The Berkshires Hotel Guide - Historic Hotels in The Berkshires, Massachusetts

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Top The Berkshires Historic Hotels

The Red Lion Inn
Outdoor pool, pool loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1003)
"Loved our visit"
The price is €226
includes taxes & fees
19 Aug - 20 Aug
The Red Lion Inn
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Exterior detail

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

10.0 out of 10, Exceptional, (88)
"Enjoyed staying"
The price is €235
includes taxes & fees
17 Aug - 18 Aug
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Exterior

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

10.0 out of 10, Exceptional, (23)
"This property is spacious, clean and well- appointed. I would stay here again!"
The price is €207
includes taxes & fees
18 Aug - 19 Aug
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
North Getaway Cottage
Exterior

North Getaway Cottage

9.6 out of 10, Exceptional, (20)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is €390
includes taxes & fees
18 Aug - 19 Aug
North Getaway Cottage
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Exterior detail

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

9.8 out of 10, Exceptional, (93)
"This VRBO was stocked to the brim with everything you would need. It was on the boarder of three different states , nestled on five acres of private property. It was the perfect private weekend getaway . Highly recommend for any family looking for a ski trip. The host responded to anything we needed immediately. We will definitely be back, 5 out of 5."
The price is €343
includes taxes & fees
27 Aug - 28 Aug
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (58)
"We were visiting University of Hartford and this was the perfect place to stay outside of the city. Great space with all the conveniences of home. Wonderful food options within walking distance. "
The price is €397
includes taxes & fees
18 Aug - 19 Aug
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
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.

Top The Berkshires Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"..."
adriana 1-night trip
Posted 2 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG