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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 62 Apartments in Chester with updated reviews, rates, and availability.

Easthampton Vacation Rental - Walk to Breweries!
Easthampton Vacation Rental | 2BR | 1BA | 900 Sq Ft | Access Only By Stairs

Easthampton Vacation Rental - Walk to Breweries!

9.6 out of 10, Exceptional, (9)
"Very clean, straightforward instructions, and great area"
Easthampton Vacation Rental - Walk to Breweries!
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)
"Perfect location. Walking distance. Brand new apartment. "
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
The Penthouse, Downtown Lenox by Evergreen Home
Gorgeous open concept living room

The Penthouse, Downtown Lenox by Evergreen Home

10.0 out of 10, Exceptional, (7)
"This is the second year we had our girls weekend at the Penthouse and it did not disappoint. The place is updated, very clean, and in a great location! Only suggestion would to get a nice big sectional couch! We had 8 people and not enough comfy seating. But beautiful apartment!! "
The Penthouse, Downtown Lenox by Evergreen Home
Easthampton Apartment Near Breweries & Rail Trail!
Easthampton Vacation Rental | 2BR | 1BA | 900 Sq Ft | Access Only By Stairs

Easthampton Apartment Near Breweries & Rail Trail!

9.4 out of 10, Exceptional, (6)
"The space was just what we needed for a reading retreat weekend. The house was clean and the beds were comfortable. Walking distance to main strip and a few local shops. Recommendations for the owner: add a few wine glasses & a drying mat/rack. Everything was in great working order. "
Easthampton Apartment Near Breweries & Rail Trail!
Chic Downtown Retreat Furnished 2-Bedroom with Trail Access & Outdoor Oasis
Living area

Chic Downtown Retreat Furnished 2-Bedroom with Trail Access & Outdoor Oasis

Chic Downtown Retreat Furnished 2-Bedroom with Trail Access & Outdoor Oasis
Elm Suite with a Private Bathroom in front of Smith College Quadrangle
Exterior

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

9.6 out of 10, Exceptional, (13)
"The weather was beautiful, so the main room was full of bright sunlight during the days. I enjoyed soaking in the large tub a couple of evenings and spent some time in town enjoying music and a show. This was just what I needed to decompress for a few days as I prepared to start a new job. "
Elm Suite with a Private Bathroom in front of Smith College Quadrangle
Renovated Downtown 1bedroom
Living area

Renovated Downtown 1bedroom

10.0 out of 10, Exceptional, (22)
"We’ve always had a great experience with Downtown Upstairs in Lenox and this was no exception. Easy access to the downtown stores and restaurants with the comfort of a nice, clean, well furnished apartment. "
Renovated Downtown 1bedroom
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Exterior

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

9.4 out of 10, Exceptional, (60)
"The property was fine for our purposes of visiting family. If we needed to cook, it would have been quite difficult, though not totally impossible. The furniture was comfortable and the rooms, except the kitchen, had plenty of space. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
51 Church Street, Lenox MA - One Bedroom Unit
Living area

51 Church Street, Lenox MA - One Bedroom Unit

10.0 out of 10, Exceptional, (24)
"Lovely apartment in a great location "
51 Church Street, Lenox MA - One Bedroom Unit
Gateway to the Berkshires - Renovated downtown apartment
Room

Gateway to the Berkshires - Renovated downtown apartment

10.0 out of 10, Exceptional, (7)
"Thanks, Emmy, for a great visit. The apartment was exactly what we hoped for, clean and convenient to downtown and to all things in the Berkshires. We explored and relaxed and thoroughly enjoyed our getaway over a beautiful October weekend. I'd recommend the apartment to anyone who wants that in-town setting and wishes to explore all that the area has to offer. Great host, thank you!"
Gateway to the Berkshires - Renovated downtown apartment
The Studio mini home away from home in the Berkshires
Exterior

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
Peaceful Meadow Retreat
Property grounds

Peaceful Meadow Retreat

2.0 star property
10.0 out of 10, Exceptional, (8)
"As usual very nice stay on property! Would recommend to everyone. Spacious, clean and quiet location!"
Peaceful Meadow Retreat
Bright Springfield Apartment w/ 2 Balconies!
Springfield Vacation Rental | 3BR | 1BA | Stairs Required | 1,500 Sq Ft

Bright Springfield Apartment w/ 2 Balconies!

9.6 out of 10, Exceptional, (8)
"The apartment was very nice and roomy. Perfect size for our needs. Although the listing did show/state stair access required, I thought it was a two story with bedrooms upstairs. My elderly father whom we came out to visit had a very difficult time climbing stairs. Had some trouble with the code upon arrival but contacted host and she responded immediately and solved the issue. Overall house was clean with minimum issues. I would recommend this house to friends and family and would rent again....
Bright Springfield Apartment w/ 2 Balconies!
Charming Apartment In Berkshire Victorian Home
Exterior

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
Cozy First Floor Apartment. Located in a quiet neighborhood.
Private kitchen

Cozy First Floor Apartment. Located in a quiet neighborhood.

10.0 out of 10, Exceptional, (2)
"Loved our stay here!"
Cozy First Floor Apartment. Located in a quiet neighborhood.
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Room

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

2.0 star property
The price is AED 551
AED 812 total
includes taxes & fees
28 Feb - 1 Mar
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Low-scent, historic downtown gem with sustainability practices throughout.
Locally made furniture and Karastan rug.

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

10.0 out of 10, Exceptional, (5)
"Great property and communication!"
Low-scent, historic downtown gem with sustainability practices throughout.
Apartment in Gorgeous Stonybrook Farm

Apartment in Gorgeous Stonybrook Farm

9.4 out of 10, Exceptional, (44)
"This was a beautifully appointed property on an estate overlooking a pond. The apartment was spotless and the caretaker was most helpful when we needed anything. The rooms were well supplied and perfect for us. Thank you for letting us experience the quintessence of the Berkshires."
Apartment in Gorgeous Stonybrook Farm
Birch Suite- 2nd Floor Apartment with Kitchenette
Exterior

Birch Suite- 2nd Floor Apartment with Kitchenette

10.0 out of 10, Exceptional, (12)
"I was visiting my granddaughter at Smith during family weekend and the location was perfect, right across the street from Paradise Road, a few minutes walk from her apartment. It’s within easy walking distance of everything on campus and a fairly short walk to town. I didn’t rent a car for this trip and walked from the Northampton Amtrak station with no problem. This is the upstairs apartment and the stairs are steep but there’s a sturdy handrail. The apartment is very comfortable, light and...
Birch Suite- 2nd Floor Apartment with Kitchenette
Upstairs on Main with private bathroom
Exterior

Upstairs on Main with private bathroom

9.2 out of 10, Wonderful, (31)
"Check in was easy, beds are comfortable. I’m a big and tall guy, so only qualm I had was the small toilet, and low shower head. Aside from those, great stay!"
Upstairs on Main with private bathroom
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 price is AED 438
AED 489 total
includes taxes & fees
23 Feb - 24 Feb
The Ponds at Foxhollow
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is AED 551
AED 841 total
includes taxes & fees
23 Feb - 24 Feb
Berkshire Village Carriage House - Super Private!!
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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: 1500 sqft private entrance with beautiful views of the Berkshire Mountains: Situated in Lee, 13.8 mi/22.1 km from the heart of Chester. Includes free WiFi, private patios, and Smart TVs. Charming Chicopee Getaway: Located 22.2 mi/35.8 km away in Chicopee. Chic Downtown Retreat Furnished 2-Bedroom with Trail Access & Outdoor Oasis: It’s located in Easthampton, 15.8 mi/25.5 km away. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: 14 mi/22.6 km away in Lee. Private patios and fireplaces are included. 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 The Bookstore. 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.