Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Chesterfield vacation rentals

Fridge, microwave, oven, stovetop

Vacation Home in Holyoke

Cozy Home in Holyoke with 3 bedrooms
9.8 out of 10, Exceptional, (14 reviews)
"Very neat and clean. Decorated for Fall, which was nice. All amenities made for a really nice time."
United States
Stacy G.
The price is ￥20,263
￥51,013 total
includes taxes & fees
Mar 2 - Mar 3
Cozy Home in Holyoke with 3 bedrooms
Interior

Vacation Home in Greenfield

Lovely 2nd Floor Apartment
10.0 out of 10, Exceptional, (49 reviews)
"This is a comfortable and spacious apartment in a great location central to everything in Greenfield. David is also an excellent host who communicated clearly throughout our visit. Would definitely stay here again. "
United States
Geoffrey B.
The price is ￥18,097
￥31,358 total
includes taxes & fees
Mar 5 - Mar 6
Lovely 2nd Floor Apartment
Desk, iron/ironing board, travel crib, WiFi

Vacation Home in Easthampton Ma.

The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, (73 reviews)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
The price is ￥28,057
￥43,875 total
includes taxes & fees
Mar 2 - Mar 3
The Creation Station is a cozy place so make yourself at home.
Exterior detail

Vacation Home in Pittsfield

3-bedroom house in beautiful Berkshires, close to amenities!
The price is ￥28,057
￥47,881 total
includes taxes & fees
Mar 2 - Mar 3
3-bedroom house in beautiful Berkshires, close to amenities!
Property grounds

Vacation Home in Russell

Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is ￥31,174
￥56,676 total
includes taxes & fees
Mar 1 - Mar 2
Big farmhouse in the foothills of the Berkshires
Living area

Cottage in Amherst

Beautiful 2-bedroom cottage on Robert Frost Trail
The price is ￥24,939
￥41,263 total
includes taxes & fees
Feb 28 - Mar 1
Beautiful 2-bedroom cottage on Robert Frost Trail
Smart TV, books

Vacation Home in Sherwood Forest

Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is ￥27,745
￥65,116 total
includes taxes & fees
Mar 16 - Mar 17
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
3 bedrooms, desk, iron/ironing board, travel crib

Vacation Home in Chicopee

Townhouse with Pool Table - Renovated w/ King Bed
10.0 out of 10, Exceptional, (12 reviews)
"Perfect stay for a family. Enjoyed the pool table. Beds were comfortable. Showers were perfect. Beautifully decorated. We felt right at home. Would definitely stay again. "
United States
Tonya Z.
The price is ￥31,174
￥63,838 total
includes taxes & fees
Mar 15 - Mar 16
Townhouse with Pool Table - Renovated w/ King Bed
TV

Apartment in Chicopee

Charming Chicopee Getaway
7.6 out of 10, Good, (4 reviews)
"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. "
United States
Tamara S.
The price is ￥20,107
￥47,300 total
includes taxes & fees
Mar 30 - Mar 31
Charming Chicopee Getaway
Exterior

Apartment in Shelburne Falls

2 Twin beds on 1st floor with En-suite bathroom.
The price is ￥14,340
￥28,030 total
includes taxes & fees
Mar 9 - Mar 10
2 Twin beds on 1st floor with En-suite bathroom.
Property grounds

Cabin in Hinsdale

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is ￥39,816
￥83,193 total
includes taxes & fees
Mar 30 - Mar 31
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Fridge, microwave, oven, stovetop

Apartment in Amherst

Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
9.0 out of 10, Wonderful, (20 reviews)
"Great property! Thank you for a wonderful stay."
United States
David
The price is ￥34,930
￥65,655 total
includes taxes & fees
Mar 6 - Mar 7
Close to Downtown/UMASS Walk-Out Basement Condo with game room & big backyard!
Living area

Apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
10.0 out of 10, Exceptional, (2 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is ￥21,666
￥32,006 total
includes taxes & fees
Mar 8 - Mar 9
Cozy 2-bedroom apartment in Chicopee
Interior

Apartment in Northampton

Button's Modern Luxury Walkup Downtown Northampton
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"
United States
AMY
The price is ￥51,281
￥94,017 total
includes taxes & fees
Mar 4 - Mar 5
Button's Modern Luxury Walkup Downtown Northampton
Fridge, microwave, oven, stovetop

Vacation Home in Colrain

Colrain Spring into Adventure HotTub AirHockey Firepit
9.8 out of 10, Exceptional, (46 reviews)
"Great house for family gatherings "
United Kingdom
John Paul B.
The price is ￥44,150
￥99,808 total
includes taxes & fees
Mar 2 - Mar 3
Colrain Spring into Adventure HotTub AirHockey Firepit
Living area

Apartment in Adams

Penthouse Apartment on Park Street
9.6 out of 10, Exceptional, (14 reviews)
"Clean property, easy check in, and the owner was super communicative. "
United States
Amanda W.
The price is ￥22,601
￥43,527 total
includes taxes & fees
Mar 11 - Mar 12
Penthouse Apartment on Park Street
Exterior

Cabin in Charlemont

Bear Creek Cabin
10.0 out of 10, Exceptional, (46 reviews)
"Beautiful view, very spacious outside and indoors, cozy aesthetic."
United States
Devon I.
The price is ￥62,348
￥93,322 total
includes taxes & fees
Mar 4 - Mar 5
Bear Creek Cabin
Property grounds

Vacation Home in Charlemont

Riverbend Berkshire East Basecamp - 3 bedrooms available
10.0 out of 10, Exceptional, (2 reviews)
"Very nice house and the stay was unproblematic!"
United States
Noah K.
The price is ￥24,939
￥65,813 total
includes taxes & fees
Mar 4 - Mar 5
Riverbend Berkshire East Basecamp - 3 bedrooms available
Terrace/patio

Apartment in Leverett

Terrific 3-bedroom unit in charming Leverett with AC
10.0 out of 10, Exceptional, (1 review)
"The apartment is lovely, so comfortable and quiet!! Caitlin was a wonderful host, very responsive. Would absolutely stay again! "
United States
Anna B.
The price is ￥24,550
￥60,503 total
includes taxes & fees
Mar 9 - Mar 10
Terrific 3-bedroom unit in charming Leverett with AC
Smart TV, books

Vacation Home in Lee

Sun Filled Lenox Retreat - Minutes to Tanglewood!
9.6 out of 10, Exceptional, (4 reviews)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
United States
Paulo I.
The price is ￥28,057
￥71,732 total
includes taxes & fees
Mar 3 - Mar 4
Sun Filled Lenox Retreat - Minutes to Tanglewood!
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 Chesterfield Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Overall pleasant stay; great facilities, staff, and location"
Casey 2-night trip
Posted 3 days ago
Berkshire Mountain Lodge

Find out more about Chesterfield

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Look no further and take a look at our great range of rental properties in Chesterfield!

Frequently asked questions

Can I find vacation rentals in Chesterfield?

Yes, we have vacation rentals near popular attractions in Chesterfield, or you can go with a secluded option if you want a relaxing place to stay. Chesterfield is known for its restaurants and shopping. Make sure you have time to check out the parks while you're in the area.

What are some of the best vacation rentals in Chesterfield?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: Visitors like this Chesterfield vacation home rental. It offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

What’s there to see and do in Chesterfield?

Chesterfield Gorge and Knightville Dam & Reservation are a couple of lovely local spots to get outside and enjoy nature. Chesterfield Public Library and Chesterfield Town Hall are other places to visit while you're in town.

What’s a vacation rental in Chesterfield like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Chesterfield. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family trip or a small group gathering.