Photo by Photo courtesy of Berkshire Visitors Bureau
Winery Hotels & Resorts in The Berkshires from AU$190
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on The Berkshires Winery Hotels
Our top choices for The Berkshires hotels with winery
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
9.0 out of 10, Wonderful, (1,000 reviews)
"Nice location. Can rent their pontoon boat."
Paul
The price is AU$190
includes taxes & fees
20 May - 21 May
9.4 out of 10, Exceptional, (164 reviews)
"Everything was perfect - location and accommodation."
Christopher
The price is AU$294
includes taxes & fees
2 June - 3 June
9.4 out of 10, Exceptional, (44 reviews)
"The East Rock Inn is great. It's comfortable, clean and close to downtown Great Barrington. This was my second time staying here."
Laura
The price is AU$212
includes taxes & fees
17 May - 18 May
9.2 out of 10, Wonderful, (567 reviews)
"Cozy, homey feel of our suite. You can tell the owner takes pride of her inn— cute Pinterest inspiration decoration in the room and lobby.
The free breakfast and coffee is a great start to the morning.
Close to Jiminy Peak, so easy to ski and come back before the kids fall asleep. "
Sue
The price is AU$193
includes taxes & fees
14 May - 15 May
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
The price is AU$514
includes taxes & fees
14 May - 15 May
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Cozy. Clean. Free bagel shop. 3 Fireplaces.Great Barrington
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
Mary R.
The price is AU$734
includes taxes & fees
14 May - 15 May
The price is AU$229
includes taxes & fees
19 May - 20 May
9.2 out of 10, Wonderful, (91 reviews)
"My stay was just lovely! Exactly what I was looking for. Everything smelled great, was beautiful to look it and the staff was sweet and accommodating! I’ll be back."
Stephane
The price is AU$263
includes taxes & fees
18 May - 19 May
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 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