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

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!

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!

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

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.

10.0 out of 10, Exceptional, (6)
"Great property and communication!"
The price is AED 676
AED 1,243 total
includes taxes & fees
19 May - 20 May
Low-scent, historic downtown gem with sustainability practices throughout.

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

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

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!

9.6 out of 10, Exceptional, (14)
"Very clean, straightforward instructions, and great area"
Easthampton Vacation Rental - Walk to Breweries!

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

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 763 total
includes taxes & fees
19 May - 20 May
Charming Apt in 18th c Berkshire Farmhouse

Upstairs on Main with private bathroom

9.2 out of 10, Wonderful, (32)
"We enjoyed our stay in this great place! cute little upstairs apartment with a great use of space and perfect for getting around the area. We got the benefit of a beautiful snow storm too (and the walk and parking area were shoveled when we woke up which was nice!) thanks again."
Upstairs on Main with private bathroom

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

2.0 star property
The price is AED 551
AED 804 total
includes taxes & fees
31 May - 1 Jun
Chic corporate apartment in wonderful Pittsfield with AC, WiFi

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

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

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

9.6 out of 10, Exceptional, (62)
"The owner was very responsive. It is a very unique and cozy place, and we had a nice time. Thank you!"
The price is AED 496
AED 763 total
includes taxes & fees
19 May - 20 May
Cozy Rustic Apt in 18th c Berkshire Farmhouse

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

The price is AED 419
AED 1,079 total
includes taxes & fees
26 May - 27 May
Charming Chicopee Getaway

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

3.0 star property
8.6 out of 10, Excellent, (121)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow

Deluxe Queen Room with 2 Queen Beds

2.0 star property
The price is AED 437
AED 570 total
includes taxes & fees
25 May - 26 May
Deluxe Queen Room with 2 Queen Beds

Cozy Home in Holyoke with 2 bedrooms

9.6 out of 10, Exceptional, (5)
"Wonderful stay. Veronica was so kind and super responsive. The house was a great size and have everything we needed. We stayed there with 2 adults and 2 toddlers under 3. It was plenty of space. And a great location to all the area had to offer, museums, fun restaurants in North Hampton, etc. Would definitely stay again. "
The price is AED 569
AED 1,178 total
includes taxes & fees
19 May - 20 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. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located 14 mi/22.6 km away in Lee. Private patios and fireplaces are included. Access to onsite laundry facilities is available on site. Easthampton Apartment Near Breweries & Rail Trail!: It’s located in Easthampton, 16.2 mi/26.1 km away. Elm Suite with a Private Bathroom in front of Smith College Quadrangle: Located in Northampton, 17.5 mi/28.1 km from Chester. Includes jetted bathtubs. Access to a hot tub is available on site.
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.