Photo by Elizabeth Massa Peroulakis

Apartments in Chester for Rent

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Apartments in Chester

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (65)
"Great value, so much better than all the touristy motels in the area!"
$189 nightly
The price is $208
Oct 2 - Oct 3
Total with taxes and fees
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse

9.4 out of 10, Exceptional, (38)
"It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host."
$189 nightly
The price is $208
Oct 2 - Oct 3
Total with taxes and fees
Charming Apt in 18th c Berkshire Farmhouse

Charming Chicopee Getaway

10.0 out of 10, Exceptional, (1)
"We really appreciated the stay to get together with family. There was plenty of space to play with the toddler and set up the pack-n-play for the infant. And then plenty of room to play board games after the babies were put to bed. "
$231 nightly
The price is $269
Oct 7 - Oct 8
Total with taxes and fees
Charming Chicopee Getaway

51 Church Street, Lenox MA - One Bedroom Unit

10.0 out of 10, Exceptional, (33)
"Clean, comfortable and great location."
51 Church Street, Lenox MA - One Bedroom Unit

Charming 1-BR Apartment in Conway, WiFi/AC

10.0 out of 10, Exceptional, (1)
"I rented this property for a ski week end. The place is beautifully decorated, very spacious and fully equipped. Located 30min from berkshire east mountain, it was a perfect choice."
Charming 1-BR Apartment in Conway, WiFi/AC

Downtown Gateway to the Berkshires. Walk to Everything.

2.0 star property
8.0 out of 10, Very Good, (1)
"This cute and cozy apartment was in an excellent location. We were the first guest to stay here and we had a few concerns: the chairs in the kitchen were broken as was a door frame. The command hooks fell off the several times. There was no place to hang clothes and shelves which held the dishes were dirty and dusty as well as appliances. Some coffee and Kleenex would have a nice. The place has the potential to be amazing with a little more attention to details. We have stayed in many, many...
Downtown Gateway to the Berkshires. Walk to Everything.

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

9.4 out of 10, Exceptional, (68)
"Location cannot be outdone. This rental was spacious, well stocked, extremely clean, and a very responsive kind owner. Highly recommended:)"
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Welcoming studio near Holyoke Medical Center + free wifi

10.0 out of 10, Exceptional, (1)
Welcoming studio near Holyoke Medical Center + free wifi

The Studio mini home away from home in the Berkshires

9.6 out of 10, Exceptional, (29)
"Great place to stay in Berkshires."
The Studio mini home away from home in the Berkshires

Spacious apartment near Holyoke Medical Center + dedicated office area

10.0 out of 10, Exceptional, (2)
"Perfect property and location for visiting the several surrounding communities."
Spacious apartment near Holyoke Medical Center + dedicated office area

Button's Modern Luxury Walkup Downtown Northampton

10.0 out of 10, Exceptional, (1)
"This was the best rental apartment I've stayed at and definitely the cleanest. Check-in is easy, the pictures are accurate, the kitchen and bathroom are great, and the location in downtown Northampton is super walkable to cafes, shops, Smith, etc. If I'm ever back anywhere near the area, I will definitely try to stay there again. 10/10"
Button's Modern Luxury Walkup Downtown Northampton

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

9.8 out of 10, Exceptional, (21)
"Lovely space and lovely host, great value!"
Elm Suite with a Private Bathroom in front of Smith College Quadrangle

The Serendipity Spot

10.0 out of 10, Exceptional, (1)
"Very comfortable, soft bed, cute decor and very convenient location for Great Barrington and surrounding area. Owners are kind, ready to help whenever you need something. Overall this is a great place to stay and we highly recommend it to anyone spending some time in the area. "
The Serendipity Spot

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

10.0 out of 10, Exceptional, (17)
"4 days in town, loved the quiet retreat. Had everything i needed. Slept well all 4 nights. "
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, (18)
"Loved staying here! Communication and access were so easy, as was getting around town from this location. Will stay again!"
Maple Suite- Private Ground Floor Apartment in front of Smith College

Heart of Lenox!! - renovated downtown apartment

10.0 out of 10, Exceptional, (71)
"Beautiful property in a perfect location for a girls ski weekend getaway! "
Heart of Lenox!! - renovated downtown apartment

Easthampton Apartment Near Breweries & Rail Trail!

3.0 star property
Easthampton Apartment Near Breweries & Rail Trail!

Humble home with free breakfast

7.0 out of 10, Good, (2)
$277 nightly
The price is $323
Oct 27 - Oct 28
Total with taxes and fees
Humble home with free breakfast

Gateway to the Berkshires - Renovated downtown apartment

10.0 out of 10, Exceptional, (9)
"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

1500 sqft private entrance with beautiful views of the Berkshire Mountains

10.0 out of 10, Exceptional, (46)
"Perfect get away, convenient to everything."
1500 sqft private entrance with beautiful views of the Berkshire Mountains
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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Top Chester Hotel Reviews

Find out more about Chester

Find out more about Chester

Chester Apartments information

Number of reviews
401
Accommodation
78 Apartments
Lowest Price
$208
Highest Price
$323

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