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Holiday Rentals in West Chesterfield

"Upon reserving the property, I sent an email to the owner and requested an early checkin, he responded very quickly and accomodated my request. The check in process was very easy, and the property was very clean. The only issue was the hot tub was not installed and functioning dury my stay, which I specifically asked for. The inside of the condo was very clean and the owner provided everything you needed. The only downside was the outside of the property was a little run down and needed some...

"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...

"This was possibly one of the best VRBO experiences for me. Flawless in all respects"

"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."

"This was our second visit to the chalet. It was just as wonderful as the first time. The chalet is incredibly cute and cozy. It's location is perfect for a quiet getaway, while also being very close to downtown Wilmington and many hiking trails. I would highly recommend!"

"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!"

"Amazing place. Offered everything we needed and more. Very warm and comfortable. Well appointed too. We will be back for a longer stay in 2025. "

9 bedrooms, desk, iron/ironing board, free WiFi

"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...

"We enjoyed our stay at the tiny home!"

"The cabin was the perfect weekend getaway. We had issues with connecting the projector to the internet and finally gave up on trying to connect but other then that the overall experience was great. Will be staying here again in the future. "

"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. "

"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!"

"Beautiful cabin! Right in the middle of nature with plenty of things to do nearby. Host was exceptional!"

1 bedroom, iron/ironing board, WiFi, bed sheets

"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...

"My husband and i enjoyed our stay. The cabin was very clean and comfortable. We would definitely rent it again."

"Great place, game room provided many laughs. It was clean, nice quite private property. We will stay again"

"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...

"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"

"We enjoyed our stay. Everything was clean. The only thing I would suggest is checking the stairs to the basement. "

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Other types of properties in West Chesterfield you may be interested in

Select Comfort beds, in-room safe, desk, blackout curtains

"Beautiful view "

includes taxes & fees

9 Dec - 10 Dec

"The staff are nice "

includes taxes & fees

1 Dec - 2 Dec

"Easiet and nicest place ive stayed in a while"

includes taxes & fees

22 Dec - 23 Dec

Find out more about West Chesterfield

Everything you need to know about West Chesterfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the West Chesterfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect West Chesterfield holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

West Chesterfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in West Chesterfield. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A West Chesterfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of West Chesterfield holiday rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on West Chesterfield rentals

At Expedia, we put the best West Chesterfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top West Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream West Chesterfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around West Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Recent reviews of West Chesterfield properties

Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel

5/5 Excellent

"Sat outside for a few minutes at a table and chairs at the fire was awesome. The person at check in was extremely welcoming, cookies in the lobby. People relaxing. Inside looks pretty and clean. Beds are pretty comfy, room is spacious. They accommodated my requests. The little store downstairs is perfect, have snacks, frozen meals, earrings and.. post cards!!!! Only a couple things is that the showers maybe need to be recocked? They look they arent as nice as everything else.Will definitely stay here again. Excited for breakfast. "

A verified traveller stayed at Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel

Posted 3 days ago

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 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW! : This holiday home rental outside of West Chesterfield offers an indoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 12 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 balcony, a garden and a pool table so that you can immerse yourself in your holiday.

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 West River 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.

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Holiday Rentals in West Chesterfield

Check West Chesterfield holiday rental availability

Holiday Rentals in West Chesterfield

Walk to Mount Snow, Cozy, Clean and Comfortable!

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

Seasons On Mount Snow - Ski-in/Ski-out

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

Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill

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

Cheerful Tiny Cabin hideaway near hiking, skiing & snowmobiling in small town VT

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

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

Dog-friendly chalet cabin with valley view, deck, and private hot tub

Mount Snow's Best View - Sleeps 8-10

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

Wilmington Vacation Rental Near Hiking and Skiing!

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

Green Mountain Modern House: iconic modern getaway

Dog-friendly cabin in the woods with firepit - ski & golf at nearby mountains

Old Ark Retreat | Secluded & spacious dog-friendly home in Wilmington

Waterfront Cottage on Scenic Sportsman Pond

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

Jacksonville Cabin w/ Wraparound Deck & Views

Other types of properties in West Chesterfield you may be interested in

Riverside Hotel, Ascend Hotel Collection

Colonial Motel And Spa

Hampton Inn Brattleboro

Find out more about West Chesterfield

Recent reviews of West Chesterfield properties

Holiday Inn Express Hotel & Suites Brattleboro, an IHG Hotel

Comfort Inn & Suites Brattleboro I-91

Hampton Inn & Suites Keene

Days Inn by Wyndham Keene NH

The Covered Bridge Inn

Fairfield Inn & Suites by Marriott Keene Downtown

Chalet 239

Mount Snow Grand Summit Resort

Hampton Inn Brattleboro

Frequently asked questions