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

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

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Historic Hotels

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, (1007)
"great place have stayed several times, and hope to return."
The price is €182
includes taxes & fees
6 Nov - 7 Nov
The Red Lion Inn
North Getaway Cottage
Exterior

North Getaway Cottage

9.2 out of 10, Wonderful, (22)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is €421
includes taxes & fees
27 Oct - 28 Oct
North Getaway Cottage
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 €217
includes taxes & fees
15 Oct - 16 Oct
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
River Overlook - Check the view from your deck!
Fridge, microwave, oven, stovetop

River Overlook - Check the view from your deck!

10.0 out of 10, Exceptional, (23)
"I only did a short stay (2 nights) but it was super adorable! I will definitely stay again when I'm back in the area."
The price is €265
includes taxes & fees
19 Oct - 20 Oct
River Overlook - Check the view from your deck!
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, (94)
"Quiet and relaxing property "
The price is €351
includes taxes & fees
22 Oct - 23 Oct
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
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, (90)
"Nice Area. Stone cottage rocks!"
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
Outdoor pool, a heated pool

Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson

9.6 out of 10, Exceptional, (25)
"We loved our stay and this house made our trip. The bathroom and kitchen were especially memorable but we loved all the little details that added up to one stunningly restored historic home."
The price is €978
includes taxes & fees
3 Nov - 4 Nov
Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
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, (61)
"There is a lot of fun things to do close by. The house was spotless and it was nice to relax on the sofa or outside patio and look at the river. "
The price is €392
includes taxes & fees
13 Oct - 14 Oct
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.
View all properties

Top The Berkshires Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Lovely historic hotel that we enjoyed but also knew going in not to expect modern…yes the floors creak and doors and windows dont fit snuggly. We loved it for all those reasns! Staff is wonderful! Enjoy the front porch while you are there!"
Connie 1-night trip
Posted 5 days ago
The Red Lion Inn

Explore a world of travel with Expedia

Explore a world of travel with Expedia