Find Winery Hotels in Great Barrington, MA

Start date: Check-in selected.
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 Great Barrington Winery Hotels

Top Great Barrington Winery Hotels

Our top choices for Great Barrington hotels with winery

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1005)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is SAR 475
SAR 531 total
includes taxes & fees
17 Sep - 18 Sep
The Black Swan Lee - Lenox, an Ascend Collection Hotel
East Rock Inn
Premium Apartment | Private kitchen | Electric kettle

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (30)
"Quit eat and comfortable "
The price is SAR 481
SAR 538 total
includes taxes & fees
23 Sep - 24 Sep
East Rock Inn
Wm. Farmer & Sons
Room, 1 King Bed, Balcony, Garden View | Balcony view

Wm. Farmer & Sons

2.5 star property
9.2 out of 10, Wonderful, (62)
"Very nice stay "
The price is SAR 709
SAR 801 total
includes taxes & fees
18 Sep - 19 Sep
Wm. Farmer & Sons
Nautical Nest
Premium bedding, memory foam beds, individually decorated

Nautical Nest

2.5 star property
9.6 out of 10, Exceptional, (118)
"Great location. Room needs a comfy chair"
The price is SAR 488
SAR 566 total
includes taxes & fees
11 Sep - 12 Sep
Nautical Nest
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Microwave, oven, stovetop, dishwasher

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (160)
"Inn was gorgeous and staff exceptional!"
Brook Farm Inn
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Outdoor dining

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
The price is SAR 608
SAR 1,488 total
includes taxes & fees
24 Sep - 25 Sep
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
the suite @ barn & bike - private, bucolic, serene setting
Interior

the suite @ barn & bike - private, bucolic, serene setting

9.8 out of 10, Exceptional, (14)
"We enjoyed our stay at this quiet, cozy property."
the suite @ barn & bike - private, bucolic, serene setting
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)
"Enjoyed staying"
The price is SAR 563
SAR 992 total
includes taxes & fees
17 Sep - 18 Sep
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
All the comforts of home
Property grounds

All the comforts of home

9.2 out of 10, Wonderful, (25)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
The price is SAR 398
SAR 530 total
includes taxes & fees
10 Sep - 11 Sep
All the comforts of home
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 Great Barrington Hotel Reviews

Explore a world of travel with Expedia

Explore a world of travel with Expedia