Default HTG hotel image

Chesterfield Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Chesterfield vacation rentals

Property grounds

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 SAR 912
SAR 1,556 total
includes taxes & fees
31 Aug - 1 Sep
Charming, updated 3 bedroom farmhouse farm stay.
Property grounds

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 SAR 2,253
SAR 2,877 total
includes taxes & fees
16 Aug - 17 Aug
Cozy Valley View Post & Beam Villa!
Property grounds

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 SAR 993
SAR 2,066 total
includes taxes & fees
19 Aug - 20 Aug
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Lobby

4. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,069 reviews)
"A beautiful, spacious and conveniently located suite just a few minutes away that everything the Berkshires have to offer. I really love this place!"
United States
Karilyn
The price is SAR 355
SAR 481 total
includes taxes & fees
31 Aug - 1 Sep
Berkshire Mountain Lodge
Desk, iron/ironing board, travel crib, WiFi

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 SAR 676
SAR 1,023 total
includes taxes & fees
31 Aug - 1 Sep
The Creation Station is a cozy place so make yourself at home.
Interior

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 SAR 916
SAR 1,888 total
includes taxes & fees
17 Aug - 18 Aug
Button's Modern Luxury Walkup Downtown Northampton
Exterior

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 SAR 845
SAR 1,078 total
includes taxes & fees
16 Aug - 17 Aug
Light-filled treetop apartment close to downtown Greenfield and Highland Park
Interior

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 SAR 436
SAR 768 total
includes taxes & fees
17 Aug - 18 Aug
Lovely 2nd Floor Apartment
Coffee/tea maker, fridge, microwave, oven

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 SAR 544
SAR 1,296 total
includes taxes & fees
31 Aug - 1 Sep
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Property grounds

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 SAR 713
SAR 1,337 total
includes taxes & fees
23 Aug - 24 Aug
Big farmhouse in the foothills of the Berkshires
Property grounds

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 SAR 782
SAR 1,783 total
includes taxes & fees
28 Aug - 29 Aug
Riverbend Berkshire East Basecamp - 3 bedrooms available
3 bedrooms, desk, iron/ironing board, travel crib

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 SAR 963
SAR 1,932 total
includes taxes & fees
17 Aug - 18 Aug
Townhouse with Pool Table - Renovated w/ King Bed
Apartment (0 Bedroom) | Interior

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 SAR 330
SAR 882 total
includes taxes & fees
27 Aug - 28 Aug
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
House, 4 Bedrooms | Interior

14. Chef's Kitchen Family Basecamp Amherst

Chef's Kitchen Family Basecamp Amherst
3.0 star property
East Village Historic District
The price is SAR 1,367
SAR 2,546 total
includes taxes & fees
16 Aug - 17 Aug
Chef's Kitchen Family Basecamp Amherst
Living area

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 SAR 854
SAR 1,688 total
includes taxes & fees
8 Sep - 9 Sep
Spacious & Cozy Ground Floor 2/3 Bed private suite
Coffee/tea maker, fridge, microwave, oven

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.
The price is SAR 1,256
SAR 2,682 total
includes taxes & fees
16 Aug - 17 Aug
Spacious 5BR w/ Hot Tub & Games
Interior

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 SAR 638
SAR 1,535 total
includes taxes & fees
9 Sep - 10 Sep
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Outdoor spa tub

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 SAR 645
SAR 1,543 total
includes taxes & fees
19 Aug - 20 Aug
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Iron/ironing board, WiFi, bed sheets

19. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
The price is SAR 604
SAR 1,371 total
includes taxes & fees
24 Aug - 25 Aug
Cozy private 2 bed apartment in Shelburne Falls
1 bedroom, desk, iron/ironing board, WiFi

20. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
The price is SAR 428
SAR 784 total
includes taxes & fees
24 Aug - 25 Aug
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Suite was beautiful with plenty of room. Kitchen was well stocked with anything you might need. My only caution is to be careful when you step into the tub. It was slippery!"
Deborah 1-night trip
Posted 1 hour ago
Berkshire Mountain Lodge

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.