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Compare 42 Apartments in Chesterfield 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
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
comfort, luxury, privacy
comfy king size bed

comfort, luxury, privacy

9.8 out of 10, Exceptional, (56)
"Great place to stay when visiting your student! Good for 1-3 people. Highly recommend!"
The price is AED 496
AED 718 total
includes taxes & fees
27 Nov - 28 Nov
comfort, luxury, privacy
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
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
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Interior

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2.0 star property
10.0 out of 10, Exceptional, (3)
"The property was clean, well equipped, and very comfortable. We had ample parking for our car and our son's car right outside the door, with room for our other son to park when he visited us. It is beautifully decorated with paintings and art objects, many with an Asian theme. It's close to the Shelburne Falls village and to Route 2 for touring the area, but it was very quiet at night, lending itself to very restful sleeps over night. Host was very available and helpful! Hope to stay there...
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Sweet suite in Montague near the canal and downtown Turners Falls.
Room

Sweet suite in Montague near the canal and downtown Turners Falls.

2.0 star property
9.4 out of 10, Exceptional, (3)
"The location of this space was perfect, only a mile from our family’s location. The first floor apartment provided more than adequate room for us to refresh, recharge, and rest during our one week’s stay in the area. The queen sized bed was incredibly comfortable, while the oversized closet provided more than enough room for clothes and personal effects. The Keurig machine was delightful to brew hot tea and coffee. The pull out sofa provided additional space for snoozing. Overall, a very...
Sweet suite in Montague near the canal and downtown Turners Falls.
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!
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 382
AED 896 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 793 total
includes taxes & fees
27 Nov - 28 Nov
Charming Apt in 18th c Berkshire Farmhouse
Quiet Neighborhood, For Bird Lovers
Property grounds

Quiet Neighborhood, For Bird Lovers

10.0 out of 10, Exceptional, (45)
"We stayed here while visiting our daughter, a student at UMass-Amherst, last year and liked it so much, we stayed again this year. Lovely place! Quiet neighborhood, great host (who even leaves fresh food staples in the fridge for her guests), very clean and well maintained. Two thumbs up!"
Quiet Neighborhood, For Bird Lovers
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.
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

6.0 out of 10, (3)
"I had a really nice stay here with my dog. It was clean, comfortable and a nice little well equipped apartment in a great neighborhood. The Wi-Fi was excellent for work and super fast. The bed was so comfortable. The kitchen was really nice and I enjoyed the coffee maker and wall mounted TV and it looked like a new couch, which was very comfortable too. The bathroom not only had a good shower with great hot water and pressure. There was a big bathtub. Towels and linens were clean and plentiful....
Free coffee a comfortable bed food and drinks
Bright Boho Apt in 18th c Berkshire Farmhouse

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 AED 635
AED 926 total
includes taxes & fees
1 Dec - 2 Dec
Bright Boho Apt in 18th c Berkshire Farmhouse
Convenient pet friendly 2br/3bd w/ full bathroom located in a safe & quite city
Room

Convenient pet friendly 2br/3bd w/ full bathroom located in a safe & quite city

10.0 out of 10, Exceptional, (1)
"The host was very friendly and available."
Convenient pet friendly 2br/3bd w/ full bathroom located in a safe & quite city
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 Chesterfield

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
Pristine Home In Becket Woods

Pristine Home In Becket Woods

10.0 out of 10, Exceptional, (13)
"Pristine can mean several different things. My interpretation was to be “like new”. This dwelling did not quite live up to that standard, but was clean, sans the “mud room” and what appeared to be mold on the peak of the ceiling above the living room. The original listing stated firewood was provided by the host. Then, the checkin instructions stated guests provided their own. Not huge, just misstated in the listing (since changed). There was a power outage while we were there, thus no...
Pristine Home In Becket Woods
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 Chesterfield?
You might not have many choices within the heart of Chesterfield, but Expedia can help you locate accommodations within the larger area with similar amenities to an apartment. When you search for a place to stay on Expedia, you can use the filters to search for conveniences you might find in an apartment like a kitchen. You can also filter by similar property types like vacation homes, condos, or guest houses.
Why choose an apartment over a traditional hotel room?
Often offering more space than a traditional hotel room, an apartment includes a kitchen for convenient home-cooked meals. Apartments are ideal for families who want the conveniences of home but also for solo travelers who want to stay in at night and plan out their next day.
What's the top apartment I should consider for a stay in Chesterfield?
Below are some of the favorite apartments in the area to choose from: Elm Suite with a Private Bathroom in front of Smith College Quadrangle: Located in Northampton, 11.2 mi/18.1 km from the heart of Chesterfield. Includes jetted bathtubs. Access to a spa tub is available on site. Easthampton Vacation Rental - Walk to Breweries!: It’s situated in Easthampton, 12.1 mi/19.5 km away. Includes sofa beds. Comfort, luxury, privacy: Located 17 mi/27.3 km away in Amherst. Private yards and Smart TVs are included. Access to a spa tub is available on site. Cozy Berkshires Vacation Rental Near Hiking!: Located in Chester, 10.5 mi/16.9 km from Chesterfield. Includes sofa beds. Access to a game room is available on site.
What will the weather be like when I travel to Chesterfield?
Though weather is just one factor, it can really affect your travel plans, especially if you are planning a longer stay in Chesterfield. The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 30°F. The snowiest months in Chesterfield are January, February, November, and March, with each month seeing an average of 6 inches of snowfall.
What are the must-see places to visit in Chesterfield?
Chesterfield Gorge and Knightville Dam & Reservation are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Chesterfield Town Hall and Westfield River.
What's the best way to get to and around Chesterfield?
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 16.6 mi (26.8 km) from the heart of the city. You can also search for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 23.2 mi (37.3 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.