Search Cottages in Chesterfield
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check availability on Cottages in Chesterfield
Compare 41 Cottages in Chesterfield with updated reviews, rates, and availability.
Private Island - Largest Fresh Water Reservoir in Mass....
Private Island - Largest Fresh Water Reservoir in Mass....
9.0 out of 10, Wonderful, (7)
East Otis Vacation Rental w/ Private Deck & BBQ!
East Otis Vacation Rental w/ Private Deck & BBQ!
9.6 out of 10, Exceptional, (7)
Massachusetts Vacation Rental w/ Deck
Massachusetts Vacation Rental w/ Deck
Charming historic cottage on scenic road to Mt. Greylock
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (104)
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
6.0 out of 10, (1)
Spacious Historic Home in the Berkshires!
Spacious Historic Home in the Berkshires!
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Charlemont Retreat on Chickley River w/ EV Charger
Charlemont Retreat on Chickley River w/ EV Charger
10.0 out of 10, Exceptional, (1)
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Chesterfield
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (225)
The price is AED 536
AED 821 total
includes taxes & fees
2 Dec - 3 Dec
Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (198)
Pristine Home In Becket Woods
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (13)
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.
Recent reviews of Chesterfield hotels
Recent reviews of Chesterfield hotels
5/5 Excellent
"The restaurant is as great!"
A verified traveler stayed at Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Posted 1 day ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Top Cottages in Other Destinations
More Accommodation Types in Chesterfield
- Vacation Homes in Chesterfield
- Apartments in Chesterfield
- Cabin Rentals in Chesterfield
- Motels in Chesterfield
- Farmstay in Chesterfield
- B&B in Chesterfield
- Guest Houses in Chesterfield
- Chalets in Chesterfield
- Condo Rentals in Chesterfield
- Resorts in Chesterfield
- Lodges in Chesterfield
- Villas in Chesterfield
- Hotels