Photo by Elizabeth Massa Peroulakis

Search Apartments in Chester

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Compare 61 Apartments in Chester with updated reviews, rates, and availability.

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

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

The price is AED 724
AED 1,161 total
includes taxes & fees
30 Nov - 1 Dec
Chic Downtown Retreat Furnished 2-Bedroom with Trail Access & Outdoor Oasis
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, (59)
"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
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, (12)
"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
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, (6)
"Amazing space and location!"
The Penthouse, Downtown Lenox by Evergreen Home
Charming 2-bedroom apartment in downtown Stockbridge with AC, WiFi
Living area

Charming 2-bedroom apartment in downtown Stockbridge with AC, WiFi

Charming 2-bedroom apartment in downtown Stockbridge with AC, WiFi
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (60)
"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 797 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Main Street Delight 1bedroom
Living area

Main Street Delight 1bedroom

10.0 out of 10, Exceptional, (18)
"The location was fantastic for our stay in the Berkshires. Walkable to many restaurants & shops. It was very well decorated & cozy. Very convenient being above a coffee shop, however not ideal if you enjoy sleeping in. We could hear the consistent squeaking of the coffee shop door as soon as it opened in the morning (~7:00 am) from the bedroom. However, good motivation to get up and enjoy the beautiful Berkshires!"
Main Street Delight 1bedroom
Maple Suite- Private Ground Floor Apartment
Bathroom

Maple Suite- Private Ground Floor Apartment

9.6 out of 10, Exceptional, (10)
"I loved everything about it. My granddaughters came over to help bake cookies and make charm bracelets. Then showered and got bedtime stories from Nana before heading back to their home. Great location."
Maple Suite- Private Ground Floor Apartment
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!
Renovated Downtown 1bedroom
Living area

Renovated Downtown 1bedroom

10.0 out of 10, Exceptional, (21)
"Location, location, location. Great use of space in this nicely decorated, conveniently located apt. Steps away from restaurants and shopping. 7 minutes from Kripalu. Great communication from owner. Looking forward to next stay."
Renovated Downtown 1bedroom
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, (2)
"Very clean and nicely decorated apartment in center of town. Great location. Really enjoyed our vacation."
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Property grounds

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

2.0 star property
9.4 out of 10, Exceptional, (3)
"Clean and well stock"
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
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!
Garfield House Studio at 208
Exterior

Garfield House Studio at 208

9.6 out of 10, Exceptional, (28)
"Zero complaints. Perfect location"
Garfield House Studio at 208
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 378
AED 893 total
includes taxes & fees
2 Dec - 3 Dec
Humble home with free breakfast
Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (30)
"Some friends and I were in town for a wedding and were just staying the night and the property was perfect for what we needed! It was very clean and well-maintained. The only minor thing was the building is close to the road and we could hear some traffic at night, but it wasn’t too disruptive. We really enjoyed our stay, thank you!"
The price is AED 533
AED 797 total
includes taxes & fees
28 Nov - 29 Nov
Charming Apt in 18th c Berkshire Farmhouse
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

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, (1)
Cozy First Floor Apartment. Located in a quiet neighborhood.
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!
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (225)
"One of the best properties i've ever stayed at "
The price is AED 536
AED 821 total
includes taxes & fees
2 Dec - 3 Dec
Berkshire Village Carriage House - Super Private!!
Peace and quiet on the lake
Exterior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (198)
"Great trip to Berkshires! Had so much fun. Great property and our dog loved the backyard. We were so happy it was fenced. "
Peace and quiet on the lake
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?
Here 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. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located 14 mi/22.6 km away in Lee. Private patios and fireplaces are included. Easthampton Vacation Rental - Walk to Breweries!: 16.2 mi/26.1 km away in Easthampton. Amenities include sofa beds. Cozy Rustic Apt in 18th c Berkshire Farmhouse: It’s located in Lanesborough, 22 mi/35.3 km from Chester. Includes fireplaces and sofa beds.
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 Berkshire Scenic Railway Museum. In the larger area, you’ll find Pyramid Lake and Jacob’s Pillow.
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.