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
8 Sep - 9 SepTomorrow
9 Sep - 10 SepThis weekend
11 Sep - 13 SepNext weekend
18 Sep - 20 SepOur top choices for The Berkshires historic hotels
AED 577
AED 826 total
includes taxes & fees
28 Sep - 29 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.
3. A roomy remodeled retreat close to MassMoCA
A roomy remodeled retreat close to MassMoCANorth Adams
Jennifer O.
AED 841
AED 1,768 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 923 total
includes taxes & fees
9 Sep - 10 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 1,031
AED 1,795 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 1,440 total
includes taxes & fees
10 Sep - 11 Sep
7. 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
13 Sep - 14 Sep
Top The Berkshires Hotel Reviews
The Red Lion Inn
8/10 Good
"The Inn is very welcoming with a broad front porch filled with wicker chairs and rockers. Inside there are many sitting rooms, a restaurant and tavern, gift and floral shops and access to an outdoor pool. Well loved antiques are everywhere for comfortable seating throughout the property. Rooms facing the streets can be noisy with traffic. Lots of atmosphere, history and great location for shopping, sightseeing and dining."
Hotel On North
10/10 Excellent
"Best place in town"
Willows Motel Williamstown
10/10 Excellent
"Great location. Outside of hotel is a little dated but the room Amazing breakfast. The owners really take pride in providing fresh healthy options."
The Yankee Inn
10/10 Excellent
"On an overpriced holiday weekend in the Berkshires, Yankee Inn was a great balance of price and amenities. The indoor pool was nicer than most, and the hot tub was great. Outdoor pool was a bit oddly placed between the parking lot and the main road, but nice as well. Both very clean. Room was spacious and clean, beds were comfortable, though I think they were doubles rather than queens. The included breakfast was on the very good end of standard - the fruit was fresh and delicious, there were both eggs and waffles, plus cereal, yogurt, bacon/sausage. Meh on the pastries, and the coffee was terribly watery. My true only gripe is that there was truly not a single place to hang wet bathing suits that didn't result in them dripping all over the floor. Had we been on the 2nd floor, we would have had an outside railing, but on the first floor there was none. With 4 people using the pool and hot tub, it was an annoyance. Overall, great place for a quick stay."
Hotel Downstreet, an Ascend Collection Hotel
8/10 Good
"Nice and conveniently located"
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