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Find Romantic Hotels in The Berkshires, MA

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Check availability on The Berkshires Romantic Hotels

Tonight
5 Sept - 6 Sept
Tomorrow
6 Sept - 7 Sept
Next weekend
11 Sept - 13 Sept
In two weeks
18 Sept - 20 Sept

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.
£173
includes taxes & fees
16 Sept - 17 Sept
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.
£185
includes taxes & fees
7 Sept - 8 Sept
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.
£350
includes taxes & fees
9 Sept - 10 Sept
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.
£188
includes taxes & fees
9 Sept - 10 Sept
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.
£232
includes taxes & fees
9 Sept - 10 Sept
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.
£220
includes taxes & fees
8 Sept - 9 Sept
2 Bed Berkshire Apt minutes to Jiminy Peak Ski

7. 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
£393
includes taxes & fees
10 Sept - 11 Sept
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

8. 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.
£293
includes taxes & fees
8 Sept - 9 Sept
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

9. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
United States
BRIAN PATRICK M.
£268
includes taxes & fees
8 Sept - 9 Sept
rural, serene + sophisticated space

10. Summer Escape Near Lakes, Trails & Mt Snow

Summer Escape Near Lakes, Trails & Mt Snow
Dover
United States
Alexander H.
£477
includes taxes & fees
15 Sept - 16 Sept
Summer Escape Near Lakes, Trails & Mt Snow
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Find out more about The Berkshires

The Berkshires attractions for couples

The Berkshires is a paradise of experiences waiting to be explored. Start your adventure at the renowned Tanglewood Music Center, where you can enjoy a summer concert by the Boston Symphony Orchestra amidst the stunning natural backdrop. For art enthusiasts, the Massachusetts Museum of Contemporary Art (MASS MoCA) is a must-visit, showcasing groundbreaking installations and performances in a former mill turned vibrant art hub. Families will delight in a day at the Berkshire Museum, where interactive exhibits and a diverse aquarium offer fun for all ages. Outdoor lovers can hike the picturesque trails of Mount Greylock, the highest peak in Massachusetts, breathtaking panoramic views and well-maintained paths suitable for all skill levels. After a day of exploration, unwind in the charming town of Lenox, known for its luxurious accommodations like the historic Cranwell Spa & Golf Resort. With its elegant rooms and top spa services, it’s the perfect base for a comfortable stay while you delve into the region's rich culture and natural beauty. The Berkshires promises a delightful blend of artistic flair and outdoor adventure, ensuring memorable experiences for the entire family.

Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Enjoyed our stay and would highly recommend!"
Roger 2-night trip
Posted 2 hours ago
Vacation Village in the Berkshires
Willows Motel Williamstown

Willows Motel Williamstown

10/10 Excellent
"Great little motel that was the perfect stay for a quick overnight trip"
Kate 1-night trip
Posted 2 hours ago
Willows Motel Williamstown
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Charming, updated throughout. Extremely clean and well appointed. Extremely delightful stay."
Colleen And mark 2-night trip
Posted 1 day ago
The Red Lion Inn

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