Cheshire B&B
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B&B in Cheshire
The Cornell Inn, Lenox & The Berkshires
203 Main St Lenox MA
$172 nightly
The price is $192 total per night
$192 total
Dec 10 - Dec 11
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.
Breakfast included
Parking included
Shaker Mill Inn
2 Oak Street West Stockbridge MA
$109 nightly
The price is $120 total per night
$120 total
Dec 7 - Dec 8
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.
Breakfast included
Parking included
Lakehouse Inn
615 Laurel St. Lee MA
$195 nightly
The price is $218 total per night
$218 total
Dec 12 - Dec 13
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
199 Main St Lee MA
$190 nightly
The price is $212 total per night
$212 total
Dec 7 - Dec 8
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
10 Pleasant Street Adams MA
$174 nightly
The price is $194 total per night
$194 total
Dec 6 - Dec 7
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.
Parking included
Free WiFi
Brook Farm Inn
15 Hawthorne Street Lenox MA
$179 nightly
The price is $200 total per night
$200 total
Dec 11 - Dec 12
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
1871 State Route 295 East Chatham NY
$129 nightly
The price is $144 total per night
$144 total
Dec 8 - Dec 9
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.
Breakfast included
Parking included
Devonfield Inn B&B
85 Stockbridge Rd. Lee MA
$349 nightly
The price is $390 total per night
$390 total
Dec 8 - Dec 9
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.
Pool
Breakfast included
Whistler's Inn Bed & Breakfast
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.
Breakfast included
Pet friendly
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
26 Glendale Road, RR 183 Stockbridge MA
$414 nightly
The price is $462 total per night
$462 total
Dec 18 - Dec 19
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.
Pool
Breakfast included
33 Main
33 Main Street Lenox MA
$469 nightly
The price is $524 total per night
$524 total
Jan 5 - Jan 6, 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.
Breakfast included
Parking included
Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen
Lenox MA
$310 nightly
The price is $354 total per night
$354 total
Dec 7 - Dec 8
Total with taxes and fees
With a stay at this bed & breakfast in Lenox, you'll be within a 5-minute drive of Tanglewood Music Center and The Bookstore.
Air conditioning
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.
Cheshire B&B essential information
Accommodation | 35 B&B |
|---|---|
Lowest Price | $120 |
Highest Price | $524 |
Popular accommodation | The Cornell Inn, Lenox & The Berkshires, Shaker Mill Inn, Lakehouse Inn, Chambery Inn, The Trail in Adams - Berkshires’ Art Hotel, 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, Historic Cornell Inn - Cozy Berkshires Retreat - Lenox, MA - Basic Queen |