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Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Chesterfield vacation rentals

Property grounds

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts

Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
Cummington
The price is AED 400
AED 501 total
includes taxes & fees
22 Jun - 23 Jun
Cozy Escape in a Suite near Bryant Mountain State Forest in Massachusetts
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 AED 479
AED 695 total
includes taxes & fees
23 Jun - 24 Jun
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (55 reviews)
"We really enjoyed your place. It was clean and quiet, with some nice design touches. Beautiful woodwork coming up the stairs!! We used it for a self-crafted meditation retreat."
United States
E Kelly S.
The price is AED 473
AED 799 total
includes taxes & fees
2 Jul - 3 Jul
Lovely 2nd Floor Apartment
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 AED 360
AED 992 total
includes taxes & fees
28 Jun - 29 Jun
Nurse-ready Studio Retreat! 2 Mi to Dtwn Holyoke
Exterior detail

comfort, luxury, privacy

comfort, luxury, privacy
Amherst
9.8 out of 10, Exceptional, (79 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 AED 446
AED 663 total
includes taxes & fees
22 Jun - 23 Jun
comfort, luxury, privacy
Exterior

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

Light-filled treetop apartment close to downtown Greenfield and Highland Park
Greenfield
9.8 out of 10, Exceptional, (6 reviews)
"Nice place"
United States
Tom
The price is AED 780
AED 974 total
includes taxes & fees
22 Jun - 23 Jun
Light-filled treetop apartment close to downtown Greenfield and Highland Park
Property grounds

Cozy Valley View Post & Beam Villa!

Cozy Valley View Post & Beam Villa!
Whately
10.0 out of 10, Exceptional, (9 reviews)
"Thanks for a great stay"
United States
Andrea M.
The price is AED 1,837
AED 2,326 total
includes taxes & fees
22 Jun - 23 Jun
Cozy Valley View Post & Beam Villa!
TV

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is AED 1,172
AED 2,302 total
includes taxes & fees
22 Jun - 23 Jun
Treetop Hideaway in Tyringham
Outdoor dining

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is AED 1,154
AED 2,023 total
includes taxes & fees
23 Jun - 24 Jun
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Fridge, microwave, oven, stovetop

Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
9.8 out of 10, Exceptional, (50 reviews)
"Our 4th week here and our crew could not be happier with the accommodations"
United States
Maureen A.
The price is AED 977
AED 2,285 total
includes taxes & fees
24 Jun - 25 Jun
Spacious 5BR w/ Hot Tub & Games
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, (147 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is AED 698
AED 1,305 total
includes taxes & fees
2 Jul - 3 Jul
Big farmhouse in the foothills of the Berkshires
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 AED 661
AED 1,001 total
includes taxes & fees
22 Jun - 23 Jun
The Creation Station is a cozy place so make yourself at home.
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 AED 595
AED 1,337 total
includes taxes & fees
23 Jun - 24 Jun
Cozy Home in Holyoke with 3 bedrooms
Exterior

Bear Creek Cabin

Bear Creek Cabin
Charlemont
10.0 out of 10, Exceptional, (46 reviews)
"Everything great!"
United States
Andrew P.
The price is AED 1,469
AED 2,195 total
includes taxes & fees
26 Jun - 27 Jun
Bear Creek Cabin
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, (38 reviews)
"Gorgeous place.Great stay.Will diff be backG"
United States
Gerard C.
The price is AED 631
AED 1,591 total
includes taxes & fees
23 Jun - 24 Jun
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior

Rose wisteria 4 guests 2 bedrooms-full+queen beds

Rose wisteria 4 guests 2 bedrooms-full+queen beds
Shelburne Falls
The price is AED 657
AED 1,181 total
includes taxes & fees
25 Jun - 26 Jun
Rose wisteria 4 guests 2 bedrooms-full+queen beds
Fridge, microwave, stovetop, dishwasher

Spacious Holyoke Home: Work, Play & Unwind!

Spacious Holyoke Home: Work, Play & Unwind!
Holyoke
10.0 out of 10, Exceptional, (4 reviews)
"This was a beautiful place to stay and was perfect for our needs. It was very clean and we enjoyed our stay. We didn't realize the house had three separate areas but it worked out well for our dance competition in Springfield."
United States
Celeste D.
The price is AED 2,564
AED 6,701 total
includes taxes & fees
8 Jul - 9 Jul
Spacious Holyoke Home: Work, Play & Unwind!
Smart TV, fireplace, books

5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (4 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is AED 871
AED 2,252 total
includes taxes & fees
23 Jun - 24 Jun
5BR Berkshire Home Mins To The Mountain
Flat-screen TV, books

Cozy First Floor Apartment. Located in a quiet neighborhood.

Cozy First Floor Apartment. Located in a quiet neighborhood.
Chicopee
9.4 out of 10, Exceptional, (8 reviews)
"Perfect spot for UMASS parents' weekend! Just 20ish minutes from campus, super clean, and affordable. Highly recommend!"
United States
Tasha
The price is AED 602
AED 1,096 total
includes taxes & fees
22 Jun - 23 Jun
Cozy First Floor Apartment. Located in a quiet neighborhood.
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, (15 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 AED 883
AED 1,801 total
includes taxes & fees
29 Jun - 30 Jun
Townhouse with Pool Table - Renovated w/ King Bed
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

D. Hotel Suites & Spa

D. Hotel Suites & Spa

10/10 Excellent
"Stay there often. Always a great stay"
Cindy 1-night trip
Posted 1 hour ago
D. Hotel Suites & Spa

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 1-bedroom house in overlooking the river close to downtown Northampton: Visitors like this Chesterfield vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

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. 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.