Find Romantic Hotels in Great Barrington, MA

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Check availability on Great Barrington Romantic Hotels

Tonight
Jan 24 - Jan 25
Tomorrow
Jan 25 - Jan 26
Next weekend
Jan 30 - Feb 1
In two weeks
Feb 6 - Feb 8

Our top choices for Great Barrington romantic hotels

Front of property

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (135 reviews)
"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 NT$5,857
NT$6,425 total
includes taxes & fees
Feb 1 - Feb 2
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, (1,011 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is NT$2,926
NT$3,268 total
includes taxes & fees
Feb 1 - Feb 2
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, (1,001 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is NT$3,099
NT$3,462 total
includes taxes & fees
Jan 30 - Jan 31
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Deluxe Room, 1 King Bed, Ensuite (2nd Floor) | Premium bedding, individually decorated, individually furnished, desk

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (109 reviews)
"Great experience, looking forward to staying again."
United States
Greg
The price is NT$4,421
NT$4,951 total
includes taxes & fees
Jan 26 - Jan 27
Changing Times Boutique Country Lodging
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (844 reviews)
"So charming, clean, thoughtful touches and a really special place!"
United States
Juliana
The price is NT$2,788
NT$3,114 total
includes taxes & fees
Jan 26 - Jan 27
Berkshires Untold
Porch

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very Good, (276 reviews)
"It is so pretty and the views around the hotel were amazing. "
United States
Noraida
The price is NT$5,655
NT$6,504 total
includes taxes & fees
Jan 25 - Jan 26
Interlaken Inn & Resort
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,006 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is NT$5,021
NT$7,019 total
includes taxes & fees
Feb 22 - Feb 23
The Red Lion Inn
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (167 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is NT$5,190
NT$5,968 total
includes taxes & fees
Feb 10 - Feb 11
Blackberry River Inn
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.0 out of 10, Very Good, (12 reviews)
"Antonia was wonderful and made our stay special. She was kind and warm and when we were initially unhappy with our room immediately rectified the situation and in the end our stay was perfect! It’s a charming hotel, clean and centrally located, walking distance to all the local shops in town."
United States
Jamie
The price is NT$5,090
NT$5,758 total
includes taxes & fees
Jan 25 - Jan 26
The Millerton 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.
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
"generally good"
jonathan 1-night trip
Posted 5 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Absolutely fabulous!"
Lisa 1-night trip
Posted 3 weeks ago
The Red Lion Inn

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.

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