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
  • Be picky

    Search almost a million properties worldwide

Check availability on The Berkshires Romantic Hotels

Our top choices for The Berkshires romantic hotels

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (288 reviews)
"This place was really great! Better than the photos. Clean and cute and quiet."
United States
Adam J
The price is AED 661
AED 981 total
includes taxes & fees
28 Jul - 29 Jul
Berkshire Village Carriage House - Super Private!!

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 407
AED 889 total
includes taxes & fees
27 Jul - 28 Jul
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (57 reviews)
"Comfortable lovely home with everything we needed to have a great weekend. "
United States
Margaret C.
The price is AED 841
AED 1,781 total
includes taxes & fees
4 Aug - 5 Aug
A roomy remodeled retreat close to MassMoCA

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, (111 reviews)
"We loved our stay! The cottage was adorable!"
United States
Kristen S.
The price is AED 496
AED 916 total
includes taxes & fees
2 Aug - 3 Aug
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

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
9.4 out of 10, Exceptional, (48 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is AED 579
AED 926 total
includes taxes & fees
26 Jul - 27 Jul
Enjoy a restful stay with fast internet, smart TV and the company of your pet.

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 566
AED 1,089 total
includes taxes & fees
26 Jul - 27 Jul
2 Bed Berkshire Apt minutes to Jiminy Peak Ski

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, (107 reviews)
"This is the third time we’ve stayed at this lovely home and it’s always a treat! Very clean, with a Well stocked kitchen, comfy beds and huge back yard plus a fenced in portion, your dog will love-close to Bennington and walking trails with lots to do. A home away from home! "
United States
Anita T.
The price is AED 691
AED 1,476 total
includes taxes & fees
27 Jul - 28 Jul
Cozy Summer retreat with great Pet 🦮 Yard and upgrades! Close to hiking areas!

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, (68 reviews)
"What a wonderful spot and exceptional host. Loved our stay and hope to visit again soon. "
United States
Mike
The price is AED 1,146
AED 1,931 total
includes taxes & fees
30 Jul - 31 Jul
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville

Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (129 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is AED 1,107
AED 2,051 total
includes taxes & fees
30 Jul - 31 Jul
Gorgeous Mountain Views Retreat: Family & Nature

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 746
AED 1,843 total
includes taxes & fees
31 Jul - 1 Aug
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
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.

Top The Berkshires Hotel Reviews

Explore a world of travel with Expedia