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  1. World
  2. >North America
  3. >United States
  4. >Massachusetts
  5. >Hampden
  6. >Chester

Hotels in Chester

200+ HOTELS IN AND AROUND CHESTERRanking can be influenced by the commissions we receive.
Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts main photo
Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts
Vacation Home in Chester MAUS flag
9.2
Excellent
$
+1
Info
Categories
Parking
19 more hotels nearby!
Pristine Home In Becket Woods main photo
Pristine Home In Becket Woods
2.3 mi from Chester
Vacation Home in Becket MAUS flag
$
+4
Info
Categories
Ski
Dog Friendly
Free Wi-Fi
Becket Motel main photo
Becket Motel
4.2 mi from Chester
Motel in Becket Center MAUS flag
2.8
Rated
Currently inactive on our platform.
$
+4
Info
Categories
Ski
Free Wi-Fi
Parking
Historic Huntington Home - Walk to Westfield River main photo
Historic Huntington Home - Walk to Westfield River
4.5 mi from Chester
Vacation Home in Huntington MAUS flag
From $339
$
+3
Info
Categories
Ski
Free Wi-Fi
Parking
Lakes & Leisure! Spacious Berkshire Getaway main photo
Lakes & Leisure! Spacious Berkshire Getaway
5.0 mi from Chester
Vacation Home in Becket MAUS flag
Currently inactive on our platform.
$
+1
Info
Categories
Parking
Serene and Historic Farmhouse in the Berkshires main photo
Serene and Historic Farmhouse in the Berkshires
5.0 mi from Chester
Vacation Home in Hinsdale MAUS flag
$
+2
Info
Categories
Dog Friendly
Parking
Becket Home w/ 3-Season Porch: Walk to Lake Access main photo
Becket Home w/ 3-Season Porch: Walk to Lake Access
5.1 mi from Chester
Vacation Home in Becket MAUS flag
8.0
Very Good
$
+2
Info
Categories
Free Wi-Fi
Parking
A-Frame Cabin w/ Furnished Deck in Becket! main photo
A-Frame Cabin w/ Furnished Deck in Becket!
6.3 mi from Chester
Vacation Home in Becket MAUS flag
6.5
Rated
$
+4
Info
Categories
Ski
Dog Friendly
Free Wi-Fi
Little Longbow Lakefront Chalet main photo
Little Longbow Lakefront Chalet
6.5 mi from Chester
Vacation Home in Becket MAUS flag
9.0
Excellent
$
+2
Info
Categories
Free Wi-Fi
Parking
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits! main photo
Berkshires Home on 11 Acres w/ Pond & 2 Fire Pits!
6.5 mi from Chester
Vacation Home in Becket MAUS flag
$
+3
Info
Categories
Ski
Free Wi-Fi
Parking
Berkshires Modern Cottage - Sauna & EV Charger main photo
Berkshires Modern Cottage - Sauna & EV Charger
6.6 mi from Chester
Vacation Home in Huntington MAUS flag
$
+3
Info
Categories
Parking
EV charging stations
Free Wi-Fi
Quiet Cabin On Over 12 Acres Of Woods! main photo
Quiet Cabin On Over 12 Acres Of Woods!
7.0 mi from Chester
Vacation Home in Becket MAUS flag
9.0
Excellent
Currently inactive on our platform.
$
+5
Info
Categories
Ski
Dog Friendly
Free Wi-Fi
Charming Cabin Getaway with a Wood-Burning Stove in Chesterfield, Massachusetts main photo
Charming Cabin Getaway with a Wood-Burning Stove in Chesterfield, Massachusetts
7.8 mi from Chester
Vacation Home in South Worthington MAUS flag
$
Info
The Glow Room at Indian Hollow main photo
The Glow Room at Indian Hollow
7.9 mi from Chester
Vacation Home in South Worthington MAUS flag
Currently inactive on our platform.
$
Info
Categories
Parking
Berkshire Winter Chalet Sauna, ski & Fireplace main photo
Berkshire Winter Chalet Sauna, ski & Fireplace
8.1 mi from Chester
Chalet in Otis MAUS flag
9.3
Excellent
From $537
$
+4
Info
Categories
Ski
Free Wi-Fi
Parking
Serene Berkshires Home On 5 Acres, Rustic & Chic main photo
Serene Berkshires Home On 5 Acres, Rustic & Chic
8.7 mi from Chester
Vacation Home in Otis MAUS flag
$
+5
Info
Categories
Ski
Dog Friendly
Free Wi-Fi
Imaginative Octogonal Glass Treehouse on Seven Private Acres near Great Barrington, MA main photo
Imaginative Octogonal Glass Treehouse on Seven Private Acres near Great Barrington, MA
8.8 mi from Chester
Vacation Home in Great Barrington MAUS flag
Currently inactive on our platform.
$
Info
Peaceful Cabin Close to Skiing and Hiking main photo
Peaceful Cabin Close to Skiing and Hiking
9.1 mi from Chester
Vacation Home in Otis MAUS flag
9.0
Excellent
From $331
$
+3
Info
Categories
Ski
Free Wi-Fi
Parking
East Otis Reservoir Cabin w/ Porch - Walk to Lake! main photo
East Otis Reservoir Cabin w/ Porch - Walk to Lake!
9.4 mi from Chester
Vacation Home in East Otis MAUS flag
From $211
$
+3
Info
Categories
Ski
Dog Friendly
Parking
Berkshire Lake Lodge main photo
Berkshire Lake Lodge
9.4 mi from Chester
Motel in Becket MAUS flag
9.2
Excellent
$
+3
Info
Categories
Free Wi-Fi
Parking
Small
*Additional taxes or fees may apply. Please check the final price before completing your booking.Showing 1-20 out of 200+ hotels in and around Chester
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