Default HTG hotel image

Chesterfield Holiday 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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Chesterfield holiday rentals

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,206 reviews)
"Friendly hotel staff."
United States
Kathleen
The price is HK$673
HK$927 total
includes taxes & fees
9 Nov - 10 Nov
Berkshire Mountain Lodge
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

2. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (43 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 HK$2,119
HK$3,492 total
includes taxes & fees
15 Oct - 16 Oct
Charming, updated 3 bedroom farmhouse farm stay.
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

3. 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 HK$518
HK$1,937 total
includes taxes & fees
15 Oct - 16 Oct
Modern Studio Ideal for Traveling Professionals
A kitchen with wooden cabinets, a stainless steel dishwasher, and a dining table with benches.

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

A Scenic Townhouse Near Amherst (Next to a Horse Farm)
Sunderland
The price is HK$950
HK$2,420 total
includes taxes & fees
19 Oct - 20 Oct
A Scenic Townhouse Near Amherst (Next to a Horse Farm)
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 HK$753
HK$1,446 total
includes taxes & fees
4 Nov - 5 Nov
2 Twin beds on 1st floor with En-suite bathroom.
Exterior

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

Work, Play & Stay! Apt Near Holyoke Medical Center
Holyoke
10.0 out of 10, Exceptional, (3 reviews)
"Closer to downtown able to"
United States
Jeremy R.
The price is HK$691
HK$2,753 total
includes taxes & fees
15 Oct - 16 Oct
Work, Play & Stay! Apt Near Holyoke Medical Center
A blue house with a porch, a wooden bench, and a door.

7. 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
9.2 out of 10, Wonderful, (10 reviews)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is HK$565
HK$1,701 total
includes taxes & fees
4 Nov - 5 Nov
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A cozy room with two beds, large windows, and a view of a snowy landscape.

8. 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 HK$1,413
HK$2,174 total
includes taxes & fees
2 Nov - 3 Nov
The Creation Station is a cozy place so make yourself at home.
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

9. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
3.0 star property
Holyoke
The price is HK$746
HK$1,905 total
includes taxes & fees
15 Oct - 16 Oct
Modern Studio Ideal for Traveling Professionals
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 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 HK$573
HK$2,490 total
includes taxes & fees
3 Nov - 4 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

11. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is HK$1,144
HK$2,944 total
includes taxes & fees
27 Oct - 28 Oct
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
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 HK$1,916
HK$3,928 total
includes taxes & fees
19 Oct - 20 Oct
Button's Modern Luxury Walkup Downtown Northampton
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

13. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is HK$970
HK$1,724 total
includes taxes & fees
19 Oct - 20 Oct
Private bed with En-suite bathroom Marigold Room
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

14. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (70 reviews)
"It was absolutely amazing Beautiful apartment Clean cozy Beautiful back yard I will definitely stay here again if I am back in this area It’s a 10 out of 10 Thank you David"
United States
Jane P.
The price is HK$982
HK$1,675 total
includes taxes & fees
18 Oct - 19 Oct
Lovely 2nd Floor Apartment
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

15. 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 HK$848
HK$1,552 total
includes taxes & fees
3 Nov - 4 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.

16. 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, (18 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is HK$1,257
HK$3,087 total
includes taxes & fees
28 Oct - 29 Oct
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Room

17. Queen Bedroom in Victorian Home private bath.

Queen Bedroom in Victorian Home private bath.
Shelburne Falls
The price is HK$942
HK$1,692 total
includes taxes & fees
28 Oct - 29 Oct
Queen Bedroom in Victorian Home private bath.
A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

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

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.6 out of 10, Exceptional, (40 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 HK$1,660
HK$3,783 total
includes taxes & fees
19 Oct - 20 Oct
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

19. 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, (34 reviews)
"We were on a girls backpacking trip and this was the perfect location right off the trail to clean up, get some great rest and grab dinner. The people are so friendly in Dalton and this place had everything we needed!"
United States
Allie T.
The price is HK$1,165
HK$2,818 total
includes taxes & fees
15 Oct - 16 Oct
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A bedroom with a bed, dresser, mirror, and a cabinet with glass doors.

20. Penthouse overlooking downtown Amherst!

Penthouse overlooking downtown Amherst!
Amherst
10.0 out of 10, Exceptional, (1 review)
"Great space. Great location."
United States
Mike S.
The price is HK$2,849
HK$5,356 total
includes taxes & fees
27 Oct - 28 Oct
Penthouse overlooking downtown Amherst!
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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"New hotel with clean"
sue 1-night trip
Posted 1 hour ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

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:

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

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

Frequently asked questions

Can I find holiday rentals in Chesterfield?

Yes, there are holiday rentals close to the most popular sights in Chesterfield, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Chesterfield has to offer?

Experience Three Sisters Sanctuary in Goshen, MA: This holiday home rental outside of Chesterfield 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 holiday rental in Chesterfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesterfield. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family getaway.