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

Great Barrington Hotel Guide - Romantic Hotels in Great Barrington, Massachusetts

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Check availability on Great Barrington Romantic Hotels

Tonight
1 Sept - 2 Sept
Tomorrow
2 Sept - 3 Sept
This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

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 modern kitchen with white cabinets, a granite countertop, and a central island with stools.
A house with a brick exterior, a green roof, and a driveway leading to a garage.

1. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Maya H.
€203
includes taxes & fees
16 Sept - 17 Sept
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 living room with a fireplace, a television mounted on the wall, a sofa, and a small round ottoman.
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."

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
€212
includes taxes & fees
2 Sept - 3 Sept
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 fireplace, leather sofas, a wooden coffee table, 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.
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 loft-style room with a wooden ceiling, exposed beams, and a view of the outside through large windows.
A rustic kitchen with wooden shelves, a gas stove, an oven, and a microwave.
A spacious living area with a fireplace, a dining table, and a kitchen area with wooden cabinets and a stove.

4. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
United States
BRIAN PATRICK M.
€347
includes taxes & fees
8 Sept - 9 Sept
rural, serene + sophisticated space
A modern kitchen with white cabinets, a large island, and a skylight.
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.
A bedroom with a large bed, built-in bookshelves, a bedside table, and a window with curtains.

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.
€1,256
includes taxes & fees
3 Sept - 4 Sept
A Country Lodge Straight Out of the Pages of a Great Novel
View all properties

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 8 hours ago
The Red Lion Inn

Frequently asked questions

Searching for romantic hotels in Great Barrington?
If you and your partner need a romantic holiday, 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 neighbourhood or distance to top sights, 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, take a look at these details about year-round temperatures in Great Barrington: The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Great Barrington are January, March, February and November, with each month seeing an average of 18 cm of snowfall.
What is there to do in Great Barrington?
There's nothing better than experiencing 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, theatre 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 in Pittsfield, MA (PSF-Pittsfield Municipal), located 16.2 mi (26.1 km) from the city centre. If you'd like to venture out around the area, consider renting a car to explore more sights.

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