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Check prices for these dates

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2 Jan - 4 Jan
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23 Jan - 25 Jan
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20 Feb - 22 Feb

Our top choices for Chesterfield apartments

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

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
9.0 out of 10, Wonderful, (4)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is €180
includes taxes & fees
26 Dec - 27 Dec
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
TV
Charming Chicopee Getaway

Charming Chicopee Getaway

Charming Chicopee Getaway
Chicopee
7.6 out of 10, Good, (4)
"We really appreciated the stay to get together with family. There was plenty of space to play with the toddler and set up the pack-n-play for the infant. And then plenty of room to play board games after the babies were put to bed. "
United States
Tamara S.
The price is €228
includes taxes & fees
12 Jan - 13 Jan 2026
Charming Chicopee Getaway
WiFi, bed sheets
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse
Lanesborough
9.6 out of 10, Exceptional, (67)
"We had a lovely stay! The studio was comfortable, clean, and just what we needed. Our hosts were friendly and helpful!"
United States
Janice L.
The price is €180
includes taxes & fees
24 Dec - 25 Dec
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Exterior
2 Twin beds on 1st floor with En-suite bathroom.

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 €132
includes taxes & fees
7 Jan - 8 Jan 2026
2 Twin beds on 1st floor with En-suite bathroom.
Living area
Penthouse Apartment on Park Street

Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
2.0 star property
Adams
9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is €213
includes taxes & fees
2 Jan - 3 Jan 2026
Penthouse Apartment on Park Street
Living area
Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (2)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is €178
includes taxes & fees
7 Jan - 8 Jan 2026
Cozy 2-bedroom apartment in Chicopee
Terrace/patio
Terrific 3-bedroom unit in charming Leverett with AC

Terrific 3-bedroom unit in charming Leverett with AC

Terrific 3-bedroom unit in charming Leverett with AC
Leverett
10.0 out of 10, Exceptional, (1)
"The apartment is lovely, so comfortable and quiet!! Caitlin was a wonderful host, very responsive. Would absolutely stay again! "
United States
Anna B.
The price is €412
includes taxes & fees
24 Dec - 25 Dec
Terrific 3-bedroom unit in charming Leverett with AC
Fridge, microwave, oven, stovetop
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Amherst
9.2 out of 10, Wonderful, (19)
"Great property! Thank you for a wonderful stay."
United States
David
The price is €365
includes taxes & fees
30 Dec - 31 Dec
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Interior
Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (2)
"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 €525
includes taxes & fees
5 Jan - 6 Jan 2026
Button's Modern Luxury Walkup Downtown Northampton
Dining
Humble home with free breakfast

Humble home with free breakfast

Humble home with free breakfast
Chicopee
5.4 out of 10, (3)
"This host cancelled my booking 3 hours after our check in time. We had already arrived and were left stranded with no where to stay."
United States
Kathleen D.
The price is €249
includes taxes & fees
19 Jan - 20 Jan 2026
Humble home with free breakfast
Dining
Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse
Lanesborough
9.4 out of 10, Exceptional, (40)
"It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host."
United States
Roy
The price is €181
includes taxes & fees
4 Jan - 5 Jan 2026
Charming Apt in 18th c Berkshire Farmhouse
Exterior
Rose wisteria 4 guests 2 bedrooms-full+queen beds

Rose wisteria 4 guests 2 bedrooms-full+queen beds

Rose wisteria 4 guests 2 bedrooms-full+queen beds
Shelburne Falls
The price is €186
includes taxes & fees
6 Jan - 7 Jan 2026
Rose wisteria 4 guests 2 bedrooms-full+queen beds
Dining
Bright Boho Apt in 18th c Berkshire Farmhouse

Bright Boho Apt in 18th c Berkshire Farmhouse

Bright Boho Apt in 18th c Berkshire Farmhouse
Lanesborough
9.0 out of 10, Wonderful, (22)
"I loved staying here the weekend with my friends, the owner Patrick was so accommodating and helpful!"
United States
Mckenna d.
The price is €192
includes taxes & fees
4 Jan - 5 Jan 2026
Bright Boho Apt in 18th c Berkshire Farmhouse
Smart TV
Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Chic corporate apartment in wonderful Pittsfield with AC, WiFi
2.0 star property
Pittsfield
2.0 out of 10, (1)
"THIS. PLACE. IS. A. DUMP. Do NOT STAY HERE under any circumstances."
United States
Michael
The price is €178
includes taxes & fees
24 Dec - 25 Dec
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"While waiting for our vallet car due to construction. The hotel staff were engaging and had personal conversations with us. Rooms were good and all staff treated us exceptional. Give them an atta boy on proformance"
Nathan 1-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about Chesterfield

Chesterfield Apartments information

Number of reviews
168
Accommodation
61 Apartments
Lowest Price
€132
Highest Price
€525

Frequently asked questions

What's it like to stay at an apartment in Chesterfield?
There might not be many choices within the heart of Chesterfield, but Expedia can help you search for accommodation in the area similar to apartments. When you search for a place to stay on Expedia, you can use the filters to search for a kitchen— one of the conveniences often found in an apartment. You can even filter by similar property types like holiday homes, condos or cabins.
Why would you choose an apartment versus a traditional hotel?
Often more spacious than a traditional hotel room, an apartment comes with a kitchen, so you can cook some of your meals. Apartments are ideal for families who want the conveniences of home, and also for couples looking for something with a more local feel.
What's the best apartment I should consider for a stay in Chesterfield?
Below are some of the favourite apartments in the area to choose from: Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!: Located in Amherst , 16.5 mi/26.5 km from the heart of Chesterfield. Includes a Smart TV . Access to on-site laundry facilities is available on site . Elm Suite with a Private Bathroom in front of Smith College Quadrangle: Located 11.2 mi/18.1 km away in Northampton . Amenities include in-room jetted baths . Access to 1 hot tub is available on site . Comfort, luxury, privacy: It's situated in Amherst , 17 mi/27.3 km away. Includes a Smart TV . Charming Apt in 18th c Berkshire Farmhouse: Located in Lanesborough , 22.3 mi/35.9 km from Chesterfield. Includes a fireplace . Access to on-site laundry facilities is available on site .
What will the weather be like during my trip to Chesterfield?
Although 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 temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Chesterfield are January, February, November and March, with each month seeing an average of 16 cm 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 make your trip smoother when you get to your destination. Fly into Westfield, MA (BAF-Barnes Municipal), which is located 16.6 mi (26.8 km) away. 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, consider renting a car to explore more sights.

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