Find Winery Hotels in The Berkshires, MA

Start date: Check-in selected.
To Date
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 The Berkshires Winery Hotels

Tonight
Sep 25 - Sep 26
Tomorrow
Sep 26 - Sep 27
This weekend
Sep 26 - Sep 28
Next weekend
Oct 3 - Oct 5

Top The Berkshires Winery Hotels

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, (1012)
"The staff and location make it excellent"
The price is ￥18,848
￥21,053 total
includes taxes & fees
Oct 1 - Oct 2
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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, (65)
"Very nice stay "
The price is ￥28,127
￥31,784 total
includes taxes & fees
Sep 29 - Sep 30
Wm. Farmer & Sons
Nautical Nest
Premium bedding, memory foam beds, individually decorated

Nautical Nest

2.5 star property
9.6 out of 10, Exceptional, (120)
"Loved the location and the decor. Little details such as the shared kitchen were great, too. Instructions from operator were timely and prompt. Would definitely stay again. Thanks!"
The price is ￥18,913
￥21,940 total
includes taxes & fees
Sep 29 - Sep 30
Nautical Nest
East Rock Inn
Premium Apartment | Private kitchen | Electric kettle

East Rock Inn

2.0 star property
9.4 out of 10, Exceptional, (32)
"Room was really comfortable and clean. Beautiful views from the main court yard during the day and at night the sky was full of stars. Amazing. "
The price is ￥21,493
￥24,008 total
includes taxes & fees
Oct 1 - Oct 2
East Rock Inn
Berkshire Valley Inn
Exterior

Berkshire Valley Inn

2.5 star property
9.2 out of 10, Wonderful, (561)
"Beautiful property, wonderful staff, great breakfast. "
The price is ￥24,577
￥27,452 total
includes taxes & fees
Oct 1 - Oct 2
Berkshire Valley Inn
The Amelia
Seasonal outdoor pool, pool umbrellas, sun loungers

The Amelia

2.0 star property
10.0 out of 10, Exceptional, (23)
"Beautiful hotel, great service. Loved the fresh baked goodies a s"
The Amelia
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
Gateways Inn & Restaurant
Room (King Room) | Iron/ironing board, free WiFi, bed sheets

Gateways Inn & Restaurant

3.0 star property
8.0 out of 10, Very Good, (190)
"Very well kept property, nice restaurant and is in a great area"
The price is ￥26,913
￥31,408 total
includes taxes & fees
Sep 28 - Sep 29
Gateways Inn & Restaurant
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 ￥24,109
￥59,012 total
includes taxes & fees
Sep 28 - Sep 29
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Charming apartment 7 minute walk to downtown
Fridge, microwave, oven, stovetop

Charming apartment 7 minute walk to downtown

10.0 out of 10, Exceptional, (15)
"Everything about our stay was great - Corin and Jen were wonderful hosts. The place is spotless, cozy, comfy. Love that they were right next to the Green Way Trail along the river. Will absolutely stay there again! "
The price is ￥19,823
￥36,041 total
includes taxes & fees
Sep 28 - Sep 29
Charming apartment 7 minute walk to downtown
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.
View all properties

Top The Berkshires Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"It's just a nice place and the staff is very nice "
Robin 5-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham

Explore a world of travel with Expedia

Explore a world of travel with Expedia