Find Romantic Hotels in Great Barrington, MA

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Check availability on Great Barrington Romantic Hotels

Tonight
23 Jun - 24 Jun
Tomorrow
24 Jun - 25 Jun
This weekend
27 Jun - 29 Jun
Next weekend
4 Jul - 6 Jul

Top Great Barrington Romantic Hotels

Gedney Farm
Front of property

Gedney Farm

3.5 star property
9.2 out of 10, Wonderful, (120)
"Great staff. Quiet.. and an excellent chef! Unique property and well worth it!"
Gedney Farm
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Exterior detail

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!

10.0 out of 10, Exceptional, (83)
"Charming cottage, wonderful hosts!!Two over-60 grandmas, one from CT and one from MA met to sit in front of the fire with a cup of tea and catch up. This was the perfect setting to simply retreat and relax. "
The price is SAR 563
SAR 992 total
includes taxes & fees
1 Jul - 2 Jul
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.6 out of 10, Exceptional, (108)
"Very helpful and friendly staff"
The price is SAR 624
SAR 717 total
includes taxes & fees
25 Jun - 26 Jun
Blackberry River Inn
The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.2 out of 10, Wonderful, (1005)
"Nice place to stay. Good breakfast. "
The price is SAR 473
SAR 528 total
includes taxes & fees
30 Jun - 1 Jul
The Yankee, Trademark Collection by Wyndham
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, (796)
"Walking distance from the Colonial Theater, lots of dining options, good breakfast, comfortable bed, clean room, clean hotel."
The price is SAR 409
SAR 457 total
includes taxes & fees
30 Jun - 1 Jul
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Dewey
Exterior

The Dewey

3.5 star property
8.8 out of 10, Excellent, (313)
"Gorgeous place with clean room and excellent areas to have breakfast, read, and relax. Friendly staff and easy checking process. Would stay here again!"
The price is SAR 584
SAR 653 total
includes taxes & fees
30 Jun - 1 Jul
The Dewey
The Constance by the Lenox Collection
Free WiFi, bed sheets

The Constance by the Lenox Collection

3.5 star property
8.6 out of 10, Excellent, (476)
"Staff was incredibly nice & helpful, and the stay was very comfortable. We’d definitely stay there again."
The price is SAR 523
SAR 585 total
includes taxes & fees
30 Jun - 1 Jul
The Constance by the Lenox Collection
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, (152)
"This is a charming and very pleasant place to stay."
Brook Farm Inn
The Red Lion Inn
Outdoor pool, sun loungers

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1001)
"I had excellent stay at the Red Lion Inn "
The price is SAR 652
SAR 896 total
includes taxes & fees
26 Jun - 27 Jun
The Red Lion Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Business center

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

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is SAR 1,290
SAR 1,561 total
includes taxes & fees
25 Jun - 26 Jun
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
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.

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.
How many romantic hotels will we find in Great Barrington?
Expedia has 28 romantic Great Barrington hotels for you to get cozy in.
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.