Photo by Photo courtesy of Berkshire Visitors Bureau
Historic Hotels & Resorts in The Berkshires from AU$304
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on The Berkshires Historic Hotels
Our top choices for The Berkshires historic hotels
8.8 out of 10, Excellent, (1002)
"Old time charm and hot tub under the stars"
Lori
The price is AU$304
includes taxes & fees
14 Jan - 15 Jan 2026
10.0 out of 10, Exceptional, (27)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
Margaret
The price is AU$694
includes taxes & fees
5 Jan - 6 Jan 2026
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, (95)
"This was an incredibly beautiful place to spend a restful weekend. "
Meagan M.
The price is AU$404
includes taxes & fees
1 Jan - 2 Jan 2026
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, (100)
"Beautiful, serene location with great penned in area for my lovable, niece pup! Spacious house with all the key amenities. Easy access for my elederly mom. "
Lynn F.
The price is AU$463
includes taxes & fees
4 Jan - 5 Jan 2026
River Overlook - Check the view from your deck!
River Overlook - Check the view from your deck!Collinsville
10.0 out of 10, Exceptional, (23)
"The place was perfect for the two of us. It was close to both our kids homes."
Tomas M.
The price is AU$487
includes taxes & fees
19 Jan - 20 Jan 2026
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 CollinsvilleCollinsville
10.0 out of 10, Exceptional, (61)
"Fabulous location. I can honestly say cleanest VRBO we’ve ever stayed!!"
Jeanmarie G.
The price is AU$740
includes taxes & fees
30 Dec - 31 Dec
Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of HudsonHudson
9.8 out of 10, Exceptional, (27)
"Met our son and his girls for a little getaway. Very cool house complete with lots to do! Thank you. Hope to get to experience it during the summer months sometime."
Kathy M.
The price is AU$1,652
includes taxes & fees
13 Jan - 14 Jan 2026
rural, serene + sophisticated space
rural, serene + sophisticated spaceRed Hook
10.0 out of 10, Exceptional, (7)
"Beautiful property with unique accommodations in the Hudson Valley"
BRIAN PATRICK M.
The price is AU$575
includes taxes & fees
4 Jan - 5 Jan 2026
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 Red Lion Inn
10/10 Excellent
Explore a world of travel with Expedia
- B&B in Alford
- Cheap Hotels in Alford
- Alford Hotels
- Villas in Alford
- Beach Hotels in Becket
- Cheap Hotels in Becket
- Hotels with Parking in Becket
- Cheap Hotels in Blandford
- Luxury Hotels in Blandford
- Ski Hotels in Blandford
- Blandford Hotels
- B&B in Chester
- Chester Hotels
- Guest Houses in Granville
- Holiday Homes in Granville
- Cheap Hotels in Granville
- Granville Hotels
- Motels in Granville
- Great Barrington Hotels
- Motels in Great Barrington
- Cheap Hotels in Hinsdale
- Huntington Hotels
- Castles in Lee
- Lgbt Welcoming Hotels in Lee
- Lee Hotels
- Cottages in Lenox
- Boutique Hotels in Lenox
- Cheap Hotels in Lenox
- Lenox Hotels
- Inns in Lenox
- Caravan Parks in Mill River
- B&B in Monterey
- Condominium Resort in Monterey
- Cheap Hotels in Monterey
- Family Hotels in Monterey
- Monterey Hotels
- Resort in Monterey
- Hotels near National Shrine of the Divine Mercy
- Caravan Parks in New Marlborough
- Farmstay in New Marlborough
- Beach Hotels in New Marlborough
- Luxury Hotels in New Marlborough
- Spa Hotels in New Marlborough
- Winery Hotels in New Marlborough
- New Marlborough Hotels
- Lodges in New Marlborough
- Motels in New Marlborough
- Apartments in Otis
- Caravan Parks in Otis
- Holiday Homes in Otis
- Otis Hotels
- Lodges in Otis
- Hotels near Otis Ridge
- Cheap Hotels in Peru
- Cheap Hotels in Pittsfield
- Boutique Hotels in Richmond
- Hotels with Parking in Richmond
- Pet Friendly Hotels in Richmond
- Family Hotels in Russell
- Russell Hotels
- B&B in Sheffield
- Caravan Parks in Sheffield
- Historic Hotels in Sheffield
- Spa Hotels in Sheffield
- Sheffield Hotels
- Motels in Sheffield
- Sherwood Forest Hotels
- Hotels with Parking in South Egremont
- South Egremont Hotels
- Southfield Hotels
- Historic Hotels in Stockbridge
- Stockbridge Hotels
- Hotels near The Mount
- Luxury Hotels in Tolland
- Tolland Hotels
- Tyringham Hotels
- Lodges in Tyringham
- B&B in Washington
- Washington Hotels
- Luxury Hotels in Worthington