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The Berkshires Hotel Guide - Romantic Hotels in The Berkshires, Massachusetts
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Our top choices for The Berkshires romantic hotels
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!Lanesborough
9.8 out of 10, Exceptional, (281 reviews)
"The property is very nice, well stocked amenities. Cozy and warm and perfect for a long weekend getaway. "
Jonathan H.
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 InnHancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
John F.
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)
"Cozy spot with lots of thoughtful details. "
Michelle Y.
The price is €229
includes taxes & fees
14 Jun - 15 Jun
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 DenDover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
Tania J.
The price is €284
includes taxes & fees
14 Jun - 15 Jun
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."
Jon
The price is €272
includes taxes & fees
22 Jun - 23 Jun
Perfect for a peaceful get away in clean fresh Vermont air!
Perfect for a peaceful get away in clean fresh Vermont air!Woodford
10.0 out of 10, Exceptional, (82 reviews)
"We had the most wonderful stay! The house and the property were beautiful, the amentities were excellent, and Linda Jane was an incredibly generous and accommodating host. We visit Bennington every year for Thanksgiving with family and we hope to rent with Linda Jane again in the future."
Karissa A.
The price is €318
includes taxes & fees
9 Jun - 10 Jun
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 CollinsvilleCollinsville
10.0 out of 10, Exceptional, (65 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
Mike
The price is €427
includes taxes & fees
8 Jun - 9 Jun
rural, serene + sophisticated space
rural, serene + sophisticated spaceRed Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
BRIAN PATRICK M.
The price is €352
includes taxes & fees
16 Jun - 17 Jun
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
Holiday Inn & Suites Pittsfield-Berkshires by IHG
8/10 Good
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