Find Historic Hotels in The Berkshires, MA

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Check availability on The Berkshires Historic Hotels

Our top choices for The Berkshires historic hotels

Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,006 reviews)
"a delightful inn centrally located in charming Stockbridge"
United States
molly
The price is AED 559
AED 788 total
includes taxes & fees
22 Jun - 23 Jun
The Red Lion Inn
Exterior

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
10.0 out of 10, Exceptional, (107 reviews)
"Cozy spot with lots of thoughtful details. "
United States
Michelle Y.
The price is AED 551
AED 972 total
includes taxes & fees
5 Jul - 6 Jul
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Fridge, microwave, oven, stovetop

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Hoosick Falls
9.8 out of 10, Exceptional, (105 reviews)
"The host was very responsive and helpful. The property itself was also fantastic, with plenty of amenities and kept very clean."
United States
Jon
The price is AED 426
AED 1,146 total
includes taxes & fees
22 Jun - 23 Jun
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Outdoor dining

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Collinsville
10.0 out of 10, Exceptional, (65 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is AED 1,031
AED 1,726 total
includes taxes & fees
15 Jun - 16 Jun
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Interior

rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is AED 1,055
AED 1,321 total
includes taxes & fees
15 Jun - 16 Jun
rural, serene + sophisticated space
Fridge, microwave, oven, stovetop

A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (13 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is AED 3,269
AED 5,410 total
includes taxes & fees
15 Jun - 16 Jun
A Country Lodge Straight Out of the Pages of a Great Novel
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.
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Top The Berkshires Hotel Reviews

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Very clean. Accessible room was spacious. However, very little turning radius in bathroom, toilet not elevated and can’t fit under vanity."
Bernard 2-night trip
Posted 2 hours ago
Hotel Downstreet, an Ascend Collection Hotel

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