Pittsfield B&B

Start date: Check-in selected.
To Date
End date: Check-out

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

B&B in Pittsfield

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
203 Main St Lenox MA
$177 nightly
The price is $198 total per night
$198 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Free Cancellation
Reserve now, pay when you stay
With a stay at The Cornell Inn, Lenox & The Berkshires in Lenox, you'll be in the historical district, within a 5-minute drive of Tanglewood Music Center and The Bookstore.
Shaker Mill Inn

Shaker Mill Inn

2.5 out of 5
2 Oak Street West Stockbridge MA
$112 nightly
The price is $123 total per night
$123 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
With a stay at Shaker Mill Inn in West Stockbridge, you'll be within a 15-minute drive of Tanglewood Music Center and Ebenezer II Gifts and Antiques.
Lakehouse Inn

Lakehouse Inn

4 out of 5
615 Laurel St. Lee MA
$193 nightly
The price is $216 total per night
$216 total
Jan 15 - Jan 16, 2026
Total with taxes and fees
With a stay at Lakehouse Inn in Lee, you'll be on a lake, within a 10-minute drive of Tanglewood Music Center and Berkshire Mountain Country Store.
Breakfast included
Parking included
Chambery Inn

Chambery Inn

3 out of 5
199 Main St Lee MA
$190 nightly
The price is $212 total per night
$212 total
Dec 28 - Dec 29
Total with taxes and fees
A stay at Chambery Inn places you in the heart of Lee, a 4-minute drive from Lee Premium Outlets and 6 minutes from The Mount.
Hot Tub
Spa
The Trail in Adams - Berkshires’ Art Hotel

The Trail in Adams - Berkshires’ Art Hotel

2.5 out of 5
10 Pleasant Street Adams MA
$174 nightly
The price is $194 total per night
$194 total
Dec 26 - Dec 27
Total with taxes and fees
Located in Adams, The Trail in Adams - Berkshires’ Art Hotel is in the mountains, just a 4-minute walk from Adams Theater and a 2-minute drive from Susan B. Anthony Birthplace Museum.
Granville House

Granville House

3 out of 5
98 Division St Housatonic MA
$224 nightly
The price is $250 total per night
$250 total
Dec 29 - Dec 30
Total with taxes and fees
Located in Housatonic, Granville House is within a 5-minute drive of Housatonic River and Monument Mountain.
Breakfast included
Pet friendly
Brook Farm Inn

Brook Farm Inn

3.5 out of 5
15 Hawthorne Street Lenox MA
$165 nightly
The price is $184 total per night
$184 total
Dec 30 - Dec 31
Total with taxes and fees
When you stay at Brook Farm Inn in Lenox, you'll be near ski lifts, within a 5-minute drive of Tanglewood Music Center and Shakespeare and Company.
Pool
Breakfast included
Inn at Silver Maple Farm

Inn at Silver Maple Farm

3 out of 5
1871 State Route 295 East Chatham NY
$129 nightly
The price is $144 total per night
$144 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Located in East Chatham, Inn at Silver Maple Farm is within a 15-minute drive of Furnace Brook Winery at Hilltop Orchards and Mount Lebanon Shaker Village.
Devonfield Inn B&B

Devonfield Inn B&B

4 out of 5
85 Stockbridge Rd. Lee MA
$369 nightly
The price is $412 total per night
$412 total
Jan 22 - Jan 23, 2026
Total with taxes and fees
With a stay at Devonfield Inn B&B in Lee, you'll be next to a golf course, within a 15-minute drive of Tanglewood Music Center and Greenock Country Club.
Whistler's Inn Bed & Breakfast

Whistler's Inn Bed & Breakfast

3.5 out of 5
5 Greenwood Street Lenox MA
When you stay at Whistler's Inn Bed & Breakfast in Lenox, you'll be in the historical district, within a 5-minute drive of Wyndhurst Golf & Club and Tanglewood Music Center.
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
26 Glendale Road, RR 183 Stockbridge MA
$414 nightly
The price is $462 total per night
$462 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
When you stay at The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood in Stockbridge, you'll be next to a golf course, within a 5-minute drive of Berkshire Botanical Garden and Norman Rockwell Museum.
33 Main

33 Main

4 out of 5
33 Main Street Lenox MA
$420 nightly
The price is $469 total per night
$469 total
Jan 25 - Jan 26, 2026
Total with taxes and fees
With a stay at 33 Main, you'll be centrally located in Lenox, within a 5-minute drive of Tanglewood Music Center and The Bookstore.
Don't see what you're looking for?
See all available properties in Pittsfield
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Pittsfield B&B essential information

Accommodation
35 B&B
Lowest Price
$123
Highest Price
$469
Popular accommodation
The Cornell Inn, Lenox & The Berkshires, Shaker Mill Inn, Lakehouse Inn, Chambery Inn, The Trail in Adams - Berkshires’ Art Hotel, Granville House, Brook Farm Inn, Inn at Silver Maple Farm, Devonfield Inn B&B, Whistler's Inn Bed & Breakfast, The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood, 33 Main

Explore more B&B

Types of Hotels

Top 20 Pittsfield Hotels

Hotels Near Pittsfield

Top Hotel Brands

Hotels By Star Rating

Cities near Pittsfield