Photo by Elizabeth Massa Peroulakis

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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 71 Apartments in Chester with updated reviews, rates, and availability.

51 Church Street, Lenox MA - One Bedroom Unit
Fridge, microwave, oven, stovetop

51 Church Street, Lenox MA - One Bedroom Unit

10.0 out of 10, Exceptional, (27)
"Clean, comfortable and great location."
51 Church Street, Lenox MA - One Bedroom Unit
Easthampton Apartment Near Breweries & Rail Trail!
Interior

Easthampton Apartment Near Breweries & Rail Trail!

9.8 out of 10, Exceptional, (13)
"Clean unit, comfy beds, plentiful soft towels. Good location for our visit with family, plenty of parking."
Easthampton Apartment Near Breweries & Rail Trail!
Bright Springfield Apartment w/ 2 Balconies!
Property grounds

Bright Springfield Apartment w/ 2 Balconies!

9.4 out of 10, Exceptional, (10)
"Excellent communication, easy in and out."
Bright Springfield Apartment w/ 2 Balconies!
Elm Suite with a Private Bathroom in front of Smith College Quadrangle
1 bedroom, WiFi

Elm Suite with a Private Bathroom in front of Smith College Quadrangle

9.8 out of 10, Exceptional, (16)
"Good location"
Elm Suite with a Private Bathroom in front of Smith College Quadrangle
Low-scent, historic downtown gem with sustainability practices throughout.
Outdoor dining

Low-scent, historic downtown gem with sustainability practices throughout.

10.0 out of 10, Exceptional, (6)
"Great property and communication!"
Low-scent, historic downtown gem with sustainability practices throughout.
Birch Suite- 2nd Floor Apartment with Kitchenette in front of Smith College
Exterior

Birch Suite- 2nd Floor Apartment with Kitchenette in front of Smith College

10.0 out of 10, Exceptional, (12)
"what an adorable little apartment! it was clean, cozy, decorated with taste and located very conveniently. communication with xianxiu was easy and friendly. i will definitely try to stay here again the next time I visit!"
Birch Suite- 2nd Floor Apartment with Kitchenette in front of Smith College
Maple Suite- Private Ground Floor Apartment in front of Smith College
Interior

Maple Suite- Private Ground Floor Apartment in front of Smith College

9.8 out of 10, Exceptional, (15)
"Lovely, quaint place that was just what we were looking for. "
Maple Suite- Private Ground Floor Apartment in front of Smith College
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
Living area

Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge

2.0 star property
10.0 out of 10, Exceptional, (5)
"Very clean and nicely decorated apartment in center of town. Great location. Really enjoyed our vacation."
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
Easthampton Vacation Rental - Walk to Breweries!
2 bedrooms, iron/ironing board, internet, bed sheets

Easthampton Vacation Rental - Walk to Breweries!

9.6 out of 10, Exceptional, (13)
"It was a perfect location close to our family. The place was clean and instructions clear. Definitely will be back"
Easthampton Vacation Rental - Walk to Breweries!
The Studio mini home away from home in the Berkshires
Outdoor dining

The Studio mini home away from home in the Berkshires

9.6 out of 10, Exceptional, (28)
"Zero complaints. Perfect location"
The Studio mini home away from home in the Berkshires
Charming Apt in 18th c Berkshire Farmhouse
Miscellaneous

Charming Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (31)
"The property was perfect for us !! Lots of room and the beds are very comfortable. "
The price is AED 496
AED 758 total
includes taxes & fees
11 May - 12 May
Charming Apt in 18th c Berkshire Farmhouse
Upstairs on Main with private bathroom
Property grounds

Upstairs on Main with private bathroom

9.2 out of 10, Wonderful, (32)
"The place is as described. Excellent location."
Upstairs on Main with private bathroom
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Living area

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

2.0 star property
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Golf

1500 sqft private entrance with beautiful views of the Berkshire Mountains

10.0 out of 10, Exceptional, (41)
"Perfect get away, convenient to everything."
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Terrace/patio

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (61)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Heart of Lenox!! - renovated downtown apartment
Flat-screen TV

Heart of Lenox!! - renovated downtown apartment

10.0 out of 10, Exceptional, (68)
"Unbeatable location, charming and well-appointed apartment, super comfortable beds, easy communication with host. We will be back! "
Heart of Lenox!! - renovated downtown apartment
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Miscellaneous

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (62)
"Great value, so much better than all the touristy motels in the area!"
The price is AED 496
AED 758 total
includes taxes & fees
11 May - 12 May
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Gateway to the Berkshires - Renovated downtown apartment
Exterior

Gateway to the Berkshires - Renovated downtown apartment

10.0 out of 10, Exceptional, (7)
"Emmy is a great hostess. The apartment is nicely appointed and in a great location to restaurants and shops and attractions in the Berkshires. "
Gateway to the Berkshires - Renovated downtown apartment
Charming Chicopee Getaway
Fridge, microwave, oven, stovetop

Charming Chicopee Getaway

The price is AED 533
AED 1,208 total
includes taxes & fees
10 Jun - 11 Jun
Charming Chicopee Getaway
Charming Apartment In Berkshire Victorian Home
Interior

Charming Apartment In Berkshire Victorian Home

7.8 out of 10, Good, (7)
"This adorable place is central to Pittsfield and made it really easy for my daughter and I go get where we needed to be. It’s a clean, great space. We’ll definitely be back!"
Charming Apartment In Berkshire Victorian Home
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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Other property types in Chester

The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The Ponds at Foxhollow
Deluxe Queen Room with 2 Queen Beds
1 bedroom, WiFi, bed sheets

Deluxe Queen Room with 2 Queen Beds

2.0 star property
The price is AED 437
AED 570 total
includes taxes & fees
11 May - 12 May
Deluxe Queen Room with 2 Queen Beds
Cozy Home in Holyoke with 2 bedrooms
Fridge, microwave, oven, stovetop

Cozy Home in Holyoke with 2 bedrooms

10.0 out of 10, Exceptional, (4)
"We stayed in Holyoke as my daughter was performing at UMASS Amherst and this was a great location only 25 minutes of so away from campus. The home is spacious with two bedrooms and bathrooms. A very clean and well maintained the home. Would definitely recommend and will visit again!! "
The price is AED 477
AED 1,063 total
includes taxes & fees
12 May - 13 May
Cozy Home in Holyoke with 2 bedrooms
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.

Frequently asked questions

What's it like to stay at an apartment in Chester?
You might have as many choices centrally in Chester, but Expedia can help you search for lodging options in the area with similar amenities to an apartment. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment like a kitchen. Even filter by similar properties such as vacation homes, condos, or cabins.
How do you know if an apartment is the right choice for you?
Offering a kitchen for convenient meals, an apartment often has more space than a traditional hotel room. Apartments are a good option for couples who want to live like locals, and also for families who want the conveniences of home.
What's the best apartment for a stay in Chester?
Listed below are some of the top apartments in the area to choose from: Charming Apt in 18th c Berkshire Farmhouse: Located in Lanesborough, 22 mi/35.3 km from the heart of Chester. Includes fireplaces. Access to onsite laundry facilities is available on site. Chic Downtown Retreat Furnished 2-Bedroom with Trail Access & Outdoor Oasis: Located 15.8 mi/25.5 km away in Easthampton. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located in Lee, 14 mi/22.6 km away. Includes private patios and fireplaces. Access to onsite laundry facilities is available on site. Easthampton Apartment Near Breweries & Rail Trail!: It’s situated in Easthampton, 16.2 mi/26.1 km from Chester.
What can I expect from the weather during my trip to Chester?
Weather is only one factor, but it can really affect your travel plans, especially when you are planning a longer stay in Chester. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.
What should I see in Chester?
Explore the area and cultural attractions such as Chester Town Hall, or visit a family-friendly sight such as Congregation Beth Israel. In the larger area, you’ll find Glendale Falls and Iroquis Waterfront.
What's the best way to get to and around Chester?
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 15.4 mi (24.7 km) away from the heart of the city. You can also search for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 18.9 mi (30.4 km) away. If you’d like to venture out around the area, consider renting a car to take in more sights.