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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sep - 14 Sep
In two months
10 Oct - 12 Oct

Apartments in Chester

Easthampton Vacation Rental - Walk to Breweries!
Interior

Easthampton Vacation Rental - Walk to Breweries!

9.6 out of 10, Exceptional, (21)
"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
1 bedroom, WiFi, bed sheets

Charming Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (34)
"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
13 Aug - 14 Aug
Charming Apt in 18th c Berkshire Farmhouse
Charming Chicopee Getaway
Fridge, microwave, oven, stovetop

Charming Chicopee Getaway

The price is AED 426
AED 1,071 total
includes taxes & fees
9 Sep - 10 Sep
Charming Chicopee Getaway
Button's Modern Luxury Walkup Downtown Northampton
Oven, stovetop, dishwasher

Button's Modern Luxury Walkup Downtown Northampton

The price is AED 918
AED 1,850 total
includes taxes & fees
13 Aug - 14 Aug
Button's Modern Luxury Walkup Downtown Northampton
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, (63)
"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
Spacious apartment near Holyoke Medical Center + dedicated office area
Fridge, microwave, oven, stovetop

Spacious apartment near Holyoke Medical Center + dedicated office area

10.0 out of 10, Exceptional, (1)
"This newly remodeled apartment was clean and spacious with quality furniture, bedding and linens. It is in a residential area with easy access to highway and great area local restaurants. "
Spacious apartment near Holyoke Medical Center + dedicated office area
Peaceful Meadow Retreat
Terrace/patio

Peaceful Meadow Retreat

2.0 star property
10.0 out of 10, Exceptional, (9)
"Quite and very clean"
The price is AED 443
AED 794 total
includes taxes & fees
24 Aug - 25 Aug
Peaceful Meadow Retreat
Downtown Gateway to the Berkshires. Walk to Everything.
Exterior detail

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.
Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge
Living area

Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge

9.0 out of 10, Wonderful, (2)
"The apartment is in downtown Stockbridge. We were there to aid our son and his fiancee who are traversing the Appalachia Trail. The location was perfect for us. The apartment is complete new and immaculate. It was very comfortable for the four of us. The only reason that the overall review is four not five stars is that the dryer wasn't working and the kitchen had absolutely now supplies or an ice tray. The dryer not working could have been a disaster for us as we needed to clean our son's...
Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Fridge, microwave, oven, stovetop

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

2.0 star property
9.8 out of 10, Exceptional, (8)
"Clean and well stock"
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Gateway to the Berkshires - Renovated downtown apartment
Exterior

Gateway to the Berkshires - Renovated downtown apartment

10.0 out of 10, Exceptional, (8)
"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
Elm Suite with a Private Bathroom in front of Smith College Quadrangle
Exterior detail

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

9.6 out of 10, Exceptional, (19)
"Great resonably priced place to stay in Northampton. Very walkable to shops and restaurants. "
Elm Suite with a Private Bathroom in front of Smith College Quadrangle
Easthampton Apartment Near Breweries & Rail Trail!
Interior

Easthampton Apartment Near Breweries & Rail Trail!

9.6 out of 10, Exceptional, (17)
"The apartment was great, and the location to restaurants and breweries was awesome. "
Easthampton Apartment Near Breweries & Rail Trail!
Bright Boho Apt in 18th c Berkshire Farmhouse
Property grounds

Bright Boho Apt in 18th c Berkshire Farmhouse

9.0 out of 10, Wonderful, (22)
"Really enjoyed our stay"
The price is AED 533
AED 808 total
includes taxes & fees
13 Aug - 14 Aug
Bright Boho Apt in 18th c Berkshire Farmhouse
Birch Suite- 2nd Floor Apartment with Kitchenette in front of Smith College
Exterior

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

10.0 out of 10, Exceptional, (15)
"A warm reception and great accommodations. Location is ideal for Smith and Mount Holyoke."
Birch Suite- 2nd Floor Apartment with Kitchenette in front of Smith College
Heart of Lenox!! - renovated downtown apartment
Exterior

Heart of Lenox!! - renovated downtown apartment

10.0 out of 10, Exceptional, (70)
"Beautiful property in a perfect location for a girls ski weekend getaway! "
Heart of Lenox!! - renovated downtown apartment
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Fridge, microwave, oven, stovetop

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (62)
"Great value, so much better than all the touristy motels in the area!"
The price is AED 496
AED 763 total
includes taxes & fees
17 Aug - 18 Aug
Cozy Rustic Apt in 18th c Berkshire Farmhouse
The Penthouse, Downtown Lenox by Evergreen Home
Fridge, microwave, oven, stovetop

The Penthouse, Downtown Lenox by Evergreen Home

10.0 out of 10, Exceptional, (8)
"Amazing space and location!"
The Penthouse, Downtown Lenox by Evergreen Home
Bright Springfield Apartment w/ 2 Balconies!
Apartment (3 Bedrooms) | Interior

Bright Springfield Apartment w/ 2 Balconies!

3.0 star property
Bright Springfield Apartment w/ 2 Balconies!
Charming Apartment In Berkshire Victorian Home
Interior

Charming Apartment In Berkshire Victorian Home

8.2 out of 10, Very Good, (12)
"We enjoyed our stay! It’s a beautiful big old house in a lovely neighborhood. We were a large group and it was comfortable and roomy for all of us. "
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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Top Chester Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Nice pool"
Carol 1-night trip
Posted 11 hours ago
The Yankee, Trademark Collection by Wyndham

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: Easthampton Vacation Rental - Walk to Breweries!: Situated in Easthampton, 16.2 mi/26.1 km from the heart of Chester. Includes sofa beds. Charming Chicopee Getaway: Located 22.2 mi/35.8 km away in Chicopee. Charming Apt in 18th c Berkshire Farmhouse: Located in Lanesborough, 22 mi/35.3 km away. Includes fireplaces. Access to onsite laundry facilities is available on site. Button's Modern Luxury Walkup Downtown Northampton: Located 17.9 mi/28.7 km away in Northampton. Amenities include Smart TVs. Access to onsite laundry facilities 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 Pyramid Lake.
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.