table, tennis court, and fire pit...
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Updated Ski in ski out condo & mountain biking located at Seasons on Mt. Snow
Terrace/patio

Updated Ski in ski out condo & mountain biking located at Seasons on Mt. Snow

10.0 out of 10, Exceptional, (51)
"Really loved the location of this property! Ski on/ski off was amazing! The property was great, exactly as pictured and we would love staying here again in the future!"
Updated Ski in ski out condo & mountain biking located at Seasons on Mt. Snow
MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain Den
Exterior

MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain Den

9.4 out of 10, Exceptional, (13)
"Would have given 5-stars but the location is right below another rental and you can hear everyone walking around, which was a little annoying. After a friendly visit to the upstairs neighbors, and a cordial chat, it was a great evening. If the upstairs came with padded carpet this place would be a home run."
The price is AU$398
includes taxes & fees
3 Mar - 4 Mar
MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain Den
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, (51)
"This place was just about perfect with excellent hosts that were easy to communicate to. My only ask would be to get shades to block the sun in the morning in the bedroom to the left of the upstairs bathroom. We did not use that bedroom because of this reason. That being said, we loved this place so much that we already booked again for next year. "
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
TV, fireplace, DVD player, books

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

9.8 out of 10, Exceptional, (113)
"Great place to stay with friends and family. Will be visiting again!"
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!
MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain House
Terrace/patio

MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain House

10.0 out of 10, Exceptional, (13)
"Six of us women from Vermont golf courses stayed while playing a tournament at Haystack Country Club. The house suited us perfectly. We had some issues with the bathtub plumbing not turning off but we had prompt attention from a service person. The house had a great kitchen and tv to accommodate us."
The price is AU$590
includes taxes & fees
17 Mar - 18 Mar
MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain House
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, (24)
"The apartment was in a great location to get to the ski lifts. "
The price is AU$475
includes taxes & fees
27 Feb - 28 Feb
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
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, (21)
"ideal for a large group of adult friends "
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
Wilmington Vacation Rental Near Hiking and Skiing!
TV, fireplace, books

Wilmington Vacation Rental Near Hiking and Skiing!

9.2 out of 10, Wonderful, (17)
"Perfect weekend house close to mt snow"
Wilmington Vacation Rental Near Hiking and Skiing!
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
Fridge, microwave, stovetop, dishwasher

Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn

9.6 out of 10, Exceptional, (4)
"We had a mixed experience during our stay at Leah's property. On the positive side, Leah was an incredibly friendly and communicative host. She was quick to respond to any questions, and the location was absolutely fantastic—very convenient and close to everything.However, upon arrival, we noticed the unit wasn’t as clean as we expected. There were stains on the rug, dust on the furniture, crumbs on the coffee table, and a dirty stovetop. The dishes appeared to have been used but weren’t...
The price is AU$793
includes taxes & fees
25 Feb - 26 Feb
Mt. Snow Condo with Pool-Mountain Views <1/2 mile to mtn
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, (213)
"Our annual family ski vacation is always at Mt Snow. This year we were lucky enough to spend a week at Tony and Jeanette’s home. Which is exactly as we felt - at home. The house is beautiful and the amenities perfect. The home was clean, guest linens and towels, paper goods all provided. We loved the view and the binoculars!! We would love to stay again. "
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Mountain-view home near the slopes with at-home entertainment - dog-friendly
Fridge, microwave, oven, stovetop

Mountain-view home near the slopes with at-home entertainment - dog-friendly

7.8 out of 10, Good, (65)
"The location was excellent. Five mins from to Mt. Snow. Nice game room but needs attention. Dartboard unusable - only 2 darts with no flights useless. Nice pool table but queues were poor and no chalk. Ping pong was almost too tight to be usable. Kitchen needs serious upgrade. Lots of pots and pans but all well aged. Overall the place could be a place we'd return to but needs upgrades."
Mountain-view home near the slopes with at-home entertainment - dog-friendly
New Renovated Ski Chalet on the River with a Hottub
Interior

New Renovated Ski Chalet on the River with a Hottub

10.0 out of 10, Exceptional, (2)
"Conor was very easy to get in touch with. The location of the place was ideal!"
New Renovated Ski Chalet on the River with a Hottub
Cozy retreat near slopes
Spa

Cozy retreat near slopes

4.4 out of 10, (7)
"Unit is a little outdated but nice.Not truly a ski in - out since you have to walk on the road about 200 yards to get to the Sachem trail.Condo does need ice cube trays since the ice maker is not working.Also the down stairs bath room heater does not work and would be nice since this is where the bath tub is located"
Cozy retreat near slopes
Dog-friendly cabin with pools, hot tub, tennis & pickleball - near Mt. Snow
Fridge, microwave, oven, stovetop

Dog-friendly cabin with pools, hot tub, tennis & pickleball - near Mt. Snow

8.8 out of 10, Excellent, (3)
"We had an awesome stay! Clean house"
Dog-friendly cabin with pools, hot tub, tennis & pickleball - near Mt. Snow
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, (5)
"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! "
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
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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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, (559)
"This is one of our favorite hotels to stay at."
The price is AU$245
includes taxes & fees
3 Mar - 4 Mar
Riverside Hotel, Ascend Hotel Collection
Mountaineer Inn
Fireplace

Mountaineer Inn

2.0 star property
9.0 out of 10, Wonderful, (411)
"Food choice limited for continental breakfast. staff friendly. pool table had torn felt and 2 sets of balls."
The price is AU$234
includes taxes & fees
3 Mar - 4 Mar
Mountaineer Inn
Colonial Motel And Spa
Exterior

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1000)
"All ok everything worked well just older decor "
The price is AU$189
includes taxes & fees
24 Feb - 25 Feb
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.

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?

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!: This holiday home rental outside of West Chesterfield is located in the mountains, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of books.

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.