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Find Romantic Hotels in The Berkshires, MA

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Check availability on The Berkshires Romantic Hotels

Tonight
Sep 14 - Sep 15
Tomorrow
Sep 15 - Sep 16
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for The Berkshires romantic hotels

1. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Maya H.
¥20,737
¥32,430 total
includes taxes & fees
Sep 16 - Sep 17
Berkshire Village Carriage House - Super Private!!

2. 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
United States
John F.
¥14,793
¥34,369 total
includes taxes & fees
Sep 15 - Sep 16
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

3. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
United States
Jennifer O.
¥35,177
¥73,953 total
includes taxes & fees
Sep 15 - Sep 16
A roomy remodeled retreat close to MassMoCA

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

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
United States
Kristen S.
¥20,737
¥37,980 total
includes taxes & fees
Sep 20 - Sep 21
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

5. 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
United States
Tania J.
¥8,295
¥46,866 total
includes taxes & fees
Sep 21 - Sep 22
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

6. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
United States
Christine P.
¥21,966
¥43,395 total
includes taxes & fees
Sep 15 - Sep 16
2 Bed Berkshire Apt minutes to Jiminy Peak Ski

7. 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
United States
Anita T.
¥28,894
¥60,886 total
includes taxes & fees
Sep 15 - Sep 16
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

8. 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
United States
Mike
¥43,134
¥74,619 total
includes taxes & fees
Sep 17 - Sep 18
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

9. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
¥49,923
¥86,710 total
includes taxes & fees
Oct 1 - Oct 2
Gorgeous Mountain Views Retreat: Family & Nature

10. Experience Vermont’s Fall Magic at here at the Lemondrop

Experience Vermont’s Fall Magic at here at the Lemondrop
Dover
United States
Alexander H.
¥49,002
¥98,246 total
includes taxes & fees
Sep 23 - Sep 24
Experience Vermont’s Fall Magic at here at the Lemondrop
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Find out more about The Berkshires

The Berkshires attractions for couples

The Berkshires beckon with a blend of culture, nature, and adventure, perfect for the discerning traveler seeking quality experiences. Start your journey at Tanglewood, the summer home of the Boston Symphony Orchestra, where you can enjoy world-class music amid breathtaking natural scenery. For art enthusiasts, the Norman Rockwell Museum in Stockbridge offers an intimate look at the beloved artist's life and works, set against the charming backdrop of New England. Families can explore the interactive exhibits at the Berkshire Museum in Pittsfield, which combines art, history, and science to engage visitors of all ages. Outdoor lovers will relish a hike in the scenic Mount Greylock State Reservation, where the highest peak in Massachusetts provides stunning panoramic views and serene trails. After a day of exploration, consider staying in Lenox, where luxury hotels like the 19th-century Blantyre estate offer a unique blend of historic charm and modern comforts, ensuring attentive service and a pampered experience. The blend of activities and high-end accommodations in The Berkshires creates an enjoyable getaway that caters to your every need.

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"Our suite was quite spacious"
Dereck 2-night trip
Posted 3 hours ago
Vacation Village in the Berkshires
The Red Lion Inn

The Red Lion Inn

8/10 Good
"We stopped at the red lion Inn on our travels back home from Maine. Our room was a block away from the main building and in an old house. It was very clean and comfortable. The location in town is nice."
Guy 1-night trip
Posted 9 hours ago
The Red Lion Inn

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