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Check availability on The Berkshires Romantic Hotels

Our top choices for The Berkshires romantic hotels

Terrace/patio

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (277 reviews)
"The property is very nice, well stocked amenities. Cozy and warm and perfect for a long weekend getaway. "
United States
Jonathan H.
The price is AED 496
AED 771 total
includes taxes & fees
22 May - 23 May
Berkshire Village Carriage House - Super Private!!
Indoor pool

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
The price is AED 397
AED 878 total
includes taxes & fees
19 May - 20 May
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Outdoor pool, a heated pool

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is AED 225
AED 1,151 total
includes taxes & fees
17 May - 18 May
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Fridge, microwave, oven, stovetop

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
9.8 out of 10, Exceptional, (105 reviews)
"The host was very responsive and helpful. The property itself was also fantastic, with plenty of amenities and kept very clean."
United States
Jon
The price is AED 426
AED 1,134 total
includes taxes & fees
17 May - 18 May
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
Fireplace, books

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
10.0 out of 10, Exceptional, (105 reviews)
"Everything was lovely! The host was welcoming, the cottage was adorable. Amenities were great (fire was on when we got there, warming blankets on the bed). So cozy! Perfect place to snuggle up during the coldest weekend of the year. We'd definitely stay again. "
United States
Jennifer H.
The price is AED 463
AED 881 total
includes taxes & fees
19 May - 20 May
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Outdoor dining

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 Collinsville
Collinsville
10.0 out of 10, Exceptional, (65 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is AED 1,146
AED 1,931 total
includes taxes & fees
28 May - 29 May
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Exterior

Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK

Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK
Hillsdale
10.0 out of 10, Exceptional, (128 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is AED 793
AED 1,469 total
includes taxes & fees
17 May - 18 May
Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK
Smart TV, fireplace, video games, DVD player

Summer Escape Near Lakes, Trails & Mt Snow

Summer Escape Near Lakes, Trails & Mt Snow
Dover
10.0 out of 10, Exceptional, (44 reviews)
"Lovely house - perfect for a ski trip!"
United States
Alexander H.
The price is AED 856
AED 1,980 total
includes taxes & fees
19 May - 20 May
Summer Escape Near Lakes, Trails & Mt Snow
Interior

rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is AED 988
AED 1,251 total
includes taxes & fees
18 May - 19 May
rural, serene + sophisticated space
Outdoor pool, a heated pool

Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson

Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
Hudson
9.8 out of 10, Exceptional, (31 reviews)
"This house is a true treasure! It’s stunningly beautiful and cozy. We loved all the amenities and thoughtful touches, and walking into town was convenient. Absolutely recommend!"
United States
Leah A.
The price is AED 3,122
AED 5,209 total
includes taxes & fees
11 Jun - 12 Jun
Luxury Spa Retreat with Sauna, Hot Tub & Swimming Pool in the Heart of Hudson
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.
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Top The Berkshires Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Lovely and historic property. Friendly staff and very comfortable room. Dinner and breakfast were wonderful. We are repeat visitors. "
Anne 1-night trip
Posted 5 days ago
The Red Lion Inn

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