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Find Romantic Hotels in The Berkshires, MA

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Check availability on The Berkshires Romantic Hotels

Tonight
1 Sep - 2 Sep
Tomorrow
2 Sep - 3 Sep
This weekend
4 Sep - 6 Sep
Next weekend
11 Sep - 13 Sep

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.
AED 551
AED 845 total
includes taxes & fees
16 Sep - 17 Sep
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.
AED 459
AED 956 total
includes taxes & fees
2 Sep - 3 Sep
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.
AED 841
AED 1,781 total
includes taxes & fees
9 Sep - 10 Sep
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.
AED 496
AED 927 total
includes taxes & fees
8 Sep - 9 Sep
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

5. 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
United States
Steve
AED 463
AED 881 total
includes taxes & fees
2 Sep - 3 Sep
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

6. 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.
AED 179
AED 1,111 total
includes taxes & fees
2 Sep - 3 Sep
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

7. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
United States
Christine P.
AED 566
AED 1,093 total
includes taxes & fees
2 Sep - 3 Sep
2 Bed Berkshire Apt minutes to Jiminy Peak Ski

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
AED 1,146
AED 1,942 total
includes taxes & fees
10 Sep - 11 Sep
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

9. 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.
AED 691
AED 1,452 total
includes taxes & fees
8 Sep - 9 Sep
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

10. Summer Escape Near Lakes, Trails & Mt Snow

Summer Escape Near Lakes, Trails & Mt Snow
Dover
United States
william k.
AED 645
AED 1,712 total
includes taxes & fees
2 Sep - 3 Sep
Summer Escape Near Lakes, Trails & Mt Snow
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Top The Berkshires Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"The Red Lion Inn is always charming and comfortable!"
Maureen R 1-night trip
Posted 13 hours ago
The Red Lion Inn
The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Lovely people and place. Breakfast was great and so was the room. Highly recommend."
FRED 1-night trip
Posted 18 hours ago
The Cornell Inn, Lenox & The Berkshires
Willows Motel Williamstown

Willows Motel Williamstown

10/10 Excellent
"Our one-night stay at Willows Motel was very pleasant. The staff/managers/owners were friendly and helpful, our room was comfortable and clean. We were easily able to control the temperature with up-to-date air conditioning. The free continental breakfast was healthy and generous, including a plentiful assortment of fruits, nuts, dates, etc. to accompany the cereal, breads, bagels, etc. We also appreciated the well-kept small garden areas around the property. We would choose the Willows Motel again if we are staying in the Williamstown area."
Carol 1-night trip
Posted 2 days ago
Willows Motel Williamstown
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Nice to have a kitchenette to cook in"
Jacqueline 1-night trip
Posted 2 days ago
Jiminy Peak Mountain Resort

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