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Find Romantic Hotels in The Berkshires, MA

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Check availability on The Berkshires Romantic Hotels

This weekend
26 Jun - 28 Jun
Next weekend
3 Jul - 5 Jul

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, (284 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 661
AED 985 total
includes taxes & fees
29 Jun - 30 Jun
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 476
AED 979 total
includes taxes & fees
29 Jun - 30 Jun
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Property grounds

Enjoy comfortable elegance in this secluded grand home located in town

Enjoy comfortable elegance in this secluded grand home located in town
Lenox
10.0 out of 10, Exceptional, (79 reviews)
"Amazing property, close to town "
United States
Tricia E.
The price is AED 2,204
AED 2,814 total
includes taxes & fees
19 Jul - 20 Jul
Enjoy comfortable elegance in this secluded grand home located in town
Exterior

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, (109 reviews)
"Cozy spot with lots of thoughtful details. "
United States
Michelle Y.
The price is AED 496
AED 923 total
includes taxes & fees
8 Jul - 9 Jul
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Terrace/patio

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.2 out of 10, Wonderful, (47 reviews)
The price is AED 579
AED 919 total
includes taxes & fees
2 Jul - 3 Jul
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
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 250
AED 1,200 total
includes taxes & fees
28 Jun - 29 Jun
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, (106 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 474
AED 1,178 total
includes taxes & fees
27 Jul - 28 Jul
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!
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, (66 reviews)
The price is AED 1,146
AED 1,927 total
includes taxes & fees
29 Jun - 30 Jun
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Beach

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very Good, (12 reviews)
"Great location and property. thank you"
United States
Christine P.
The price is AED 545
AED 1,055 total
includes taxes & fees
1 Jul - 2 Jul
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Exterior

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, (83 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."
United States
Karissa A.
The price is AED 628
AED 1,415 total
includes taxes & fees
30 Jun - 1 Jul
Perfect for a peaceful get away in clean fresh Vermont air!
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
"Wonderful historic hotel. Beautiful property and absolutely lovely pool."
Suzanne 2-night trip
Posted 5 hours ago
The Red Lion Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"The hotel is getting a new parking garage so parking was at a premium. But the FREE valet service makes it worthwhile for sure. The rooms were extremely clean, comfortable and quiet. The buffet breakfast in the morning is top-notch and everyone I spoke to was very helpful accommodating, and truly acting like they enjoyed their job. I was traveling with my teen daughter and we felt safe and well taken care of staying here. Thank you for a wonderful stay at your place. Will definitely book here again next time in area."
Heather 2-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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