Travelmyth Logo
7,258,491 hotelsin 60 categories
Sign In
ParkingFree Wi-FiSkiDog FriendlyPoolAccessibleSmall3 StarBusinessGymHoneymoonFamilyOutdoor PoolIndoor PoolAdult OnlySustainability Journey4 StarHeated PoolEV charging stationsLuxuryGolfRooms with FireplaceTennisSki In Ski OutPrivate PoolRomanticHistoricBoutique-Style5 StarPool Lap LanesSpaPool Water SlideRooms with Jacuzzi / Hot-TubHealth & SafetyHauntedDogs Stay FreeYoga
  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
9.3
Excellent
$
+2
Info
Categories
Dog Friendly
Parking
19 more hotels nearby!
Berkshire Vacation Rentals: Pristine Home In Becket Woods main photo
Berkshire Vacation Rentals: Pristine Home In Becket Woods
2.3 mi from Chester
Vacation Home in Becket MAUS flag
0.0
$
+5
Info
Categories
Ski
Dog Friendly
Free Wi-Fi
The becket Motel main photo
The becket Motel
4.2 mi from Chester
Motel in Becket Center MAUS flag
3.3
Rated
From $116
$
+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
0.0
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
0.0
$
+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
0.0
$
+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
0.0
$
+3
Info
Categories
Ski
Free Wi-Fi
Parking
Berkshire Vacation Rentals: Private Cabin On Over 12 Acres Of Woods main photo
Berkshire Vacation Rentals: Private Cabin On Over 12 Acres Of Woods
7.0 mi from Chester
Vacation Home in Becket MAUS flag
9.0
Excellent
$
+5
Info
Categories
Ski
Dog Friendly
Free Wi-Fi
The Retreat At Norwich Lake main photo
The Retreat At Norwich Lake
7.3 mi from Chester
Lodge in Huntington MAUS flag
9.1
Excellent
Currently inactive on our platform.
$
+4
Info
Categories
Parking
3 Star
Ski
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
0.0
$
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
0.0
Currently inactive on our platform.
$
Info
Categories
Parking
Berkshire Fall Chalet Sauna, Lake & Firepit main photo
Berkshire Fall Chalet Sauna, Lake & Firepit
8.1 mi from Chester
Chalet in Otis MAUS flag
9.3
Excellent
From $538
$
+4
Info
Categories
Ski
Free Wi-Fi
Parking
Home in the Woods main photo
Home in the Woods
8.7 mi from Chester
Vacation Home in Westfield MAUS flag
8.0
Very Good
Currently inactive on our platform.
$
+2
Info
Categories
Free Wi-Fi
Parking
Private Berkshires Home On 5+ Acres Rustic & Chic main photo
Private Berkshires Home On 5+ Acres Rustic & Chic
8.7 mi from Chester
Vacation Home in Otis MAUS flag
0.0
$
+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
0.0
Currently inactive on our platform.
$
Info
Berkshires Cabin 2 Mi to Appalachian Trail! main photo
Berkshires Cabin 2 Mi to Appalachian Trail!
9.1 mi from Chester
Vacation Home in Otis MAUS flag
9.0
Excellent
From $332
$
+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
0.0
From $213
$
+3
Info
Categories
Ski
Dog Friendly
Parking
*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
Save more on the App
Popular destinations users search for:
Hotels in LondonHotels in ManchesterHotels in EdinburghHotels in BlackpoolHotels in YorkHotels in LiverpoolHotels in Brighton & HoveHotels in Lake DistrictHotels in CardiffHotels in BirminghamHotels in GlasgowHotels in BelfastHotels in BournemouthHotels in BathHotels in DubaiHotels in ParisHotels in BristolHotels in DublinHotels in LeedsHotels in AmsterdamHotels in ChesterHotels in EastbourneHotels in SantoriniHotels in TenerifeHotels in KeswickHotels in IstanbulHotels in BradfordHotels in CarlisleHotels in WorcesterHotels in GreenwichHotels in RyeHotels in SingaporeHotels in DonegalHotels in PhuketHotels in PositanoHotels in FaroHotels in FalmouthHotels in AlbufeiraHotels in AngleseyHotels in CyprusHotels in OsloHotels in Royal Tunbridge WellsHotels in TelfordHotels in BarryHotels in WarringtonHotels in PollensaHotels in SpainHotels in Zakynthos
Categories
Map
7,258,491
Hotels
60
Categories
49,804
Regions
208,995
Cities
Featured popular searches
Hotels with EV Charging Stations in Lake District
Accessible Hotels in Lake District
Hotels with Pool in Scotland
Hotels near Golf Courses in England
Hotels for Honeymoon in Ireland
Boutique-style Hotels in Nottingham
Family Friendly Hotels in Croatia
Hotels with Parking in Newcastle upon Tyne
4-Star Hotels in Albufeira
Historic Hotels in Amsterdam
Luxury Hotels in Iceland
Hotels in Cotswolds
Former Castle Hotels in Durham
Small Hotels in Marrakech
Spa Hotels in France
5-Star Hotels in Lytham St Annes
3-Star Hotels in Madagascar
Dog Friendly Hotels in Penzance
Romantic Hotels in Port Stephens
4-Star Hotels in Riga
Hotel Bristol
Hotel Nineteen
Elia Estia
Cheap Hotels in Warrington