West Chesterfield Holiday Rentals: Short-Term Accommodations for Rent

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.

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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!"

HK$2,106 total

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!"

HK$1,706 total

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!"

HK$2,034 total

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! "

HK$1,583 total

includes taxes & fees

3 Sept - 4 Sept

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

HK$3,803 total

includes taxes & fees

19 Aug - 20 Aug

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

HK$1,409 total

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"

HK$1,910 total

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. "

HK$2,244 total

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. "

HK$6,777 total

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. "

HK$3,422 total

includes taxes & fees

19 Aug - 20 Aug

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top West Chesterfield Hotel Reviews

Best Western Plus Keene Hotel

10/10 Excellent

"Clean, comfortable room, great breakfast & friendly 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. "

Valley Craft Ales

10/10 Excellent

"After walking around the quaint town of Wilmington, we couldn't decide where to go for dinner. We went to the bar to taste test the beer and ended up ordering a pizza. The bartender gave us ice to take upstairs. The building is an older building and has many eccentricities. We loved staying here and will stay again if in the neighborhood."

Hampton Inn Brattleboro

10/10 Excellent

"Hotel Review: Hampton Inn – A Seamless Stay with Exceptional Service I recently stayed at the Hampton Inn and was thoroughly impressed by the level of service and hospitality from start to finish. From the moment I walked in, the front desk staff made me feel genuinely welcome. Check-in was quick, and they even offered complimentary bottled water and local dining recommendations, which was a thoughtful touch. The room was spotless, well-stocked, and comfortable — exactly what you’d hope for after a long day of travel. The housekeeping team clearly takes pride in their work. I also appreciated the small details, like plenty of charging ports, crisp bedding, and a quiet HVAC system. What truly stood out, though, was the service. Every staff member I interacted with was friendly, helpful, and professional. Whether it was a late-night request for extra towels or early morning coffee in the lobby, they handled everything with a smile and prompt attention. Breakfast was fresh and well-organized, with a good mix of hot and cold options. The dining area was clean and constantly replenished, even during peak hours — another example of the staff going above and beyond. Overall, this Hampton Inn exceeded expectations. It’s a great value with top-tier customer service that rivals more expensive hotels. I wouldn’t hesitate to stay here again or recommend it to anyone traveling through the area."

Find out more about West Chesterfield

Search for holiday rentals in West Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in West Chesterfield using one of the methods below:

View our selection of featured holiday rentals in West Chesterfield
Use the map to find apartments and other holiday homes in the West Chesterfield neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in West Chesterfield while they last

Look no further and take a look at our great range of rental properties in West Chesterfield!

Explore a world of travel with Expedia

All accommodation types in West Chesterfield

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.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

West Chesterfield Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

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

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

Valley Craft Ales

Hampton Inn Brattleboro

Comfort Inn & Suites Brattleboro I-91

Find out more about West Chesterfield

Explore a world of travel with Expedia

Frequently asked questions