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

Small Hotels in Pittsfield

100 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
Berkshire Nook main photo
Berkshire Nook
Bed & Breakfast in Pittsfield MAUS flag
0.0
$
+3
Info
Categories
Small
Free Wi-Fi
Parking
18 more hotels nearby!
Wagon Wheel Inn main photo
Wagon Wheel Inn
3.0 mi from Pittsfield
Motel in Lenox MAUS flag
6.6
Rated
From $71
$
+1
Info
Categories
Small
Ski
Knights Inn Lenox main photo
Knights Inn Lenox
3.1 mi from Pittsfield
Motel in Lenox MAUS flag
6.1
Rated
From $166
$
+2
Info
Categories
Small
Ski
Weathervane Motel Lanesboro main photo
Weathervane Motel Lanesboro
4.0 mi from Pittsfield
Motel in Lanesborough MAUS flag
7.0
Good
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 mi 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 mi from Pittsfield
Bed & Breakfast in Lenox MAUS flag
8.1
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 mi from Pittsfield
Hotel in Lenox MAUS flag
0.0
$
+4
Info
Categories
Small
Free Wi-Fi
Parking
Inn at Richmond main photo
Inn at Richmond
6.2 mi from Pittsfield
Bed & Breakfast in Richmond MAUS flag
0.0
From $382
$
+3
Info
Categories
Small
Ski
Dog Friendly
The Inn at Richmond main photo
The Inn at Richmond
6.2 mi 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 mi from Pittsfield
Inn in Lenox MAUS flag
8.7
Very Good
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.
The Summer White House Inn main photo
The Summer White House Inn
6.4 mi from Pittsfield
Bed & Breakfast in Lenox MAUS flag
0.0
From $93
$
+4
Info
Categories
Small
Ski
Free Wi-Fi
Doctor Sax House main photo
Doctor Sax House
6.4 mi from Pittsfield
Hotel in Lenox MAUS flag
9.1
Excellent
$
+2
Info
Categories
Small
Dog Friendly
Parking
Gateways Inn main photo
Gateways Inn
6.4 mi from Pittsfield
Bed & Breakfast in Lenox MAUS flag
9.0
Excellent
From $241
$
+4
Info
Categories
Small
Parking
EV charging stations
Ski
Hampton Terrace Inn main photo
Hampton Terrace Inn
6.5 mi from Pittsfield
Hotel in Lenox MAUS flag
9.2
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.
Kemble Inn - Restaurant - Bar main photo
Kemble Inn - Restaurant - Bar
6.5 mi from Pittsfield
Hotel in Lenox MAUS flag
8.5
Very Good
From $49
$
+6
Info
Categories
Small
Golf
Ski
Brook Farm Inn main photo
Brook Farm Inn
6.8 mi from Pittsfield
Bed & Breakfast in Lenox MAUS flag
9.0
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.
Chesapeake Inn of Lenox main photo
Chesapeake Inn of Lenox
6.9 mi from Pittsfield
Inn in Lenox MAUS flag
8.0
Very Good
From $30
$
+12
Info
Categories
Small
Parking
EV charging stations
Ski
Eastgate Inn B&B main photo
Eastgate Inn B&B
6.9 mi 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 mi from Pittsfield
Bed & Breakfast in Lenox MAUS flag
9.8
Excellent
From $197
$
+4
Info
Categories
Small
Ski
Free Wi-Fi
*Additional taxes or fees may apply. Please check the final price before completing your booking.Showing 1-20 out of 100 hotels in and around Pittsfield
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Small Hotels, B&Bs, Motels, Inns in Pittsfield MA