Find Winery Hotels in The Berkshires, MA from CA $136

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Check availability on The Berkshires Winery Hotels

Top The Berkshires Winery Hotels

Our top choices for The Berkshires hotels with winery

The Black Swan Lee - Lenox, Ascend Hotel Collection
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1001)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is CA $176
CA $196 total
includes taxes & fees
Sep 1 - Sep 2
The Black Swan Lee - Lenox, Ascend Hotel Collection
Nautical Nest
1 bedroom, premium bedding, memory foam beds, individually decorated

Nautical Nest

2.5 star property
9.6 out of 10, Exceptional, (116)
"Perfect location. "
The price is CA $174
CA $202 total
includes taxes & fees
Aug 25 - Aug 26
Nautical Nest
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 price is CA $556
CA $629 total
includes taxes & fees
Aug 25 - Aug 26
The Amelia
Gateways Inn & Restaurant
Room (King Room)

Gateways Inn & Restaurant

3.0 star property
7.8 out of 10, Good, (189)
"Very well kept property, nice restaurant and is in a great area"
The price is CA $390
CA $456 total
includes taxes & fees
Sep 16 - Sep 17
Gateways Inn & Restaurant
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 price is CA $229
CA $353 total
includes taxes & fees
Aug 25 - Aug 26
the suite @ barn & bike - private, bucolic, serene setting
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 CA $225
CA $555 total
includes taxes & fees
Sep 3 - Sep 4
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
All comforts of home
Property grounds

All comforts of home

9.8 out of 10, Exceptional, (47)
"Very clean, well-appointed, quiet location. Relaxing and pleasant."
The price is CA $136
CA $183 total
includes taxes & fees
Aug 27 - Aug 28
All comforts of home
The Creation Station is a cozy place so make yourself at home.
Property grounds

The Creation Station is a cozy place so make yourself at home.

10.0 out of 10, Exceptional, (67)
"This was our second time staying here and we had a great time!"
The price is CA $250
CA $384 total
includes taxes & fees
Aug 26 - Aug 27
The Creation Station is a cozy place so make yourself at home.
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)
"This place is beautiful and so clean. They thought of everything. Decorated beautifully. I would highly recommend staying here. "
The price is CA $205
CA $369 total
includes taxes & fees
Sep 8 - Sep 9
Charming apartment 7 minute walk to downtown
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Fridge, microwave, oven, stovetop

Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

10.0 out of 10, Exceptional, (12)
"Great property, plenty of space and room for all. Location is ideal"
The price is CA $323
CA $757 total
includes taxes & fees
Sep 15 - Sep 16
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
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, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"I love the cleanliness, courteous staff. Warm pool, hot tub. Relaxing environment."
Jeanette 2-night trip
Posted 3 days ago
The Yankee, Trademark Collection by Wyndham