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

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Check availability on Great Barrington Romantic Hotels

Tonight
Aug 31 - Sep 1
Tomorrow
Sep 1 - Sep 2
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Our top choices for Great Barrington romantic hotels

A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.
A dog lying on a stone wall in a forested area.
A house with a brick exterior, a green roof, and a driveway leading to a garage.
A modern kitchen with white cabinets, a granite countertop, and a central island with stools.

1. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Maya H.
￥23,969
￥36,591 total
includes taxes & fees
Sep 30 - Oct 1
Berkshire Village Carriage House - Super Private!!
A hot tub under a pergola with string lights, surrounded by a patio area with chairs and an umbrella.
A hotel room with a large bed, a small table with a chair, and a window with curtains.
A house with a wooden front porch, a metal gate, and a sign that reads "Haven at Highlandlake."
A living room with a fireplace, a television mounted on the wall, a sofa, and a small round ottoman.

2. Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
United States
Steve
￥20,171
￥38,405 total
includes taxes & fees
Sep 2 - Sep 3
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
A stone cottage with a turquoise door, a sign reading 'Windy Top Cottage,' and flower boxes on the windows.
A cozy living room with a stone wall, a fireplace, and a chandelier.
A staircase with a stone wall on one side and a wooden handrail on the other.
A bedroom with a bed, nightstands, a dresser, a mirror, and framed pictures on the wall.

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

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
United States
Kristen S.
￥21,572
￥40,307 total
includes taxes & fees
Sep 9 - Sep 10
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
A rustic interior with wooden beams, multiple windows, and a kitchen area with dishes and a coffee maker.
A spacious living area with a fireplace, a dining table, and a kitchen area with wooden cabinets and a stove.
A rustic kitchen with wooden shelves, a gas stove, an oven, and a microwave.
A loft-style room with a wooden ceiling, exposed beams, and a view of the outside through large windows.

4. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
United States
BRIAN PATRICK M.
￥51,069
￥65,445 total
includes taxes & fees
Sep 8 - Sep 9
rural, serene + sophisticated space
A modern kitchen with white cabinets, a large island, and a skylight.
A two-story house with a gravel driveway leading to a garage.
A wooden cabin with a deck and stone steps, surrounded by a grassy area and trees.
A cozy living room with a stone fireplace, a blue sofa, and a mounted deer head.

5. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
United States
Hessie S.
￥142,213
￥234,631 total
includes taxes & fees
Sep 3 - Sep 4
A Country Lodge Straight Out of the Pages of a Great Novel
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Top Great Barrington Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"The Red Lion Inn is always charming and comfortable!"
Maureen R 1-night trip
Posted 5 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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