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  1. World
  2. >North America
  3. >United States
  4. >Massachusetts
  5. >Berkshire
  6. >Pittsfield

Small Hotels in Pittsfield

61 HOTELS IN AND AROUND PITTSFIELDRanking can be influenced by the commissions we receive.
Heart of the Berkshires Motel main photo
Heart of the Berkshires Motel
Motel in Pittsfield MAUS flag
7.3
Good
From $98
$
+6
Info
Categories
Small
Ski
Sustainability Journey
19 more hotels nearby!
Weathervane Motel Lanesboro main photo
Weathervane Motel Lanesboro
4.0 km from Pittsfield
Motel in Lanesborough MAUS flag
6.2
Rated
From $84
$
+3
Info
Categories
Small
Ski
Free Wi-Fi
The Dewey by The Lenox Collection main photo
The Dewey by The Lenox Collection
6.0 km from Pittsfield
Bed & Breakfast in Lenox MAUS flag
7.0
Good
From $135
$
+4
Info
Categories
Small
Ski
Parking
EV charging stations
Whistler's Inn main photo
Whistler's Inn
6.0 km from Pittsfield
Bed & Breakfast in Lenox MAUS flag
8.3
Very Good
From $165
$
+3
Small
Known for its elegant décor and tranquil atmosphere, Whistler's Inn offers a relaxing retreat in Lenox. The focus on comfort and personalized service ensures a memorable stay for guests seeking a cozy and intimate experience.
Garden Gables main photo
Garden Gables
6.1 km from Pittsfield
Hotel in Lenox MAUS flag
0.0
$
+4
Info
Categories
Small
Free Wi-Fi
Parking
The Inn at Richmond main photo
The Inn at Richmond
6.2 km from Pittsfield
Inn in Richmond MAUS flag
9.7
Excellent
From $382
$
+2
Info
Categories
Small
Ski
33 Main main photo
33 Main
6.3 km from Pittsfield
Inn in Lenox MAUS flag
8.8
Excellent
From $391
$
+4
Small
Located in the heart of Lenox, 33 Main offers comfortable and stylish accommodations. The inn's central location provides easy access to the town's attractions, making it a convenient and charming choice for a Berkshires getaway.
Doctor Sax House main photo
Doctor Sax House
6.4 km from Pittsfield
Hotel in Lenox MAUS flag
9.0
Excellent
$
+2
Info
Categories
Small
Dog Friendly
Parking
Gateways Inn main photo
Gateways Inn
6.4 km from Pittsfield
Bed & Breakfast in Lenox MAUS flag
9.4
Excellent
From $241
$
+4
Info
Categories
Small
Parking
EV charging stations
Ski
Hampton Terrace Inn main photo
Hampton Terrace Inn
6.5 km from Pittsfield
Hotel in Lenox MAUS flag
9.4
Excellent
From $306
$
+6
Small
This inn offers luxurious accommodations and personalized service, ensuring a memorable stay. The beautiful gardens and central location in Lenox make it a perfect base for exploring the Berkshires' cultural attractions.
Brook Farm Inn main photo
Brook Farm Inn
6.8 km from Pittsfield
Bed & Breakfast in Lenox MAUS flag
9.3
Excellent
From $217
$
+6
Small
Known for its literary and artistic ambiance, Brook Farm Inn provides a tranquil retreat with comfortable rooms and a focus on relaxation. Its location in Lenox makes it ideal for exploring the cultural attractions of the Berkshires.
Eastgate Inn B&B main photo
Eastgate Inn B&B
6.9 km from Pittsfield
Bed & Breakfast in Lenox MAUS flag
9.5
Excellent
From $197
$
+3
Info
Categories
Small
Ski
Parking
Eastgate Inn B&B main photo
Eastgate Inn B&B
6.9 km from Pittsfield
Bed & Breakfast in Lenox MAUS flag
9.8
Excellent
From $197
$
+4
Info
Categories
Small
Ski
Free Wi-Fi
Ski in-out, Slope and Pool Views 1BR at Country Inn main photo
Ski in-out, Slope and Pool Views 1BR at Country Inn
7.9 km from Pittsfield
Aparthotel in Hancock MAUS flag
0.0
$
+5
Info
Categories
Small
Pool
Outdoor Pool
Free Wi-Fi
Disney Magic at Jiminy Mountain main photo
Disney Magic at Jiminy Mountain
7.9 km from Pittsfield
Hotel in Hancock MAUS flag
7.9
Good
$
+11
Info
Categories
Small
Ski
Pool
Heated Pool
Outdoor Pool
Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury main photo
Gorgeous Ski On/Off 2 BR Sleeps 8 Jiminy-Must See Luxury
7.9 km from Pittsfield
Aparthotel in Hancock MAUS flag
8.1
Very Good
$
+7
Info
Categories
Small
Ski
Ski In Ski Out
Lakehouse Inn main photo
Lakehouse Inn
8.3 km from Pittsfield
Inn in Lee MAUS flag
9.3
Excellent
From $170
$
+1
Small
The Lakehouse Inn in Lee offers a tranquil lakeside setting, providing a relaxing and intimate escape. Its location and cozy atmosphere make it ideal for guests seeking a peaceful retreat in the Berkshires.
Chambery Inn main photo
Chambery Inn
9.5 km from Pittsfield
Bed & Breakfast in Lee MAUS flag
9.1
Excellent
From $318
$
+2
Small
Housed in a restored 1885 schoolhouse, the Chambery Inn offers unique suites with fireplaces and whirlpool baths, perfect for a cozy and romantic getaway. The attention to detail in the restoration and the luxurious amenities make it stand out.
The Red Door B&B main photo
The Red Door B&B
9.5 km from Pittsfield
Bed & Breakfast in Lee MAUS flag
0.0
From $288
$
+6
Info
Categories
Small
Ski
Dog Friendly
Shaker Mill Inn main photo
Shaker Mill Inn
9.8 km from Pittsfield
Bed & Breakfast in West Stockbridge MAUS flag
9.5
Excellent
From $163
$
+6
Info
Categories
Small
Boutique-Style
Ski
*Additional taxes or fees may apply. Please check the final price before completing your booking.Showing 1-20 out of 61 hotels in and around Pittsfield
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