Photo by Heather Beaudry

West Chesterfield Vacation Rentals

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Vacation Rentals in West Chesterfield

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

7.6 out of 10, Good, (19)
"Absolutely loved my stay at this tiny getaway house! The space was cozy, well-designed, and had everything I needed for a relaxing escape. The peaceful surroundings and thoughtful touches made it truly special. Perfect for unplugging and recharging. Can’t wait to come back for another retreat!" "
Dog-friendly chalet cabin with valley view, deck, and private hot tub
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, (19)
"My husband and I decided to rent out this property for our reception and could not have been more pleased. The property was perfect for our intimate wedding. It was rustic, quiet, and had a ton of fun activities. The entire home was full of character and each room was unique. The two houses on the property were clean and taken care of, just older so do not expect modern and new. I personally love older rustic locations, especially ones that you know have been lived in and loved. I gave the...
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
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, (43)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
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!

9.0 out of 10, Wonderful, (41)
"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!
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, (21)
"Good Condo in a great location"
The price is CA $178
CA $514 total
includes taxes & fees
Jan 9 - Jan 10, 2025
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, (30)
"Cozy 1 bdrm very close to the slopes. The host are vey cooperative abd get back to you quickly."
Walk to Mount Snow, Cozy, Clean and Comfortable!
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Terrace/patio

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

9.8 out of 10, Exceptional, (41)
"This property is stunning. It fit our group of 14 perfectly. There are so many unique details and beautiful furniture. The kitchen was well-stocked for pots/pans/utensils/cleaning supplies which I always appreciate - makes group meals so much easier to manage. Quiet area, would be great all year round depending on what activities you like. Hot tub was a major highlight!"
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16
Spa

Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16

10.0 out of 10, Exceptional, (21)
"The property is exactly as described! We loved the proximity to the mountain. The house is adorable and perfectly suited for our family. The host was VERY responsive and had great customer service during our stay. We can not wait to come back again!"
Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Interior

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

10.0 out of 10, Exceptional, (40)
"We enjoyed our stay at the tiny home!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
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

8.8 out of 10, Excellent, (3)
"My stay with a friend at this location was extremely pleasant overall; the home was well furnished, stocked, and the surroundings of rural Vermont were beyond gorgeous. The interior was very well cleaned when I arrived, though my friend and I very quickly noticed that there was a distinct septic-like odor in the house's central hallway area and the home's exterior (walking up to the entryway, etc). This smell persisted throughout the duration of the stay, but was most noticeable on days where...
Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym
Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!
Outdoor dining

Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!

10.0 out of 10, Exceptional, (26)
"The house was perfect for a group of five of us. The kitchen and grill were great for our culinary needs. Thanks for letting us stay!"
Secluded, Cozy Cabin on 10 Acres of Woods ~16 mi to Slopes & Pet Friendly!
Green Mountain Modern House: iconic modern getaway
Exterior

Green Mountain Modern House: iconic modern getaway

Green Mountain Modern House: iconic modern getaway
Waterfront Cottage on Scenic Sportsman Pond
Exterior

Waterfront Cottage on Scenic Sportsman Pond

9.6 out of 10, Exceptional, (41)
"Sportsman's Pond and Blueberry Cottage provided the ideal location for disconnecting from the noise and busyness of every day life. The pond was beautifully serene, without outboard motors, jet skis, etc. The fall colors were gorgeous. The hosts provided every sort of watercraft one might want. I kayaked everyday exploring the shoreline and watching for birds. The cottage was well equipped, the bed was comfortable and an assortment of chairs and couches were available for lounging, viewing the...
Waterfront Cottage on Scenic Sportsman Pond
The Jelly Mill-A River Retreat
Exterior

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (43)
"It is a beautiful home with a ton of space (we only had 3 people, but it easily sleeps 6), very clean and well-kept. Our hosts provided everything we needed to make our stay perfect. I also like that the hosts were not overboard with all the rules, as with some other rentals. The hosts were beyond friendly and had excellent communication throughout the whole process. If you are looking for a lovely home with a ton of space to stay while exploring Vermont and Massachusetts, I highly recommend...
The Jelly Mill-A River Retreat
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun
Outdoor spa tub

Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun

10.0 out of 10, Exceptional, (41)
"We stayed for Thanksgiving week. The house was more than big enough for our group of nine. The open kitchen/living room/dining room worked great for preparing and eating Thanksgiving dinner together. My wife identified an issue with the outdoor gas grill; the hosts had the grill replaced quickly and we were able to use it as planned. The hosts were very responsive and helpful. We would definitely stay here again."
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun
The Brown House. Indoor pool - Spa - Sauna - Gameroom
Outdoor spa tub

The Brown House. Indoor pool - Spa - Sauna - Gameroom

8.0 out of 10, Very good, (23)
"It was our yearly Guys weekend, everyone had a Great time. The house with every bedroom having a full bath was fantastic you couldn’t ask for more We spent many hours in the indoor pool and the 2 jacuzzi’s we will definitely stay there again"
The Brown House. Indoor pool - Spa - Sauna - Gameroom
Jacksonville Cabin w/ Wraparound Deck & Views
Interior

Jacksonville Cabin w/ Wraparound Deck & Views

9.6 out of 10, Exceptional, (27)
"We enjoyed our stay. Everything was clean. The only thing I would suggest is checking the stairs to the basement. "
Jacksonville Cabin w/ Wraparound Deck & Views
Family Friendly Hilltop House In Putney Vermont
Exterior

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (53)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is CA $280
CA $494 total
includes taxes & fees
Dec 27 - Dec 28
Family Friendly Hilltop House In Putney Vermont
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, (158)
"This was possibly one of the best VRBO experiences for me. Flawless in all respects"
Seasons On Mount Snow - Ski-in/Ski-out
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

6.6 out of 10, (12)
"My boyfriend and I (and our dog) really enjoyed this place. It’s on a quiet road, tucked up into a woodsy hill which gives the feeling of being secluded, while in actuality not being far from a main road. The listing is pretty accurate; the house is absolutely covered in windows, which allows for plenty of fresh air and natural light. The master bed is super comfortable, and the master bathroom is really nice too. I was a little apprehensive about the lack of air conditioning, but there is a...
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck
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 drapes

Riverside Hotel, Ascend Hotel Collection

2.5 star property
9.6 out of 10, Exceptional, (555)
"This is one of our favorite hotels to stay at."
The price is CA $206
CA $224 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Riverside Hotel, Ascend Hotel Collection
Mountaineer Inn
Fireplace

Mountaineer Inn

2.0 star property
9.0 out of 10, Wonderful, (354)
"We had an amazing day of skiing, a wonderful dinner at the Snow Republic Brewery and then an extremely quiet, comfortable night at Mountaneer. We will be back soon!!!!"
The price is CA $225
CA $272 total
includes taxes & fees
Jan 5 - Jan 6, 2025
Mountaineer Inn
Colonial Motel And Spa
Exterior

Colonial Motel And Spa

3.0 star property
6.8 out of 10, (1001)
"Like size of room"
The price is CA $141
CA $155 total
includes taxes & fees
Jan 1 - Jan 2, 2025
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 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?

Dog-friendly chalet cabin with valley view, deck, and private hot tub: Visitors like this West Chesterfield vacation home rental. It offers a patio, a selection of games, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the spa tub in this rental home to help you unwind.

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

Connecticut River and Madame Sherri Forest 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 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.