Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Chesterfield vacation rentals

A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

1. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (44 reviews)
"Wonderful place to stay with our two teens. We visited family in Amherst, looked at colleges and had a great time touring historic sites. Definitely recommend!"
United States
Nancy M.
The price is SAR 926
SAR 1,490 total
includes taxes & fees
6 Dec - 7 Dec
Charming, updated 3 bedroom farmhouse farm stay.
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,271 reviews)
"Excellent stay!!!!"
United States
Susan J
The price is SAR 288
SAR 406 total
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
A spacious living room with a wooden staircase, a dining area, and a television.

3. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is SAR 225
SAR 1,061 total
includes taxes & fees
18 Nov - 19 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

4. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"The room was very clean and modern. The check-in process was easy and I had the best rest that I had in a long time. Being in the lower level with no windows provided a very quiet and dark ambiance at night. There is ample lighting throughout the unit if needed though, you can really unplug here. I would definitely stay here again"
United States
Kebreab H.
The price is SAR 214
SAR 847 total
includes taxes & fees
16 Nov - 17 Nov
Modern Studio Ideal for Traveling Professionals
A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

5. 2 Twin beds on 1st floor with En-suite bathroom.

2 Twin beds on 1st floor with En-suite bathroom.
Shelburne Falls
The price is SAR 345
SAR 641 total
includes taxes & fees
15 Nov - 16 Nov
2 Twin beds on 1st floor with En-suite bathroom.
A two-story residential building with a sign indicating 'Victory Residence' and the address '1785'.

6. Work, Play & Stay! Apt Near Holyoke Medical Center

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful apartment! Amazing finishes, well appointed, pristine apartment in Holyoke. Great communication from the host. A quick trip to Dam Coffee Shop for great coffee and breakfast options. Not too far from Stop & Shop for food and short ride to highway. Would book this spot again."
United States
Yvonne A.
The price is SAR 214
SAR 1,082 total
includes taxes & fees
22 Nov - 23 Nov
Work, Play & Stay! Apt Near Holyoke Medical Center
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

7. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
3.0 star property
Holyoke
The price is SAR 323
SAR 873 total
includes taxes & fees
16 Nov - 17 Nov
Modern Studio Ideal for Traveling Professionals
A blue house with a porch, a wooden bench, and a door.

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

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.4 out of 10, Exceptional, (11 reviews)
"Very satisfied with the stay . Clean quiet and relaxing stay."
United States
JAMES S.
The price is SAR 372
SAR 901 total
includes taxes & fees
14 Dec - 15 Dec
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A modern fireplace with a glass enclosure, decorative items, and a sign that reads 'blessed.'

9. A Scenic Townhouse Near Amherst (Next to a Horse Farm)

A Scenic Townhouse Near Amherst (Next to a Horse Farm)
Sunderland
10.0 out of 10, Exceptional, (1 review)
"Great place! Very clean!"
United States
Sherry T.
A Scenic Townhouse Near Amherst (Next to a Horse Farm)
A dining room with a wooden table, chairs, a fireplace, a bookcase, and a stained glass ceiling light.

10. Private room with En-suite bathroom Marigold Room

Private room with En-suite bathroom Marigold Room
Shelburne Falls
Private room with En-suite bathroom Marigold Room
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

11. 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, (41 reviews)
"The house was very clean! The hot tub was great! From checking in and checking out the host made everything so easy. We will definitely stay again!"
United States
Kyle R.
The price is SAR 696
SAR 1,616 total
includes taxes & fees
16 Nov - 17 Nov
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A modern kitchen with a central island, bar stools, and a bicycle.

12. Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (8 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 1,786 total
includes taxes & fees
17 Nov - 18 Nov
Button's Modern Luxury Walkup Downtown Northampton
A hot tub on a wooden deck with snow on the ground and trees in the background.

13. 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, (79 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 998 total
includes taxes & fees
18 Nov - 19 Nov
The Creation Station is a cozy place so make yourself at home.
A television displaying a coastal scene, a window with a view of buildings, and a sign reading 'CAPE COD'.

14. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
10.0 out of 10, Exceptional, (2 reviews)
"Great space. Great location."
United States
Mike S.
The price is SAR 1,032
SAR 2,033 total
includes taxes & fees
15 Nov - 16 Nov
Penthouse overlooking downtown Amherst!
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

15. 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, (35 reviews)
"Very smooth process for check in and directions. Well provisioned, super clean rooms. Really enjoyed learning about Dalton. And so many sights nearby we love!"
United States
Marcia O.
The price is SAR 646
SAR 1,400 total
includes taxes & fees
14 Dec - 15 Dec
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A dining room with a wooden table and chairs, a fireplace, a bookshelf, and a stained glass ceiling light.

16. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
Balcony Room in Victorian Home private bath
A triangular-shaped building with a balcony and a wooden picnic table in front.

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, (10 reviews)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
United States
Brian C.
The price is SAR 547
SAR 1,349 total
includes taxes & fees
16 Nov - 17 Nov
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A dining room with a wooden table and chairs, a fireplace, a bookshelf, and a stained glass ceiling light.

18. Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
8.0 out of 10, Very good, (1 review)
"Very cute and welcoming B&B guest house. It was not clear to me that our private bathroom was across the hall. Some are and some not so check for that."
United States
Mikaela M.
The price is SAR 388
SAR 690 total
includes taxes & fees
15 Nov - 16 Nov
Rose room Victorian home queen bed private bath
A hot tub with a string of lights above it, set against a dark night sky.

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is SAR 601
SAR 1,355 total
includes taxes & fees
16 Nov - 17 Nov
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A spacious dining area with a wooden table, chairs, and a potted plant.

20. Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (13 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is SAR 1,877
SAR 2,276 total
includes taxes & fees
18 Nov - 19 Nov
Cozy Valley View Post & Beam Villa!
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

A brick building with a green door, white porch chairs, and a pathway lined with pink flowers.
The Ellery

The Ellery

The Ellery
Northampton

10/10 Excellent

It’s a great place to stay and we like the breakfast!
United States
Marilyn
Reviewed June 14, 2025
The Ellery

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: Visitors like this Chesterfield vacation home rental. It 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 Chesterfield Gorge Reservation 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.