Photo by Elizabeth Massa Peroulakis

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Compare 59 Apartments in Chester with updated reviews, rates, and availability.

Easthampton Apartment Near Breweries & Rail Trail!
Easthampton Vacation Rental | 2BR | 1BA | 900 Sq Ft | Access Only By Stairs
Easthampton Apartment Near Breweries & Rail Trail!
10.0 out of 10, Exceptional, (1)
"nice place. not sure where the garbage cans are . used the one at 27"
Easthampton Apartment Near Breweries & Rail Trail!
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
9.4 out of 10, Exceptional, (10)
"Great location and value. Furnishings are basic but the bed is comfortable and the location is great. Communication is excellent and host fixed an internet issue immediately. I will definitely look forward to returning. Could have a better more accessible coffee maker would be my only suggestion :)"
Elm Suite with a Private Bathroom in front of Smith College Quadrangle
Peaceful Meadow Retreat
Property grounds
Peaceful Meadow Retreat
2.0 star property
10.0 out of 10, Exceptional, (5)
"Excellent Host, exceptional property!"
The price is AED 382
AED 724 total
includes taxes & fees
17 Oct - 18 Oct
Peaceful Meadow Retreat
Gateway to the Berkshires - Renovated downtown apartment
Room
Gateway to the Berkshires - Renovated downtown apartment
10.0 out of 10, Exceptional, (6)
"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
Garfield House Studio at 208
Exterior
Garfield House Studio at 208
9.8 out of 10, Exceptional, (24)
"A great location for a number of cultural experiences in the Berkshires, and walking distance to the shops and restaurants of the town of Lee. The studio is small, but the murphy bed is incredibly comfortable so it has all the benefits of a hotel room, with the addition of a kitchen and a porch from which to watch the world of Lee go by."
Garfield House Studio at 208
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Cozy Rustic Apt in 18th c Berkshire Farmhouse
9.6 out of 10, Exceptional, (59)
"Beautiful property with flower farm, pick your own berries and vegetable farm stand. Rustic log cabin feel with all amenities needed with kitchen."
The price is AED 533
AED 793 total
includes taxes & fees
22 Sep - 23 Sep
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Charming Apt in 18th c Berkshire Farmhouse
Charming Apt in 18th c Berkshire Farmhouse
9.8 out of 10, Exceptional, (27)
"I was just there for one night but the place was comfortable, clean, and equipped for everything I might possibly need. The hosts were lovely and proactive in their communication. Would stay again!"
The price is AED 533
AED 793 total
includes taxes & fees
22 Sep - 23 Sep
Charming Apt in 18th c Berkshire Farmhouse
Cozy First Floor Apartment. Located in a quiet neighborhood.
Private kitchen
Cozy First Floor Apartment. Located in a quiet neighborhood.
Cozy First Floor Apartment. Located in a quiet neighborhood.
51 Church Street, Lenox MA - One Bedroom Unit
Living area
51 Church Street, Lenox MA - One Bedroom Unit
10.0 out of 10, Exceptional, (19)
"Fine"
51 Church Street, Lenox MA - One Bedroom Unit
Farmhouse-Loft -48 Main Street, Lenox, MA
Dining
Farmhouse-Loft -48 Main Street, Lenox, MA
10.0 out of 10, Exceptional, (6)
"Absolutely wonderful location, the loft itself was amazing i think the online pictures did not do it justice, beautifully decorated, spacious, clean, close to main attractions , very comfortable setting, communication with owners was kind, thoughtful and helpful, would absolutely recomend."
Farmhouse-Loft -48 Main Street, Lenox, MA
Convenient Springfield Apartment 3 Mi to Downtown!
Private kitchen
Convenient Springfield Apartment 3 Mi to Downtown!
3.0 star property
Convenient Springfield Apartment 3 Mi to Downtown!
Great First Floor Apartment close to many local attractions!
Exterior
Great First Floor Apartment close to many local attractions!
10.0 out of 10, Exceptional, (1)
"The apartment is clearly updated and kept up well. It was clean and smelled so good upon our arrival. Our family of 5 fit great and were very comfortable! The owner was extremely communicative and had all the basics ready for us. We look forward to staying again next time we’re in town to see family! Thank you!!"
Great First Floor Apartment close to many local attractions!
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, (8)
"We liked this property a lot! PROS: Great location, very clean, and clear communication with hosts. We will plan to stay again and have my in laws rent out the duplex unit next door. Be sure to check out the co-op grocery store 5 min away - so good. CONS The bathroom is VERY small and the door doesn’t close all the way. Be advised that plugging in the hair dryer with the AC unit running will short out the upstairs power. Glad it was easy to reset. Also, having more TP and paper towels...
Easthampton Vacation Rental - Walk to Breweries!
Cozy Berkshires Vacation Rental Near Hiking!
Chester Vacation Rental | 2BR | 1BA | 2,000 Sq Ft | Stairs Required
Cozy Berkshires Vacation Rental Near Hiking!
10.0 out of 10, Exceptional, (1)
"The stay at the property was enjoyable. The space was large, spacious and very clean. Two people were able to stay quite comfortably."
Cozy Berkshires Vacation Rental Near Hiking!
Humble home with free breakfast
Humble home with free breakfast
4.0 out of 10, (1)
"The place was not very clean, furniture was awful, and we were also given the wrong door code to get it. "
The price is AED 474
AED 992 total
includes taxes & fees
22 Oct - 23 Oct
Humble home with free breakfast
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
Charming Apartment In Berkshire Victorian Home
Exterior
Charming Apartment In Berkshire Victorian Home
6.0 out of 10, (3)
"We came for a weekend stay to attend a concert at Tanglewood. Upon arrival, we saw a lot of construction materials in the yard including a saw and piles of materials. The grounds were not well maintained. Check-in was easy enough but when we got into the apartment, we noted that it had not been cleaned. Food crumbs on the floors, unclean bathroom, particularly the shower (which was so dirty we had to bleach it ourselves. We also noted that one of the exit ways was cluttered which could have been...
The price is AED 731
AED 1,280 total
includes taxes & fees
3 Oct - 4 Oct
Charming Apartment In Berkshire Victorian Home
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!
Cozy Springfield Apartment, Close to Parks!
Springfield Vacation Rental | 3BR | 1BA | Stairs Required | 1,500 Sq Ft
Cozy Springfield Apartment, Close to Parks!
10.0 out of 10, Exceptional, (6)
"The house was clean and very comfortable. We would rent this house again."
Cozy Springfield Apartment, Close to Parks!
Free coffee a comfortable bed food and drinks
Free coffee a comfortable bed food and drinks
4.0 out of 10, (2)
"My room es cancelled by owner"
Free coffee a comfortable bed food and drinks
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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

Cozy Berkshires Vacation Rental Near Hiking!
Chester Vacation Rental | 2BR | 1BA | 2,000 Sq Ft | Stairs Required
Cozy Berkshires Vacation Rental Near Hiking!
10.0 out of 10, Exceptional, (1)
"The stay at the property was enjoyable. The space was large, spacious and very clean. Two people were able to stay quite comfortably."
Cozy Berkshires Vacation Rental Near Hiking!
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
The Lake-we provide kayaks and a canoe!
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (205)
"My stay was shorter than I had planned but the few days I was here was so relaxing. First of all, the bed is so comfortable, I slept like a baby. Very quiet area. Nice to walk around with my dogs and explore. The cottage was nicely outfitted with any needs you might have. Beautiful time of year to stay here! I cannot wait to go back. I also want to say I appreciate that they allowed my two dogs. My dogs are very well behaved, and I travel with them quite often. Not all places allow this, so I...
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Cozy apartment located in quiet Williamsburg
Exterior
Cozy apartment located in quiet Williamsburg
9.6 out of 10, Exceptional, (41)
"Property was as advertised. Easy to get in and was exactly what we were looking for. "
The price is AED 551
AED 951 total
includes taxes & fees
22 Sep - 23 Sep
Cozy apartment located in quiet Williamsburg
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 more popular apartments in the area to choose from: Cozy Berkshires Vacation Rental Near Hiking!: Includes sofa beds. Access to a game room is available on site. Garfield House Studio at 208: It’s located in Lee, 14.1 mi/22.6 km away. Elm Suite with a Private Bathroom in front of Smith College Quadrangle: 17.5 mi/28.1 km away in Northampton. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: It’s located in Lee, 14 mi/22.6 km from Chester. Includes private patios and fireplaces.
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. Average annual precipitation for Chester is 62 inches.
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 Jacob’s Pillow and Otis Reservoir.
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.