Find Historic Hotels in The Berkshires, MA
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on The Berkshires Historic Hotels
Tonight
29 Aug - 30 AugTomorrow
30 Aug - 31 AugNext weekend
4 Sep - 6 SepIn two weeks
11 Sep - 13 SepOur top choices for The Berkshires historic hotels
AED 550
AED 796 total
includes taxes & fees
29 Sep - 30 Sep
2. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country InnHancock
Kristina L.
AED 383
AED 863 total
includes taxes & fees
31 Aug - 1 Sep
3. A roomy remodeled retreat close to MassMoCA
A roomy remodeled retreat close to MassMoCANorth Adams
Jennifer O.
AED 841
AED 1,781 total
includes taxes & fees
9 Sep - 10 Sep
4. A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!Granby
Kristen S.
AED 496
AED 927 total
includes taxes & fees
8 Sep - 9 Sep
5. 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
Mike
AED 1,146
AED 1,953 total
includes taxes & fees
10 Sep - 11 Sep
6. 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
Anita T.
AED 691
AED 1,460 total
includes taxes & fees
8 Sep - 9 Sep
AED 1,055
AED 1,350 total
includes taxes & fees
31 Aug - 1 Sep
8. A Country Lodge Straight Out of the Pages of a Great Novel
A Country Lodge Straight Out of the Pages of a Great NovelPine Plains
Hessie S.
AED 3,269
AED 5,410 total
includes taxes & fees
31 Aug - 1 Sep
Top The Berkshires Hotel Reviews
Hotel On North
10/10 Excellent
"One of my favorite hotels in America - for real!"
The Red Lion Inn
10/10 Excellent
"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"
The Cornell Inn, Lenox & The Berkshires
10/10 Excellent
"Room was"
The Yankee Inn
10/10 Excellent
"One of the quietest rooms we have ever stayed in. The location was very convenient to sites in both Lenox and Stockbridge."
The Little Lion
8/10 Good
"Clean and comfortable room for reasonable price. Central area/lobby is nice place to sit and read, relax, and/or eat breakfast (coffee provided). Also red Adirondack chairs up on hill behind rooms and small tables/chairs in front of some rooms. Can use the outdoor pool and whirl pool a few miles away at the Red Lion Inn, which is desirable feature on summer days. A few negatives. While the building and rooms are set back from the road, it’s located off a busy road that goes between Stockbridge and Great Barrington. You will hear the cars during the day. It’s also not what I would consider an “Inn” as it’s really a motel. It used to be the Briarcliff Motel before the Red Lion Inn purchased it. Any questions, requests, or comments need to contact them as the Little Lion didn’t have any full time staff and no one at front desk in the lobby when we stayed. We received text with code for room door."
Hotel Downstreet, an Ascend Collection Hotel
10/10 Excellent
"Nice place"
Best Western Plus Berkshire Hills Inn & Suites
10/10 Excellent
"Fine place to stay in the Lenox area."
Explore a world of travel with Expedia
- Accor Hotels in Blandford
- Hotels with an Indoor Pool in The Berkshires
- Cabin Rentals in Sheffield
- Beach Hotels in Stockbridge
- Condo Rentals in Mill River
- 5 Star Hotels in Mill River
- America's Best Inns Hotels in Chester
- Casino Hotels in The Berkshires
- B&B in Great Barrington
- Vacation Homes in New Marlborough
- Hotels with Hot Tubs in Stockbridge
- Historic Hotels in Becket
- 5 Star Hotels in Otis
- Hotels with Hot Tubs in The Berkshires
- Hotels with a Pool in Sheffield
- Aparthotels in The Berkshires
- Cabin Rentals in The Berkshires
- Resorts in The Berkshires
- Golf Hotels in Great Barrington
- Cabin Rentals in South Lee
- Condo Resorts in New Marlborough
- Hotel Wedding Venues Hotels in Stockbridge
- Business Hotels in New Marlborough
- Hotel with a Concierge Hotels in Great Barrington
- Independent Hotels in New Marlborough
- Condo Resorts in The Berkshires
- Marriott Hotels & Resorts in Chester
- Motel 6 Hotels in Blandford
- Winery Hotels in The Berkshires
- B&B in The Berkshires
- Resorts & Hotels with Spas in Great Barrington
- Pet-Friendly Hotels in New Marlborough
- Cottages in Chester
- Hotels with WiFi in Great Barrington
- 4 Star Hotels in Sheffield
- Monterey Hotels
- Romantic Hotels in Becket
- Hotels with Bars in The Berkshires
- Inns in Blandford
- Hotels near National Shrine of the Divine Mercy
- 2 Star Hotels in Sheffield
- Cottages in The Berkshires
- Hotels near Ski Butternut
- B&B in Tyringham
- 5 Star Hotels in The Berkshires
- Farmstay in The Berkshires
- 3 Star Hotels in Sheffield
- Historic Hotels in Sheffield
- Independent Hotels in Blandford
- Cottages in Sheffield
- 2 Star Hotels in Beartown State Forest
- Guest Houses in South Lee
- Cheap Hotels in Lee
- Adults Only Resorts & in Lenox
- 4 Star Hotels in The Berkshires
- Cottages in Beartown State Forest
- Wyndham Hotels in Blandford
- Hotels with a Pool in New Marlborough
- Historic Hotels in South Lee
- Casino Hotels in Great Barrington
- 5 Star Hotels in Tyringham
- 2 Star Hotels in Sandisfield
- Lodges in Chester
- Boutique Hotels in Lenox
- 5 Star Hotels in Sheffield
- Cabin Rentals in Lee
- Motels in Great Barrington
- Vacation Homes in Mill River
- Romantic Hotels in Lee
- Hotels with Bars in Great Barrington
- Motels in Becket
- Villas in South Lee
- Daiwa Royal Hotels in Lee
- Family Hotels in Lenox
- 5 Star Hotels in Monterey
- Condo Rentals in Lee
- Cabin Rentals in Monterey
- Hotel Wedding Venues Hotels in Great Barrington
- Resorts in Becket
- 3 Star Hotels in Blandford
- Pet-Friendly Hotels in The Berkshires
- Red Carpet Inn Hotels in Blandford
- B&B in South Lee
- Villas in Tyringham
- Great Barrington Hotels
- Wyndham Hotels in Tyringham
- 3 Star Hotels in Monterey
- Inns in The Berkshires
- Hotels with Free Parking in Becket
- Cabin Rentals in Otis
- Lodges in The Berkshires
- Cabin Rentals in Blandford