West Chesterfield Holiday Rentals from €158: Search Short-Term Rentals

Q: What are some of the best holiday rentals that West Chesterfield has to offer?

The Jelly Mill-A Peaceful River Retreat : This holiday home rental outside of West Chesterfield is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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Holiday Rentals in West Chesterfield

"The house was clean, nicely decorated, comfortable and all the amenities we needed! "

"Besides it being a *bit* cold, our stay was great! Very close to Brattleboro and a bunch of other walkable towns. Great hiking areas. The yurt was so cute and had pretty much every cooking supply you could need. Will be back again in warmer weather! :)"

"Very nice, clean, and great area. We enjoyed it very much!"

includes taxes & fees

20 Aug - 21 Aug

"Real Vermont feel. Pretty and nice quiet neighborhood!"

"What an absolutely charming place!! It was so lovely staying here. This place is exactly what we wanted... a little weekend escape not too far from home, nestled in the woods. Absolutely beautiful. The hosts were so kind, too!"

includes taxes & fees

9 Sept - 10 Sept

"really enjoyed our stay. Place would be much better if there was a microwave."

"We enjoyed our stay at the Blue House. Its size and location cannot be beat when it comes to group trips. We will be back!"

"Highly recommend clean beautiful stay!"

includes taxes & fees

25 Aug - 26 Aug

"The place was nice. It was clean, lots of supplies were provided, and it was in a great location. The host contacted me the day before, letting me know that the wifi was out, and the technician was unavailable until the next week. I was appreciative of the heads up. Unfortunately, the TV was unusable without wifi, no option to watch local channels. Cellular (Verizon) data was non-existent throughout the majority of daytime hours. Despite this smallish issue, I would stay here again! "

includes taxes & fees

3 Sept - 4 Sept

"Property was easy to locate. The rooms were perfect! Hot tub was fantastic! "

includes taxes & fees

19 Aug - 20 Aug

"Easy stay, good location for us. Would stay again. "

includes taxes & fees

19 Aug - 20 Aug

Smart TV, fireplace, DVD player, ping pong

"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"

"Wonderful host / fantastic location "

"We had so much fun between swimming and having a fire . The place is beautiful and private and yet not to far from everything."

"The folks are SUPER and made me feel very welome"

includes taxes & fees

8 Sept - 9 Sept

Fridge, microwave, stovetop, coffee/tea maker

"A dream Vt. property, peaceful and scenic, with no worries"

"Had a fantastic weekend at this cabin. Beautifully maintained, sparking clean and beautiful cabin. Everything was exactly as pictured and is even better in person. Would stay here again x100"

"The property was beautiful--great views, super peaceful, and fabulous hosts. "

includes taxes & fees

6 Sept - 7 Sept

"Great house for skiing, within 5 minutes of Mt Snow and the shuttle seems very convenient. The house was great for 8 of us with plenty of room. "

includes taxes & fees

19 Aug - 20 Aug

"Great location to Mt Snow and its surroundings. Easy, pleasant and accommodating communications with the host. Comfortable accommodations. "

includes taxes & fees

19 Aug - 20 Aug

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Top West Chesterfield Hotel Reviews

Comfort Inn & Suites Brattleboro I-91

10/10 Excellent

"Really good staff! "

Riverside Hotel, Ascend Hotel Collection

10/10 Excellent

"The property is beautifully located off the highway yet you feel like you are nestled away a lake front resort. The room was one of the nicest rooms I’ve ever stayed in, reasonably priced and and the property manager was lovely. I would 100% stay there again. "

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 €158 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.

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?

The Jelly Mill-A Peaceful River Retreat: This holiday home rental outside of West Chesterfield is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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, United States Navy Seabee Bridge and Madame Sherris Castle Ruins 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

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Holiday Rentals in West Chesterfield

Black Bear Brook: Historic home minutes from Lake Whitingham and Lake Sadawga.

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

Cozy Updated Log Cabin with Mountain Views close to Monadnock

Beautiful Lodging at Mount Snow with Hot Tub on Deck

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

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!

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

Charming 1-bedroom condo in delightful Dover

Downtown Hot Tub Escape

Lovely 2nd Floor Apartment

Beautiful Custom Built Timber Frame Home, Sleeps 11

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

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

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

Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

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

Family Friendly Hilltop House In Putney Vermont

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Top West Chesterfield Hotel Reviews

Comfort Inn & Suites Brattleboro I-91

The Putney Inn

Colonial Motel And Spa

Best Western Plus Keene Hotel

Latchis Hotel

Keene Elm City Hotel, Ascend Hotel Collection

Riverside Hotel, Ascend Hotel Collection

The Covered Bridge Inn

Travelodge by Wyndham Brattleboro VT

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Frequently asked questions