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Chesterfield Vacation Rentals

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Our top choices for Chesterfield vacation rentals

1. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (41 reviews)
"Great hosts! Very nice and helpful. "
United States
Anonymous traveler
The price is ¥38,698
¥65,984 total
includes taxes & fees
Aug 31 - Sep 1
Charming, updated 3 bedroom farmhouse farm stay.

2. Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (10 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is ¥95,550
¥122,027 total
includes taxes & fees
Aug 16 - Aug 17
Cozy Valley View Post & Beam Villa!

3. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (39 reviews)
"Gorgeous place.Great stay.Will diff be backG"
United States
Gerard C.
The price is ¥35,979
¥79,861 total
includes taxes & fees
Aug 13 - Aug 14
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

4. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,064 reviews)
"Great, spacious accommodation near many things and perfect for Tanglewood concert. Loved the room, the coffee in the lobby, and all the amenities. Would stay again and again"
United States
Andrea
The price is ¥15,067
¥20,388 total
includes taxes & fees
Aug 31 - Sep 1
Berkshire Mountain Lodge

5. The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (77 reviews)
"We had such a great stay at the Creation Station! The host John, showed us around the property and explained how to use everything. He also recommended a great restaurant in town. It was a great experience and would definitely recommend it!"
United States
Paula
The price is ¥28,669
¥44,832 total
includes taxes & fees
Aug 13 - Aug 14
The Creation Station is a cozy place so make yourself at home.

6. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (6 reviews)
"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"
United States
AMY
The price is ¥38,870
¥80,060 total
includes taxes & fees
Aug 17 - Aug 18
Button's Modern Luxury Walkup Downtown Northampton

7. Light-filled treetop apartment close to downtown Greenfield and Highland Park

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
9.8 out of 10, Exceptional, (10 reviews)
"Nice place"
United States
Tom
The price is ¥35,831
¥45,539 total
includes taxes & fees
Sep 10 - Sep 11
Light-filled treetop apartment close to downtown Greenfield and Highland Park

8. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (61 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is ¥18,489
¥32,571 total
includes taxes & fees
Aug 18 - Aug 19
Lovely 2nd Floor Apartment

9. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (30 reviews)
"This was a wonderful place to stay. We especially loved the easy access to the toys so the kids could start playing while we unloaded the car. It was perfect and just what we needed."
United States
Megan A.
The price is ¥23,091
¥54,965 total
includes taxes & fees
Aug 31 - Sep 1
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

10. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (148 reviews)
"Great location"
United States
Will G.
The price is ¥27,235
¥52,357 total
includes taxes & fees
Sep 10 - Sep 11
Big farmhouse in the foothills of the Berkshires

11. Riverbend Berkshire East Basecamp - 3 bedrooms available

Riverbend Berkshire East Basecamp - 3 bedrooms available
Charlemont
10.0 out of 10, Exceptional, (5 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is ¥33,168
¥75,636 total
includes taxes & fees
Aug 28 - Aug 29
Riverbend Berkshire East Basecamp - 3 bedrooms available

12. Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (16 reviews)
"Comfortable stay"
United States
Nicholas B.
The price is ¥40,853
¥81,945 total
includes taxes & fees
Aug 17 - Aug 18
Townhouse with Pool Table - Renovated w/ King Bed

13. Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3.0 star property
Holyoke
The price is ¥16,723
¥40,443 total
includes taxes & fees
Aug 16 - Aug 17
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

14. Chef's Kitchen Family Basecamp Amherst

Chef's Kitchen Family Basecamp Amherst
3.0 star property
East Village Historic District
The price is ¥57,972
¥107,981 total
includes taxes & fees
Aug 13 - Aug 14
Chef's Kitchen Family Basecamp Amherst

15. Spacious & Cozy Ground Floor 2/3 Bed private suite

Spacious & Cozy Ground Floor 2/3 Bed private suite
Shelburne Falls
9.6 out of 10, Exceptional, (5 reviews)
"Wonderful property with an exceptional host!"
United States
Russ D.
The price is ¥36,027
¥71,375 total
includes taxes & fees
Sep 8 - Sep 9
Spacious & Cozy Ground Floor 2/3 Bed private suite

16. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (53 reviews)
"Our 4th week here and our crew could not be happier with the accommodations"
United States
Maureen A.
Spacious 5BR w/ Hot Tub & Games

17. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (6 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ¥27,235
¥65,291 total
includes taxes & fees
Sep 9 - Sep 10
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

18. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ¥27,522
¥65,611 total
includes taxes & fees
Aug 25 - Aug 26
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

19. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
The price is ¥25,639
¥58,169 total
includes taxes & fees
Sep 9 - Sep 10
Cozy private 2 bed apartment in Shelburne Falls

20. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
The price is ¥18,157
¥33,269 total
includes taxes & fees
Aug 24 - Aug 25
Balcony Room in Victorian Home private bath
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.
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Top Chesterfield Hotel Reviews

Find out more about Chesterfield

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

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Frequently asked questions

Can I find vacation rentals in Chesterfield?

Yes, we have vacation rentals near popular attractions in Chesterfield, or you can go with a secluded option if you want a relaxing place to stay. Chesterfield is known for its restaurants and shopping. Make sure you have time to check out the parks while you're in the area.

What are some of the best vacation rentals in Chesterfield?

Experience Three Sisters Sanctuary in Goshen, MA: You might want to consider this vacation home rental near Chesterfield, which is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

What’s there to see and do in Chesterfield?

Chesterfield Gorge and Westfield River are a couple of lovely local spots to get outside and enjoy nature. Chesterfield Public Library and Chesterfield Town Hall are other places to visit while you're in town.

What’s a vacation rental in Chesterfield like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Chesterfield. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family trip or a small group gathering.