Photo by Elizabeth Massa Peroulakis

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Check prices for these dates

Next weekend
14 Rab. I - 16 Rab. I
In two weeks
21 Rab. I - 23 Rab. I
In one month
4 Rab. II - 6 Rab. II
In two months
2 Jum. I - 4 Jum. I

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

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, (10)
"Our group had a wonderful time and we will not hesitate to book again in the future. The place was exceptionally clean, well appointed, and very comfortable. Overall it was a great experience! "
Easthampton Vacation Rental - Walk to Breweries!
Charming Apt in 18th c Berkshire Farmhouse
Miscellaneous

Charming Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (31)
"The space was cozy and clean and the owners were very easy to communicate with and knowledgeable about the area. The bathroom has very fun lights. "
The price is SAR 506
SAR 779 total
includes taxes & fees
7 Mar - 8 Mar
Charming Apt in 18th c Berkshire Farmhouse
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
Smart TV, offices

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!
Interior

Easthampton Apartment Near Breweries & Rail Trail!

9.6 out of 10, Exceptional, (8)
"Wonderful place. Communication was lovely for early entry. Needs more direction on where to put trash. "
Easthampton Apartment Near Breweries & Rail Trail!
Chic Downtown Retreat Furnished 2-Bedroom with Trail Access & Outdoor Oasis
Private kitchen

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

Chic Downtown Retreat Furnished 2-Bedroom with Trail Access & Outdoor Oasis
Renovated Downtown 1bedroom
Stovetop, dishwasher

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
Terrace/patio

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

9.4 out of 10, Exceptional, (61)
"3 day holiday getaway, my husband and our 2 pups. A hike in nearby trails in the woods, enjoyed Lee downtown eateries and shops. Beautiful winter wonderland in the Berkshires. The guest rental was perfect!!! Warm, spacious, comfortable, perfect location. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Miscellaneous

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (61)
"The owner was very responsive. It is a very unique and cozy place, and we had a nice time. Thank you!"
The price is SAR 506
SAR 779 total
includes taxes & fees
8 Mar - 9 Mar
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Bright Boho Apt in 18th c Berkshire Farmhouse
Miscellaneous

Bright Boho Apt in 18th c Berkshire Farmhouse

8.8 out of 10, Excellent, (20)
"This location was great for our event at Tanglewood. Perfect little apartment for my husband and i to spend the night. Walked to get coffee in the morning. Would have loved to shop at the farm store, but we weren't there when it was open. Would absolutley stay here again of we're ever in the Berkshires again!"
The price is SAR 544
SAR 825 total
includes taxes & fees
7 Mar - 8 Mar
Bright Boho Apt in 18th c Berkshire Farmhouse
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, (25)
"This property hit the 5 star marks all over. Access was amazing to our weekend. Host was so precise with check in instruction and overall information. This property was very very clean, comfortable and the light that entered all of the rooms made the stay warm and inviting. 5 Star for us. "
51 Church Street, Lenox MA - One Bedroom Unit
Gateway to the Berkshires - Renovated downtown apartment
Exterior

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
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
Peaceful Meadow Retreat
Terrace/patio

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!
Property grounds

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
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
Cozy First Floor Apartment. Located in a quiet neighborhood.
Outdoor dining

Cozy First Floor Apartment. Located in a quiet neighborhood.

8.8 out of 10, Excellent, (3)
"Loved our stay here!"
Cozy First Floor Apartment. Located in a quiet neighborhood.
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Living area

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

2.0 star property
The price is SAR 563
SAR 830 total
includes taxes & fees
7 Mar - 8 Mar
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
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, (5)
"Great property and communication!"
The price is SAR 863
SAR 1,483 total
includes taxes & fees
21 Mar - 22 Mar
Low-scent, historic downtown gem with sustainability practices throughout.
Apartment in Gorgeous Stonybrook Farm
1 bedroom, in-room safe, iron/ironing board, free WiFi

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
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
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

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 SAR 563
SAR 855 total
includes taxes & fees
7 Mar - 8 Mar
Berkshire Village Carriage House - Super Private!!
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace, DVD player

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: Chic Downtown Retreat Furnished 2-Bedroom with Trail Access & Outdoor Oasis: Situated in Easthampton, 15.8 mi/25.5 km from the heart of Chester. 1500 sqft private entrance with beautiful views of the Berkshire Mountains: Located 13.8 mi/22.1 km away in Lee. Free WiFi, private patios, and Smart TVs are included. Charming Chicopee Getaway: It’s located in Chicopee, 22.2 mi/35.8 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 Bousquet Ski Area. 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.