Find Romantic Hotels in Great Barrington, MA

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Pick from 4 Great Barrington Romantic Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

The Old Inn On The Green
Room

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (79)
"There is a high-end restaurant at the Inn that has wonderful food. Delicious breakfasts (and Sunday Brunch) down the road at The Southfield Store were included. You can take a lovely back road walk past a beaver pond that starts from the parking lot. Employees were friendly and helpful. Multiple other protected area hikes in the neighborhood. We felt we lucked out picking this place."
The price is AED 973
AED 1,132 total
includes taxes & fees
25 Nov - 26 Nov
The Old Inn On The Green
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.
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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.
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.