West Chesterfield Vacation Rentals from $134: Search Short-Term Rentals

Q: What's the top vacation rental that West Chesterfield has to offer?

Family Friendly Hilltop House In Putney Vermont : Visitors like this West Chesterfield vacation home rental. It is located on a lake and has a balcony, a selection of games, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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Our top choices for West Chesterfield vacation rentals

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

Hinsdale

Adrienne

$145 nightly

Aug 24 - Aug 25

Total with taxes and fees

2. Family Friendly Hilltop House In Putney Vermont

Putney

Susan O.

$286 nightly

Sep 1 - Sep 2

Total with taxes and fees

3. Yurt Oasis in the woods of Hinsdale, NH

Hinsdale

Julie

$124 nightly

Aug 24 - Aug 25

Total with taxes and fees

4. Chalet Mount Snow/Stratton Skiing/hiking

East Dover

Roy-michael G.

$406 nightly

Aug 30 - Aug 31

Total with taxes and fees

5. 2 private mountain RV pads for rent. Full hook ups

Winchester

$75 nightly

Aug 15 - Aug 16

Total with taxes and fees

6. Lovely 2nd Floor Apartment

Greenfield

Christa B.

$183 nightly

Aug 16 - Aug 17

Total with taxes and fees

7. The Studio with a View. Bring your dog, too!

Brattleboro

s p.

$221 nightly

Sep 2 - Sep 3

Total with taxes and fees

8. Stunning Glass House nestled in the Vermont wilderness!

Guilford

Chris O.

$396 nightly

Sep 7 - Sep 8

Total with taxes and fees

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Top West Chesterfield Hotel Reviews

Hampton Inn Brattleboro

10/10 Excellent

"Too tired to think about it. Sorry."

Inn At Mount Snow

10/10 Excellent

"This was such a delightful treat. The property is renovated and every room is beautifully decorated yet unique. The common areas are beautiful and offer every small detail you could want. From fresh cookies, s'mores kits, bonfire kits, board games and a record player with plenty of musical choices. This property offers free breakfast daily. The breakfast was delicious with fresh granola, muffins, cereal, fruit, and yogurt. The innkeepers are friendly and helpful. They live on the property and are available if you need anything. The views from the property are spectacular. I would highly recommend this property and look forward to staying here again."

Windmill Motel Restaurant

10/10 Excellent

"I love the outdoor seating area with the tent and outdoor couches and I love the colors and textures used for the room I stayed in. When I checked in, I was hot from being at SoulFest and the owners gave me a cloth hand fan for free! When I came home that night, I was hungry and there were chips and chocolates in my room! That was wonderful and thoughtful. They also sell food in the office, if you need something more substantial. The mattress and pillows were so comfortable that I had trouble getting myself up the next morning! Slept like a rock. 10/10 for the Windmill! Can't wait to see what the restaurant will be like when it opens! I will definitely come back next year, if there is availability!"

Latchis Hotel

8/10 Good

"In an old Theater building. Definitely has character and cool features. We arrived too late for the movies, but still fun. In central Brattleboro which has some interesting shops, but is suffering from homelessnes and mental illness/drug use. Didnt really feel unsafe and we walked a few blocks to a fun restaurant with good food & karioke. Person at desk was lovely and helpful. Room was ok- a little dated and could be cleaner."

Find out more about West Chesterfield

Everything you need to know about West Chesterfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the West Chesterfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

West Chesterfield vacation 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 low season months. For more hustle and bustle, you may prefer to visit West Chesterfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $134 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on West Chesterfield rentals

At Expedia, we put the best West Chesterfield vacation 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 vacation.

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 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?

Family Friendly Hilltop House In Putney Vermont: Visitors like this West Chesterfield vacation home rental. It is located on a lake and has a balcony, a selection of games, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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, Wantastiquet Mountain and Connecticut River 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.

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Our top choices for West Chesterfield vacation rentals

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

2. Family Friendly Hilltop House In Putney Vermont

3. Yurt Oasis in the woods of Hinsdale, NH

4. Chalet Mount Snow/Stratton Skiing/hiking

5. 2 private mountain RV pads for rent. Full hook ups

6. Lovely 2nd Floor Apartment

7. The Studio with a View. Bring your dog, too!

8. Stunning Glass House nestled in the Vermont wilderness!

9. 2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

10. Cozy 3 bedroom Cottage on Farm with great outdoor space 10 min to Bellows Falls

11. Cozy 3 bedroom condo 2.5 miles to Mount Snow

12. Vikings Villages Resort - Double Bed Room

13. Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

14. Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

15. Large Farmhouse with expansive views, firepit 15 min north of Keene

16. 4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

17. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

18. Family-Friendly 3BR Historic Home – Walk to Keene Central Square & Trails!

19. Cozy Studio | Ski-In Access + Kitchenette

20. Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Find vacation rentals that suit your style

Top West Chesterfield Hotel Reviews

Hampton Inn Brattleboro

Inn At Mount Snow

Hideaway Inn Mt. Snow

Best Western Plus Keene Hotel

Vikings Villages Resort

Riverside Hotel, an Ascend Collection Hotel

Windmill Motel Restaurant

Latchis Hotel

The Putney Inn

Find out more about West Chesterfield

Frequently asked questions

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