A large stone church with a tall bell tower and arched windows.

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Check availability on Great Barrington Romantic Hotels

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Great Barrington romantic hotels

A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.
A modern living room with a grey sofa, a wooden coffee table, and a dining area with a round table and chairs.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A sign for East Rock Inn with a mountainous logo, surrounded by lush greenery and a gravel path leading to a building.

1. East Rock Inn

East Rock Inn
Great Barrington
United States
Sharon
￥19,001
￥21,224 total
includes taxes & fees
Nov 17 - Nov 18
East Rock Inn
A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.
A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.
A wooden cabin with a bed, a chair, and a table by a large window overlooking a lake.

2. Prospect Berkshires

Prospect Berkshires
Egremont
United States
Conor
￥43,195
￥53,546 total
includes taxes & fees
Nov 4 - Nov 5
Prospect Berkshires
A dining area with round tables set for two, a fireplace, and a mural on the wall.
A room with a leather armchair, a table with a potted plant, a lamp, and a fireplace with decorative elements.
A room with two brown leather armchairs, a wooden side table with a lamp, a potted plant, and a window with a view of a snowy landscape.
A cozy room with a fireplace, wooden walls, a bed with a patterned bedspread, and two wall-mounted lamps.

3. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
United States
Catherine
￥45,826
￥55,298 total
includes taxes & fees
Nov 2 - Nov 3
The Old Inn On The Green
A modern kitchen with a central island, wooden beams, and a view to the outdoors.
A cabin with a wooden deck and a stone pathway leading to the entrance.
A staircase with wooden steps and a wall-mounted table with two chairs.
A modern interior with a wooden staircase, a dining area with stools, a sofa, and a kitchen in the background.

4. Home in Great Barrington

Home in Great Barrington
Great Barrington
United States
Janet G.
￥36,408
￥56,552 total
includes taxes & fees
Oct 26 - Oct 27
Home in Great Barrington
A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.
A wooden fire pit surrounded by six Adirondack chairs in a forested area.
A poolside area with lounge chairs and blue umbrellas, surrounded by a forested area.
A cozy room with a wooden bench, a table with a pitcher, and a sofa with patterned cushions. Large windows with yellow blinds offer a view of greenery outside.

5. Little Cat Lodge

Little Cat Lodge
Copake Falls
United States
Stacy
￥22,352
￥25,034 total
includes taxes & fees
Nov 17 - Nov 18
Little Cat Lodge
A dining table with pastries, a coffee pot, and a vase of sunflowers.
A small cabin with two Adirondack chairs in a grassy field, surrounded by trees and a mountain in the background.
A large, two-story white building with a symmetrical facade, columns, and a central entrance.
A bedroom with a wooden bed, bedside tables, a desk, and a chair.

6. Granville House

Granville House
Housatonic
United States
Cynthia
￥40,157
￥44,856 total
includes taxes & fees
Oct 25 - Oct 26
Granville House
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

7. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
￥15,589
￥17,412 total
includes taxes & fees
Oct 21 - Oct 22
The Yankee Inn
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.
A dining area with large windows, wooden furniture, and a view of a lake.
A lodge with a large building and a dock by a lake, surrounded by forest.
A lakeside dock with kayaks and a covered boat ramp.

8. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Gustavo
￥18,008
￥20,115 total
includes taxes & fees
Nov 15 - Nov 16
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A red building with a sign reading "Shaker Mill Inn."
A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.
A cozy room with a bed, a sofa, a small table, and a desk. There are two lamps on the bed and a window with curtains.
A cozy living room with a sofa, a small table, and a bookshelf. There is a window with curtains, and a painting on the wall.

9. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Steven
￥19,753
￥21,669 total
includes taxes & fees
Nov 16 - Nov 17
Shaker Mill Inn
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A bar with wooden floors and shelves filled with bottles.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

10. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
￥24,891
￥35,653 total
includes taxes & fees
Nov 16 - Nov 17
The Red Lion Inn
View all properties

Top Great Barrington Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This place is a must stay! We loved every bit of it and had a best time!!! Def recommend 100%"
Hope 1-night trip
Posted 8 hours 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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