Photo by Heather Beaudry

Holiday Rentals in West Chesterfield

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Holiday Rentals in West Chesterfield

Beautiful, private log cabin with huge, relaxing screened porch
10.0 out of 10, Exceptional, (30)
"We had a wonderful, quiet and relaxing time. Plenty of rooms for every guest. The veranda is very special. We will go back again and we would recommend it. The Host, Beth, was welcoming and helpful."
Beautiful, private log cabin with huge, relaxing screened porch
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, (50)
"Great little Chalet and beautiful wooded location. Great for our early fall trip."
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Seasons On Mount Snow - Ski-in/Ski-out
9.8 out of 10, Exceptional, (153)
"Got in on a friday night rather late and appreciated the clear instructions on how to access the condo. Very open and airy feel to the vommon area. Loved the walk put to the back area with patio and babbling brook! Rooms were spacious and plenty of bedding options! Great bathroom in the master!!! Everthing needed was provided! Carl was more then generous with the check out and that was the cherry on top for our family! Great place to stay! Would rent again if coming to the area! Loved the...
Seasons On Mount Snow - Ski-in/Ski-out
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
10.0 out of 10, Exceptional, (28)
"We had a wonderful time staying at the cabin. Enjoyed the space itself and the property. Quiet, private and peaceful. Looking forward to returning in the winter. "
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, (38)
"A friend and I stayed at this location for a few days in the autumn. Everything was as listed and it was perfect for our getaway. I would highly recommend this place for anyone I know looking for a quiet and quaint place to stay!"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Waterfront Cottage on Scenic Sportsman Pond
9.6 out of 10, Exceptional, (39)
"Very clean, very private and secluded. What a hidden gem!"
Waterfront Cottage on Scenic Sportsman Pond
Mount Snow's Best View - Sleeps 8-10
10.0 out of 10, Exceptional, (43)
"The property has great views of the mountain, the place was clean and offered plenty of space. It is located near plenty of restaurant's and across the street from Mt. Snow. The clubhouse is new and was a nice bonus to use. "
Mount Snow's Best View - Sleeps 8-10
The Brown House. Indoor pool - Spa - Sauna - Gameroom
8.2 out of 10, Very good, (22)
"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
Family Friendly Hilltop House In Putney Vermont
9.4 out of 10, Exceptional, (52)
"This is a large property. We were able to relax and enjoy ourselves. The beds were amazing and everything was fresh and clean. Although the owner is on sight, we had complete privacy. The kitchen is well appointed with everything you need to make a wonderful Vermont meal. 10 out of 10. We’d stay again!"
The price is €312
includes taxes & fees
23 Sept - 24 Sept
Family Friendly Hilltop House In Putney Vermont
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.6 out of 10, Excellent, (20)
"Good Condo in a great location"
The price is €252
includes taxes & fees
23 Sept - 24 Sept
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
9.6 out of 10, Exceptional, (39)
"My friends and I book this mansion for our annual getaway and it has become so dear to us. "
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains
9.0 out of 10, Wonderful, (65)
"We loved it and plan to return some day."
Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains
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!
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
10.0 out of 10, Exceptional, (35)
"We read all reviews before we booked and everything said was absolutely accurate. We had a perfect get-away, walking into a beautifully designed and appointed space. Chris is a super host, readily available and responsive to all question and offering fantastic advice on local offerings. Our days started with the best breakfast sandwich ever at his country store, the days ended with extraordinary sunsets and sitting in the hot tub looking at the endless stars. We brought our couch potato dog and...
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
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
Wilmington Family Escape! King Beds, Sleeps 13, Air hockey, Nerfgun Fun
10.0 out of 10, Exceptional, (37)
"We were 10 family members attending a cousins wedding. We loved all the sleeping spaces the kitchen and the bathroom rooms were updated clean and nice. We could walk to town for breakfast or across the street for forgotten items. The neighborhood isn’t beautiful but once inside the house or looking at the backyard- it’s easy to forget that "
The price is €661
includes taxes & fees
23 Sept - 24 Sept
Wilmington Family Escape! King Beds, Sleeps 13, Air hockey, Nerfgun Fun
Green Mountain Modern House: iconic modern getaway
Green Mountain Modern House: iconic modern getaway
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
10.0 out of 10, Exceptional, (207)
"Superb views of the Vermont Mountains and spacious property made this a location my family would love to revisit! We booked Tony's home rather last minute as a Labor Day retreat for my family and several friends, we were blown away by the facilities on-site and closeness to the lake. The kids loved the game room, bicycles, and even tried kayaking by themselves. As a note to perspective renters, this property is about a 1,000ft walk to the lake from the hill the house is based on. Older renters...
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Wilmington Vacation Rental Near Hiking and Skiing!
9.8 out of 10, Exceptional, (11)
"Beautiful cabin! Right in the middle of nature with plenty of things to do nearby. Host was exceptional!"
Wilmington Vacation Rental Near Hiking and Skiing!
Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym
8.0 out of 10, Very good, (2)
"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
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Other types of properties in West Chesterfield you may be interested in

Riverside Hotel, Ascend Hotel Collection
2.5 star property
9.6 out of 10, Exceptional, (538)
"Disappointed that thete was no breakfast available."
The price is €131
includes taxes & fees
21 Oct - 22 Oct
Riverside Hotel, Ascend Hotel Collection
Colonial Motel And Spa
3.0 star property
6.8 out of 10, (1004)
"Fantastic for this regular swimmer to have these lap pools on the property. The place is a bit long in the tooth (worn) but for the price it was a great deal. "
The price is €104
includes taxes & fees
3 Oct - 4 Oct
Colonial Motel And Spa
The Covered Bridge Inn
2.5 star property
8.2 out of 10, Very good, (1005)
"Ok, but tv did not work."
The price is €143
includes taxes & fees
1 Oct - 2 Oct
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.

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?

Mount Snow's Best View - Sleeps 8-10: This holiday home rental outside of West Chesterfield is located in the mountains, and has an indoor pool, a fireplace and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a patio and a terrace.

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, Madame Sherris Castle Ruins 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.