Chesterfield Vacation Rentals
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Chesterfield vacation homes
5.4 out of 10, (852 reviews)
"Some of the furniture and rugs show age. The bed was comfortable and the staff was always available to help!"
DAVID
The price is CA $88
CA $98 total
includes taxes & fees
Jul 15 - Jul 16
8.6 out of 10, Excellent, (187 reviews)
"It's a really nice place to stay!"
Vidita
The price is CA $173
CA $194 total
includes taxes & fees
Jul 15 - Jul 16
10.0 out of 10, Exceptional, (3 reviews)
"We thoroughly enjoyed all aspects of our stay. The Inn was incredibly charming and comfortable. We will definitely be back."
Dan
The price is CA $333
CA $433 total
includes taxes & fees
Jul 15 - Jul 16
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
9.4 out of 10, Exceptional, (133 reviews)
"Breakfast was good, good location, friendly staff."
Courtney
The price is CA $199
CA $223 total
includes taxes & fees
Jul 22 - Jul 23
Red Roof Inn PLUS+ South Deerfield – Amherst
Red Roof Inn PLUS+ South Deerfield – AmherstSouth Deerfield
7.2 out of 10, Good, (1,012 reviews)
"Clean and convenient!"
Katie
The price is CA $137
CA $153 total
includes taxes & fees
Jul 19 - Jul 20
9.0 out of 10, Wonderful, (36 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
James
The price is CA $234
CA $262 total
includes taxes & fees
Jul 15 - Jul 16
8.4 out of 10, Very good, (1,014 reviews)
"Great place"
Michelle
The price is CA $187
CA $209 total
includes taxes & fees
Jul 19 - Jul 20
7.2 out of 10, Good, (961 reviews)
"The coffee was fantastic. Rooms were quiet"
Richard
The price is CA $138
CA $155 total
includes taxes & fees
Aug 6 - Aug 7
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.
Find vacation rentals that suit your style
Cabins
Private vacation homes
Save an average of 15% on thousands of hotels when you're signed in
Top Chesterfield Hotel Reviews
Berkshire Mountain Lodge
10/10 Excellent
Find out more about Chesterfield
Chesterfield Vacation Homes information
Number of reviews | 13,951 |
|---|---|
Accommodation | 152 Vacation Homes |
Lowest Price | CA $98 |
Highest Price | CA $433 |
Explore a world of travel with Expedia
- Hotels near Bridge of Flowers
- Homewood Suites by Hilton Holyoke
- Inn on Boltwood
- Cheap Hotels in Holyoke
- South Deerfield Hotels
- Hotels near Deerfield Academy
- B&B in Florida
- Motels in Shelburne
- Hampton Inn Hadley
- Rv Parks in Leyden
- Cabin Rentals in Chicopee
- Villas in Beartown State Forest
- B&B in Haydenville
- West Hatfield Hotels
- Resorts in Lenox
- Cabin Rentals in South Amherst
- Springfield Hotels
- Northampton Hotels
- Charlemont Hotels
- Hotels near Mullins Center
- Pet-Friendly Hotels in Western Massachusetts
- B&B in Russell
- Motels in Greenfield
- Guest Houses in Gill
- Cabin Rentals in Savoy
- Shelburne Falls Hotels
- Historic 1804 house in N Becket Village in the Berkshires
- Plainfield Hotels
- Florence Hotels
- Chalets in Monroe
- D. Hotel Suites & Spa
- Condo Rentals in Granby
- Apartments in Huntington
- The Ellery
- Hotels with Kitchenettes in Western Massachusetts
- Chalets in Becket
- Spa Hotels in Northampton
- B&B in Adams
- Cheap Hotels in Amherst
- Hotel UMass
- Deerfield Hotels
- Hotel Northampton
- Hotels with Hot Tubs in Western Massachusetts
- Condo Rentals in Florida
- Resorts in The Berkshires
- Holyoke Hotels
- Fairfield Inn & Suites Springfield Holyoke
- Hotels near Berkshire East Ski Resort
- B&B in Hadley
- Amherst Hotels
- B&B in Lee
- South Hadley Hotels
- Hostels in Springfield
- Wyndham Hotels in Holyoke
- Condo Rentals in Otis
- Comfort Inn & Suites Hadley
- Oceanfront Hotels in Western Massachusetts
- Hotels near University of Massachusetts Amherst
- Hadley Hotels
- Haydenville Hotels
- Cottages in The Berkshires
- Hotels with a Pool in Western Massachusetts
- Cabin Rentals in Granby
- Becket Hotels
- Old Mill Inn
- Cabin Rentals in Westfield
- Motels in Granville
- Hotels with a Lazy River in Western Massachusetts
- Apartments in Cheshire
- Hotels with an Indoor Pool in Western Massachusetts
- Easthampton Hotels
- Southampton Hotels
- Daniel Stebbins House
- Williamsburg Hotels
- Courtyard by Marriott Hadley Amherst
- Cabin Rentals in Amherst
- Washington Hotels
- Ashfield Hotels
- Chalets in Western Massachusetts
- Flights to Hadley
- Flights from Northampton
- Flights to Deerfield
- Flights to Western Massachusetts
- Flights from Becket
- Flights from Toronto (YYZ) to Westfield (BAF)
- Flights to Northampton
- Flights from Windsor
- Flights from Holyoke
- Flights to Easthampton
- Flights to Amherst
- Flights to Williamsburg
- Flights to Springfield