Photo by Elizabeth Massa Peroulakis
Chester Vacation Rentals
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Vacation Rentals in Chester
Cozy Berkshires Vacation Rental Near Hiking!
Cozy Berkshires Vacation Rental Near Hiking!
Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (184)
Cozy apartment located in quiet Williamsburg
Cozy apartment located in quiet Williamsburg
9.8 out of 10, Exceptional, (33)
The price is ¥23,513
per night
May 29 - May 30
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Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
Easthampton Vacation Rental - Walk to Breweries!
Easthampton Vacation Rental - Walk to Breweries!
10.0 out of 10, Exceptional, (2)
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (195)
Pristine Home In Becket Woods
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (7)
Big farmhouse in the foothills of the Berkshires
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (120)
The price is ¥30,617
per night
Jun 24 - Jun 25
Serene Acreage - Pond - Hiking Trails Nearby
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (4)
The Creation Station is a cozy place so make yourself at home.
The Creation Station is a cozy place so make yourself at home.
10.0 out of 10, Exceptional, (52)
The price is ¥25,122
per night
May 27 - May 28
Fox Hollow Luxury Ranch Laurel Lake
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, (2)
Private Island - Largest Fresh Water Reservoir in Mass....
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, (3)
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (203)
The Meadows House @ Otis Ridge w/ 7-person hot tub
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, (20)
Quintessential 6-BR Berkshires Lodge
Quintessential 6-BR Berkshires Lodge
10.0 out of 10, Exceptional, (4)
Charming historic cottage on scenic road to Mt. Greylock
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (94)
Secluded Cabin On Acres Of Woods Lake Access
Secluded Cabin On Acres Of Woods Lake Access
10.0 out of 10, Exceptional, (3)
Rockspring by AvantStay | Huge Berkshires Estate
Rockspring by AvantStay | Huge Berkshires Estate
8.8 out of 10, Excellent, (10)
Berkshires Cabin 2 Mi to Appalachian Trail!
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (6)
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.
Other types of properties in Chester you may be interested in
Quality Inn West Springfield
Quality Inn West Springfield
7.2 out of 10, Good, (1002)
The price is ¥15,114
per night
Jun 4 - Jun 5
D. Hotel Suites & Spa
D. Hotel Suites & Spa
9.4 out of 10, Exceptional, (2272)
The price is ¥23,708
per night
May 27 - May 28
La Quinta Inn & Suites by Wyndham Springfield MA
La Quinta Inn & Suites by Wyndham Springfield MA
8.2 out of 10, Very Good, (1260)
The price is ¥19,155
per night
May 30 - May 31
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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Frequently asked questions
Recent reviews of Chester propertiesExpedia verified reviews
5/5 Excellent
"It was clean and I liked the decor. The place had character. Breakfast was good too."
A verified traveler stayed at The Ellery
Posted 18 hours ago