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Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Chesterfield apartments

A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

1. 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 CA $129
CA $239 total
includes taxes & fees
Nov 19 - Nov 20
2 Twin beds on 1st floor with En-suite bathroom.
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

2. 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 CA $80
CA $317 total
includes taxes & fees
Nov 19 - Nov 20
Modern Studio Ideal for Traveling Professionals
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
3.0 star property
Holyoke
The price is CA $120
CA $325 total
includes taxes & fees
Nov 19 - Nov 20
Modern Studio Ideal for Traveling Professionals
A modern fireplace with a glass enclosure, decorative items, and a sign that reads 'blessed.'

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 CA $174
CA $411 total
includes taxes & fees
Nov 9 - Nov 10
A Scenic Townhouse Near Amherst (Next to a Horse Farm)
A blue house with a porch, a wooden bench, and a door.

5. 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 CA $125
CA $321 total
includes taxes & fees
Nov 9 - Nov 10
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
A modern kitchen with a central island, bar stools, and a bicycle.

6. 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 CA $342
CA $670 total
includes taxes & fees
Nov 17 - Nov 18
Button's Modern Luxury Walkup Downtown Northampton
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

7. 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 CA $157
CA $421 total
includes taxes & fees
Nov 10 - Nov 11
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

8. Balcony Room in Victorian Home private bath

Balcony Room in Victorian Home private bath
Shelburne Falls
The price is CA $153
CA $269 total
includes taxes & fees
Nov 16 - Nov 17
Balcony Room in Victorian Home private bath
A living room with a beige sofa, a patterned rug, and a wooden floor.

9. 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 CA $225
CA $485 total
includes taxes & fees
Nov 15 - Nov 16
Spacious & Cozy Ground Floor 2/3 Bed private suite
A living room with a fireplace, a sofa, a coffee table, and a TV.

10. Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (13 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is CA $217
CA $299 total
includes taxes & fees
Nov 10 - Nov 11
Cozy 2-bedroom apartment in Chicopee
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

11. 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 CA $145
CA $258 total
includes taxes & fees
Nov 15 - Nov 16
Rose room Victorian home queen bed private bath
A house with a staircase leading to a porch, surrounded by snow and string lights.

12. 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, (13 reviews)
"Nice place"
United States
Tom
The price is CA $181
CA $221 total
includes taxes & fees
Nov 7 - Nov 8
Light-filled treetop apartment close to downtown Greenfield and Highland Park
A living room with a sofa set, a coffee table, and two lamps.

13. Cozy First Floor Apartment. Located in a quiet neighborhood.

Cozy First Floor Apartment. Located in a quiet neighborhood.
Chicopee
9.6 out of 10, Exceptional, (14 reviews)
"Check in was very easy. The apartment had all the necessities in the kitchen and bathroom. Location was convenient and the neighborhood very safe/quiet."
United States
Morrris
The price is CA $250
CA $430 total
includes taxes & fees
Nov 30 - Dec 1
Cozy First Floor Apartment. Located in a quiet neighborhood.
A modern living room with a sofa, a coffee table, and a fireplace.

14. A Cozy Condo Near Horse Farm + Mount Sugarloaf

A Cozy Condo Near Horse Farm + Mount Sugarloaf
Sunderland
The price is CA $302
CA $591 total
includes taxes & fees
Nov 8 - Nov 9
A Cozy Condo Near Horse Farm + Mount Sugarloaf
A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.

15. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (19 reviews)
"Our stay was beautiful! The check in process was super easy and the building was easy to access. The apartment was very clean and it was a lovely stay."
United States
Margaret C.
The price is CA $203
CA $373 total
includes taxes & fees
Nov 7 - Nov 8
Penthouse Apartment on Park Street
A modern kitchen with a dining area, built-in shelves, and a large window.

16. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Lenox
The price is CA $314
CA $425 total
includes taxes & fees
Nov 7 - Nov 8
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
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 reviews in Chesterfield

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

We stayed 5 days in the ground floor coach house room which was a lovely, large room with a sitting and dinning area as well as a private patio area. The room was lovely, AC worked great on an extremely hot week and the breakfast, all days snacks and common area were great as well. The staff was helpful with tips about things to do in the area. We had a great visit.
Canada
Graham
Reviewed July 5, 2026
The Ellery

Frequently Asked Questions

What's it like to stay at an apartment in Chesterfield?

You might not have many choices within the heart of Chesterfield, but Expedia can help you locate accommodations within the larger area with similar amenities to an apartment. When you search for a place to stay on Expedia, you can use the filters to search for conveniences you might find in an apartment like a kitchen. You can also filter by similar property types like vacation homes, condos, or guest houses.

Why choose an apartment over a traditional hotel room?

Often offering more space than a traditional hotel room, an apartment includes a kitchen for convenient home-cooked meals. Apartments are ideal for families who want the conveniences of home but also for solo travelers who want to stay in at night and plan out their next day.

What's the top apartment I should consider for a stay in Chesterfield?

Below are some of the favorite apartments in the area to choose from: Quiet Neighborhood, For Bird Lovers: Located 13.2 mi/21.3 km away in South Deerfield. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires: Located in Greenfield, 18.5 mi/29.8 km from Chesterfield. Includes private patios and Smart TVs. Access to onsite laundry facilities is available on site.

What will the weather be like when I travel to Chesterfield?

Though weather is just one factor, it can really affect your travel plans, especially if you are planning a longer stay in Chesterfield. The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Chesterfield are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.

What are the must-see places to visit in Chesterfield?

Chesterfield Gorge and Chesterfield Gorge Reservation are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Chesterfield Public Library and Chesterfield Town Hall.

What's the best way to get to and around Chesterfield?

Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Westfield, MA (BAF-Barnes Municipal), which is located 16.6 mi (26.8 km) from the heart of the city. You can also search for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 23.2 mi (37.3 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.

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