Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Chesterfield vacation rentals

Apartment (0 Bedroom) | Interior

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
3.0 star property
Holyoke
The price is ￥18,314
￥46,025 total
includes taxes & fees
Jun 14 - Jun 15
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (55 reviews)
"Beautifully appointed and comfortable. "
United States
Emily Kate G.
The price is ￥20,543
￥34,331 total
includes taxes & fees
Jun 15 - Jun 16
Lovely 2nd Floor Apartment
1 bedroom, desk, iron/ironing board, travel crib

The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (75 reviews)
"Host was very accommodating."
United States
Christopher K.
The price is ￥28,665
￥43,225 total
includes taxes & fees
Jun 1 - Jun 2
The Creation Station is a cozy place so make yourself at home.
Smart TV

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Amherst
9.8 out of 10, Exceptional, (111 reviews)
"Lovely place to stay and close to a nice cafe/market. Hosts were friendly and had fresh breakfast food in the refrigerator waiting for us. "
United States
Bill K.
The price is ￥20,782
￥30,329 total
includes taxes & fees
May 31 - Jun 1
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Fridge, microwave, oven, stovetop

Cozy Home in Holyoke with 3 bedrooms

Cozy Home in Holyoke with 3 bedrooms
Holyoke
9.8 out of 10, Exceptional, (17 reviews)
"The house was lovely and clean and the location was very convenient for us. We would stay there again!"
United States
Jennifer S.
The price is ￥26,436
￥58,880 total
includes taxes & fees
Jun 1 - Jun 2
Cozy Home in Holyoke with 3 bedrooms
Exterior

Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke

Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
Holyoke
10.0 out of 10, Exceptional, (2 reviews)
"The studio was clean, new and modern. There are no windows so it was dark and quiet to sleep. "
United States
Michelle
The price is ￥15,288
￥44,987 total
includes taxes & fees
Jun 9 - Jun 10
Nurse-Ready Studio Retreat! 2 Mi to Dtwn Holyoke
Exterior detail

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Greenfield
9.6 out of 10, Exceptional, (8 reviews)
"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."
United States
Andrew R.
The price is ￥19,349
￥44,560 total
includes taxes & fees
May 31 - Jun 1
Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires
Exterior

Rose room Victorian home queen bed private bath

Rose room Victorian home queen bed private bath
Shelburne Falls
The price is ￥16,482
￥30,684 total
includes taxes & fees
Jun 1 - Jun 2
Rose room Victorian home queen bed private bath
3 bedrooms, desk, iron/ironing board, travel crib

Townhouse with Pool Table - Renovated w/ King Bed

Townhouse with Pool Table - Renovated w/ King Bed
Chicopee
10.0 out of 10, Exceptional, (16 reviews)
"The house was clean, comfortable and had everything covered for the weekend. A must stay when traveling to Chicopee."
United States
RAFAEL U.
The price is ￥32,678
￥70,317 total
includes taxes & fees
Jun 1 - Jun 2
Townhouse with Pool Table - Renovated w/ King Bed
Fridge, microwave, oven, stovetop

Quaint 2-bedroom apartment close to UMass Amherst great neighborhood in Holyoke

Quaint 2-bedroom apartment close to UMass Amherst great neighborhood in Holyoke
Holyoke
The price is ￥22,215
￥38,511 total
includes taxes & fees
May 31 - Jun 1
Quaint 2-bedroom apartment close to UMass Amherst great neighborhood in Holyoke
Exterior

Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is ￥19,110
￥33,619 total
includes taxes & fees
Jun 1 - Jun 2
Private bed with En-suite bathroom Marigold Room
Exterior detail

comfort, luxury, privacy

comfort, luxury, privacy
Amherst
9.8 out of 10, Exceptional, (78 reviews)
"We have stayed here several times and it is always perfect. The hosts are great and the house is perfect. "
United States
paul s.
The price is ￥19,349
￥28,729 total
includes taxes & fees
Jun 4 - Jun 5
comfort, luxury, privacy
Outdoor spa tub

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ￥25,512
￥61,049 total
includes taxes & fees
May 31 - Jun 1
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Exterior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is ￥8,743
￥46,764 total
includes taxes & fees
Jun 7 - Jun 8
Real Estate: Therapy - Lake, Laundry, Love it
Property grounds

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (36 reviews)
"Gorgeous place.Great stay.Will diff be backG"
United States
Gerard C.
The price is ￥28,522
￥70,460 total
includes taxes & fees
Jun 1 - Jun 2
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Interior

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥23,219
￥59,912 total
includes taxes & fees
Jun 1 - Jun 2
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Exterior

Light-filled treetop apartment close to downtown Greenfield and Highland Park

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
9.6 out of 10, Exceptional, (5 reviews)
"Nice place"
United States
Tom
The price is ￥35,831
￥44,649 total
includes taxes & fees
Jun 17 - Jun 18
Light-filled treetop apartment close to downtown Greenfield and Highland Park
Property grounds

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (146 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is ￥31,850
￥57,905 total
includes taxes & fees
Jun 7 - Jun 8
Big farmhouse in the foothills of the Berkshires
Living area

Cozy 2-bedroom apartment in Chicopee

Cozy 2-bedroom apartment in Chicopee
Chicopee
10.0 out of 10, Exceptional, (6 reviews)
"nice cozy home in a quiet neighborhood. easy access to highways. would stay here again. "
United States
Christopher P.
The price is ￥25,483
￥36,500 total
includes taxes & fees
Jun 2 - Jun 3
Cozy 2-bedroom apartment in Chicopee
Interior

Button's Modern Luxury Walkup Downtown Northampton

Button's Modern Luxury Walkup Downtown Northampton
Northampton
10.0 out of 10, Exceptional, (4 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 ￥37,723
￥77,712 total
includes taxes & fees
Jun 2 - Jun 3
Button's Modern Luxury Walkup Downtown Northampton
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

Tru by Hilton Chicopee Springfield

Tru by Hilton Chicopee Springfield

8/10 Good
"Night bangs outside room"
Tamara 2-night trip
Posted 1 hour ago
Tru by Hilton Chicopee Springfield

Find out more about Chesterfield

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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?

Peace and quiet on the lake: Visitors like this Chesterfield vacation home rental. It is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

What’s there to see and do in Chesterfield?

Chesterfield Gorge and Westfield River are a couple of lovely local spots to get outside and enjoy nature. Silvio O. Conte National Fish and Wildlife Refuge and Chesterfield Public Library 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.