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Find Romantic Hotels in The Berkshires, MA from $100

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Top The Berkshires Romantic Hotels

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1003)
"Great stay!"
United States
Ann
$89 nightly
The price is $100
Dec 15 - Dec 16
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (982)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$92 nightly
The price is $103
Dec 12 - Dec 13
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (808)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
$113 nightly
The price is $126
Dec 14 - Dec 15
Total with taxes and fees
Berkshires Untold

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
$189 nightly
The price is $212
Dec 18 - Dec 19
Total with taxes and fees
The Red Lion Inn

The Williams Inn

4.0 star property
Williamstown
9.6 out of 10, Exceptional, (548)
"Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!"
United States
Jon
$186 nightly
The price is $208
Dec 9 - Dec 10
Total with taxes and fees
The Williams Inn

Brook Farm Inn

3.5 star property
Lenox
9.4 out of 10, Exceptional, (163)
"Everything was perfect - location and accommodation."
United States
Christopher
$179 nightly
The price is $200
Dec 11 - Dec 12
Total with taxes and fees
Brook Farm Inn

Berkshire Village Carriage House - Super Private!!

Lanesborough
9.8 out of 10, Exceptional, (268)
"The cottage was amazing. Hope to be visit again and again. "
United States
Mark M.
$189 nightly
The price is $211
Dec 8 - Dec 9
Total with taxes and fees
Berkshire Village Carriage House - Super Private!!

Gedney Farm

3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (132)
"We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return."
United States
Lynda
$204 nightly
The price is $224
Jan 5 - Jan 6, 2026
Total with taxes and fees
Gedney Farm

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110)
"Wonderful! Owner/host Diane was friendly, helpful, knowledgeable. Breakfasts awesome with great choices daily. Place was spotless, cozy and classic. So glad we stayed there. "
United States
Robert
$414 nightly
The price is $462
Dec 30 - Dec 31
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Hancock
9.8 out of 10, Exceptional, (20)
"Great place to spend the new years holiday! Perfect location for skiing!"
United States
Alexandra D.
$211 nightly
The price is $236
Dec 8 - Dec 9
Total with taxes and fees
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
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.

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

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