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Featured Pittsfield Independent Hotels

See all 165 Hotels in Pittsfield
Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Hancock
3.0 out of 5.0
4.2 out of 5 (796 reviews)
Good location Close to ski. Kids enjoyed pool and arcade. Kitchens make it easy to plan meals if you are on a bud … - 

$135

$135
Yankee Inn

Yankee Inn

461 Pittsfield Rd, Lenox
3.0 out of 5.0
3.9 out of 5 (499 reviews)
Visited this past President's Day weekend. To begin, our check-in was quick and easy. We found our … - 

$80

$80
The Williams Inn

The Williams Inn

1090 Main Street, Williamstown
3.5 out of 5.0
3.9 out of 5 (163 reviews)
Quaint and quiet stay Very nice room and grounds of the hotel. Perfect for a nice getaway. Breakfast was delicious! - 

$125

$125
Cranwell Spa and Golf Resort

Cranwell Spa and Golf Resort

55 Lee Road, Lenox
3.5 out of 5.0
4.2 out of 5 (110 reviews)
Such a beautiful resort This was a mini getaway weekend for myself and daughters. The resort is gorgeous and relaxing!! I l … - 

$119

$119
Hotel On North

Hotel On North

297 North Street, Pittsfield
4.0 out of 5.0
4.8 out of 5 (137 reviews)
Central location - main street - across from the Y - 

$159

$159
Berkshire Hills Country Inn

Berkshire Hills Country Inn

1146 Cold Spring Road, Williamstown
2.5 out of 5.0
4.1 out of 5 (83 reviews)
Cozy country motel. Very clean and comfortable. Great staff. - 

$65

$65
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

37 Corey Rd, Hancock
3.5 out of 5.0
4.0 out of 5 (508 reviews)
Family friendly and courteous staff Staff is so friendly and helpful. Resort is so convenient for families with everything right on the … - 

$159

$159
Berkshire Mountain Lodge

Berkshire Mountain Lodge

8 Dan Fox Dr, Pittsfield
3.5 out of 5.0

$178

$178
Berkshire Inn

Berkshire Inn

150 W Housatonic St, Pittsfield
2.5 out of 5.0
3.5 out of 5 (148 reviews)
Nice motel all year round Very pleasant stay. Extreme cold winter condtions at time of stay. I flooded my car and the manager … - 

$59

$59
The Red Lion Inn

The Red Lion Inn

30 Main Street, Stockbridge
4.0 out of 5.0
4.3 out of 5 (169 reviews)
Character filled and charming We were expediently checked in and when a quick review of their menu showed little to offer for the … - 

$136

$136
The Porches Inn

The Porches Inn

231 River Street, North Adams
4.0 out of 5.0
4.6 out of 5 (103 reviews)
Great stay Great place, awesome location, walking distance to solid brewery. Only complaint is pillow too soft … - 

$149

$149
Monument Mountain Motel

Monument Mountain Motel

247 Stockbridge Rd, Great Barrington
3.0 out of 5.0
4.4 out of 5 (81 reviews)
Great value in an excellent locatoln This property was exactly what my family was looong for when we went skiing at butternut. The motel … - 

$60

$60
Chambery Inn

Chambery Inn

199 Main St, Lee
3.5 out of 5.0
4.7 out of 5 (144 reviews)
I have family in town and always stay at the Chambery when visiting. It's sooo much nicer than anyt … - 
Maplewood Bed & Breakfast

Maplewood Bed & Breakfast

435 Maple St., Hinsdale
4.0 out of 5.0
4.9 out of 5 (10 reviews)
a very nice B&B with a history longer than US This nice B&B is well-kept by Steve and Christy who are warm-hearted and hard-working persons. My w … - 

$100

$100
Kemble Inn

Kemble Inn

2 Kemble Street, Lenox
4.0 out of 5.0
4.4 out of 5 (10 reviews)
Anniversary 5 ⭐️- Wonderful place and excellent staff!! Andrea V DiMattia - 
The Villager Motel

The Villager Motel

953 Simonds Rd, Williamstown
2.5 out of 5.0
3.7 out of 5 (116 reviews)
The motel was cute and clean. A great place for the price. - 

$49

$49
Maple Terrace Motel

Maple Terrace Motel

555 Main St., Williamstown
2.5 out of 5.0
4.6 out of 5 (41 reviews)
Quiet and delightful, even on a very chilly weekend! The room was warm and cozy, the space just wha … - 

$64

$64
The Inn at Stockbridge

The Inn at Stockbridge

30 East Street, Stockbridge
4.5 out of 5.0
4.8 out of 5 (30 reviews)
Wonderful My wife and I stayed for 3 nights, and we had a great time. The accommodations were clean, quiet, a … - 

$130

$130
Lantern House Motel

Lantern House Motel

256 Stockbridge Road, Great Barrington
3.0 out of 5.0
4.0 out of 5 (145 reviews)
Very comfortable and pleasant stay! Our room was upgraded and was very comfortable . We willuminiun be staying here again! - 
Garden Gables Inn

Garden Gables Inn

135 Main St, Lenox
4.5 out of 5.0
5.0 out of 5 (3 reviews)
Nice Bed and Breakfast close to Tanglewood. My stay here was lovely. Martie, the Innkeeper, was hospitable and accommodating. The rooms were cl … - 
Map

Recently booked Pittsfield hotels

Berkshire Inn
2.5 out of 5.0
Last booking: 2 hours ago
Crowne Plaza Pittsfield-Berkshires
4.0 out of 5.0
Last booking: 2 hours ago
Best Western Plus Berkshire Hills Inn & Suites
3.0 out of 5.0
Last booking: 6 hours ago
Hotel On North
4.0 out of 5.0
Last booking: 17 hours ago
Econo Lodge
2.0 out of 5.0
Last booking: 30 hours ago
Hilton Garden Inn Lenox/Pittsfield
3.5 out of 5.0
Last booking: 41 hours ago

Independent Pittsfield Hotel Guide

Some globe-trotters choose hotels based on location, but others book by name. And thanks to Expedia you don’t have to pick. It is why we offer such an expansive range of Independent hotels in Pittsfield, Massachusetts. Known for well-appointed rooms and friendly, personalized service, each of the top Independent Pittsfield hotels guarantees an unparalleled level of comfort and quality.

You’ll find best-in-class amenities like clean rooms and quiet atmospheres, and some Pittsfield Independent locations may even offer extra little benefits and discounts for frequent travelers.