Find Romantic Hotels in Great Barrington, MA

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Check availability on Great Barrington Romantic Hotels

Tonight
4 Dec - 5 Dec
Tomorrow
5 Dec - 6 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Great Barrington Romantic Hotels

Front of property
Gedney Farm

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
The price is SAR 696
SAR 764 total
includes taxes & fees
10 Dec - 11 Dec
Gedney Farm
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Great stay!"
United States
Ann
The price is SAR 235
SAR 262 total
includes taxes & fees
14 Dec - 15 Dec
The Yankee, Trademark Collection by Wyndham
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (976)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is SAR 348
SAR 389 total
includes taxes & fees
17 Dec - 18 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Outdoor pool, sun loungers
The Red Lion Inn

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
The price is SAR 446
SAR 665 total
includes taxes & fees
4 Jan - 5 January 2026
The Red Lion Inn
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (806)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is SAR 411
SAR 460 total
includes taxes & fees
7 Dec - 8 Dec
Berkshires Untold
Library
Blackberry River Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (162)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is SAR 617
SAR 709 total
includes taxes & fees
18 Dec - 19 Dec
Blackberry River Inn
Porch
Interlaken Inn & Resort

Interlaken Inn & Resort

3.5 star property
Lakeville
8.2 out of 10, Very Good, (270)
"The staff is courteous and accommodating especially the restaurant staff."
United States
Christian
The price is SAR 782
SAR 899 total
includes taxes & fees
6 Dec - 7 Dec
Interlaken Inn & Resort
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!

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.
The price is SAR 507
SAR 792 total
includes taxes & fees
8 Dec - 9 Dec
Berkshire Village Carriage House - Super Private!!
Balcony
The Nest Hudson

The Nest Hudson

3.5 star property
Hudson
9.6 out of 10, Exceptional, (209)
"What a beautiful stay right in the heart of Hudson. Cute, cozy, super clean with everything you need! "
United States
Kseniya
The Nest Hudson
Room (King Room) | Iron/ironing board, free WiFi, bed sheets
Gateways Inn & Restaurant

Gateways Inn & Restaurant

3.0 star property
Lenox
8.0 out of 10, Very Good, (192)
"Very well kept property, nice restaurant and is in a great area"
United States
Josephine
The price is SAR 621
SAR 725 total
includes taxes & fees
4 Jan - 5 January 2026
Gateways Inn & Restaurant
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.
View all properties

Top Great Barrington Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Everything was great. "
Mosaddeq 2-night trip
Posted 10 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"I love the ambience - historic and comfortable and excellent food. "
Nancy 1-night trip
Posted 1 month ago
The Red Lion Inn

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Frequently asked questions

Searching for romantic hotels in Great Barrington?
If you and your partner need some romantic time away, we've got just the ticket. Our guests also love Great Barrington for its hiking, skiing, and array of dining options. If you want to explore the area, you might head to Housatonic River Walk, Housatonic River, or Mahaiwe Performing Arts Center. If you're interested in staying near a certain attraction, you can sort properties by neighborhood or distance to top landmarks, so you and your partner will get to see everything on your list.
When is the best time of year for a romantic getaway to Great Barrington?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Great Barrington: The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Great Barrington are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in Great Barrington?
There's nothing better than seeing a new destination with your sweetheart, so consider taking time to discover all that Great Barrington has to offer. Couples looking for a little of everything will enjoy Great Barrington for its live music, theater scene, and restaurants. You might consider a visit to Housatonic River Walk, Housatonic River, or Mahaiwe Performing Arts Center.
What's the best way to get to Great Barrington and around town during my romantic getaway?
This information about transportation options in Great Barrington might help your romantic trip get off to a smooth start: If you're looking to fly to Great Barrington, the closest major airport is Pittsfield, MA (PSF-Pittsfield Municipal), located 16.2 mi (26.1 km) from the city center. If you'd like to venture out around the area, you may want to rent a car for your trip.