A person snowboarding down a snowy slope.

Find Romantic Hotels in The Berkshires, MA

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Romantic Hotels

Tonight
7 Aug - 8 Aug
Tomorrow
8 Aug - 9 Aug
This weekend
7 Aug - 9 Aug
Next weekend
14 Aug - 16 Aug

Our top choices for The Berkshires romantic hotels

1. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Adam J
AED 551
AED 821 total
includes taxes & fees
31 Aug - 1 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 463
AED 964 total
includes taxes & fees
10 Aug - 11 Aug
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

3. 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 782 total
includes taxes & fees
10 Aug - 11 Aug
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

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 916 total
includes taxes & fees
9 Aug - 10 Aug
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

5. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
Gorgeous Mountain Views Retreat: Family & Nature

6. 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 1,031
AED 1,784 total
includes taxes & fees
10 Aug - 11 Aug
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

7. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
United States
Hessie S.
AED 3,269
AED 5,410 total
includes taxes & fees
17 Aug - 18 Aug
A Country Lodge Straight Out of the Pages of a Great Novel

8. 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 1,089 total
includes taxes & fees
10 Aug - 11 Aug
2 Bed Berkshire Apt minutes to Jiminy Peak Ski

9. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
United States
BRIAN PATRICK M.
AED 1,098
AED 1,374 total
includes taxes & fees
30 Aug - 31 Aug
rural, serene + sophisticated space

10. Perfect for a peaceful get away in clean fresh Vermont air!

Perfect for a peaceful get away in clean fresh Vermont air!
Woodford
United States
Karissa A.
AED 698
AED 1,497 total
includes taxes & fees
31 Aug - 1 Sep
Perfect for a peaceful get away in clean fresh Vermont air!
View all properties

Top The Berkshires Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"Property is aging and needs attention. Still a nice place to stay."
James 4-night trip
Posted 7 hours ago
The Red Lion Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"Breakfast was delayed but the late arriving staff worked quickly to restore it. Quality of food was excellent"
Paul 1-night trip
Posted 13 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Jiminy Peak is located in an absolutely beatiful location in the Berkshires. And it has fun family-friendly summertime activities. But it could use some sprucing up. The pool liner is a little wrinkly and the hot tub is quite stained near the water line. In addition, our room had a nice 2-foot gouge in the wall seemingly caused by the corner of the armchair beneath it. It seems that could/should have been repaired before out arrival. And the dated counertops and fixtures are showing their age. That said, so am I! On the plus side: the iconic scenery, the friendly helpful staff, and the amenities. All in all, a good value for a family getaway. I would definitely recommend the prolerty overall."
Fausto 2-night trip
Posted 1 day ago
Jiminy Peak Mountain Resort

Explore a world of travel with Expedia