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Compare 210 Vacation Homes in Chester with updated reviews, rates, and availability.
Cozy apartment located in quiet Williamsburg
Cozy apartment located in quiet Williamsburg
9.8 out of 10, Exceptional, (35)
The price is AED 551
AED 955 total
includes taxes & fees
23 Jun - 24 Jun
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 AED 661
AED 1,030 total
includes taxes & fees
1 Jul - 2 Jul
Private Lake House in the Berkshires
Private Lake House in the Berkshires
9.8 out of 10, Exceptional, (15)
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Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (118)
Tranquil 3-BR Waterfront Retreat
Tranquil 3-BR Waterfront Retreat
10.0 out of 10, Exceptional, (7)
Hearts Desire is a furnished whole house in a small, colorful garden center.
Hearts Desire is a furnished whole house in a small, colorful garden center.
10.0 out of 10, Exceptional, (68)
Massachusetts Vacation Rental w/ Deck
Massachusetts Vacation Rental w/ Deck
9.4 out of 10, Exceptional, (10)
Pristine Home In Becket Woods
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (8)
Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (186)
Chic Pittsfield Home With A View!
Chic Pittsfield Home With A View!
9.0 out of 10, Wonderful, (4)
Beautiful retreat to the woods to enjoy the winter season.
Beautiful retreat to the woods to enjoy the winter season.
10.0 out of 10, Exceptional, (31)
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
8.8 out of 10, Excellent, (3)
Private Access To Laurel Lake, Enjoy Lake Life
Private Access To Laurel Lake, Enjoy Lake Life
10.0 out of 10, Exceptional, (6)
Private Cabin On Over 12 Acres Of Woods!
Private Cabin On Over 12 Acres Of Woods!
9.6 out of 10, Exceptional, (4)
The price is AED 2,828
AED 4,969 total
includes taxes & fees
6 Jul - 7 Jul
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
Hawley Home w/ Deck: 4 Mi to Berkshire East Resort
9.4 out of 10, Exceptional, (3)
4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee
4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (206)
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, (21)
Stockbridge Home, Come Experience The Berkshires!
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (12)
Peaceful, Post and Beam Loft, Sleeps 9
Peaceful, Post and Beam Loft, Sleeps 9
10.0 out of 10, Exceptional, (8)
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 property types in Chester
Cozy Berkshires Vacation Rental Near Hiking!
Cozy Berkshires Vacation Rental Near Hiking!
Cozy apartment located in quiet Williamsburg
Cozy apartment located in quiet Williamsburg
9.8 out of 10, Exceptional, (35)
The price is AED 551
AED 955 total
includes taxes & fees
23 Jun - 24 Jun
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)
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 Chester hotelsExpedia verified reviews
![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel](http://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27_y.jpg)
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
5/5 Excellent
"We enjoyed our stay, played mini golf, swam and used the arcade. There were a lot of activities and amenities to choose from. Well kept property. "
A verified traveler stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
Posted 16 hours ago
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