Historic Hotels & Resorts in The Berkshires

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

Tonight
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
3 Oct - 5 Oct
Next weekend
10 Oct - 12 Oct

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, (1001)
"great place have stayed several times, and hope to return."
The price is NZ$380
includes taxes & fees
2 Nov - 3 Nov
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, (90)
"Just stayed one night for our wedding. Beautiful and very quiet. Easy check in/check out process."
The price is NZ$455
includes taxes & fees
22 Oct - 23 Oct
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
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 NZ$893
includes taxes & fees
2 Nov - 3 Nov
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!"
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 NZ$516
includes taxes & fees
26 Oct - 27 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)
"We had another wonderful stay despite the weather, thank you for letting us enjoy your beautiful home"
The price is NZ$691
includes taxes & fees
6 Oct - 7 Oct
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
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 NZ$1,860
includes taxes & fees
29 Oct - 30 Oct
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 NZ$843
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
"Great place! Food excellent ss well!"
Crystal 1-night trip
Posted 2 days ago
The Red Lion Inn

Explore a world of travel with Expedia

Explore a world of travel with Expedia