Find Romantic Hotels in Great Barrington, MA

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Check availability on Great Barrington Romantic Hotels

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct

Top Great Barrington Romantic Hotels

Berkshires Untold
Interior

Berkshires Untold

3.5 star property
9.0 out of 10, Wonderful, (745)
"Great location and very clean. Beautifully decorated and the restaurant is amazing. Just wish it offered a free breakfast with the room. "
The price is AED 321
AED 359 total
includes taxes & fees
5 Nov - 6 Nov
Berkshires Untold
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (139)
"Loved everything especially Lucas and Joe💟☮️"
The price is AED 604
AED 694 total
includes taxes & fees
6 Oct - 7 Oct
Blackberry River Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (891)
"Excellent customer service and great rooms"
The price is AED 378
AED 423 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Gedney Farm
Front of property

Gedney Farm

3.5 star property
9.2 out of 10, Wonderful, (130)
"Great property"
Gedney Farm
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1001)
"Nice area to visit "
The price is AED 493
AED 550 total
includes taxes & fees
2 Nov - 3 Nov
The Yankee, Trademark Collection by Wyndham
Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (259)
"We enjoyed our stay. Excellent location to explore Western Mass!"
The price is AED 551
AED 841 total
includes taxes & fees
28 Oct - 29 Oct
Berkshire Village Carriage House - Super Private!!
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1004)
"great place have stayed several times, and hope to return."
The price is AED 577
AED 809 total
includes taxes & fees
2 Nov - 3 Nov
The Red Lion Inn
Brook Farm Inn
Loft, Private Bathroom (Skylight Loft) | 1 bedroom, premium bedding, iron/ironing board, rollaway beds

Brook Farm Inn

3.5 star property
9.4 out of 10, Exceptional, (161)
"Inn was gorgeous and staff exceptional!"
Brook Farm Inn
Interlaken Inn & Resort
Porch

Interlaken Inn & Resort

3.5 star property
8.2 out of 10, Very Good, (265)
"The staff is courteous and accommodating especially the restaurant staff."
The price is AED 741
AED 852 total
includes taxes & fees
27 Oct - 28 Oct
Interlaken Inn & Resort
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (325)
"Great spot. Lots of history. "
The price is AED 673
AED 751 total
includes taxes & fees
29 Oct - 30 Oct
The Dewey
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great place! Food excellent ss well!"
Crystal 1-night trip
Posted 5 days ago
The Red Lion Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Valerie at the front desk and who checked me in was above and beyond in customer service. She checked to see if I had a IGH account—which I did but had forgotten, and reminded me about the points and promotions. This Holiday Inn is a well managed property. Thank you"
Carin 1-night trip
Posted 3 weeks ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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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.