Historic Hotels & Resorts in The Berkshires from NZ$394

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Historic Hotels

Best 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, (1004)
"Food was great!"
The price is NZ$432
includes taxes & fees
27 Aug - 28 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 NZ$453
includes taxes & fees
24 Aug - 25 Aug
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
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 NZ$754
includes taxes & fees
19 Aug - 20 Aug
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 NZ$394
includes taxes & fees
19 Aug - 20 Aug
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
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)
"We had another wonderful stay despite the weather, thank you for letting us enjoy your beautiful home"
The price is NZ$659
includes taxes & fees
27 Aug - 28 Aug
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
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, (21)
"This was a wonderful trip! Absolutely loved the space and location. Loved the walking trail nearby and the little town. Will definitely be back :) "
The price is NZ$518
includes taxes & fees
31 Aug - 1 Sept
River Overlook - Check the view from your deck!
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 NZ$767
includes taxes & fees
19 Aug - 20 Aug
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
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."
Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
rural, serene + sophisticated space
Interior

rural, serene + sophisticated space

10.0 out of 10, Exceptional, (7)
"Beautiful property with unique accommodations in the Hudson Valley"
The price is NZ$741
includes taxes & fees
17 Sept - 18 Sept
rural, serene + sophisticated space
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Great place to stay"
RICHARD 1-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham