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

Our top choices for Great Barrington romantic hotels

A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.
A spacious kitchen with wooden beams, a dining area with a long table, and a living room with a red sofa and a fireplace.
A covered outdoor deck with a wooden table and a mug, overlooking a forested area.
A house with a covered porch and a well-maintained garden.

1. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
United States
Ofer C.
€587
includes taxes & fees
20 Oct - 21 Oct
Secluded Family Home in Serene Stockbridge Woods
A two-story house with a balcony, a deck, and a view of the surrounding forest.
A modern kitchen with white cabinets and a built-in knife block.
A kitchen with wooden floors, a central island, a stainless steel refrigerator, and pendant lighting.
A modern kitchen with wooden beams, a central island with stools, pendant lighting, and a vase of flowers.

2. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
United States
Anne S.
€521
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
A stone patio with outdoor furniture, a small brick house with a green roof, and a forested area.
A modern kitchen with white cabinets, a granite countertop, and a central island with stools.
A dog lying on a stone wall in a forested area.
A kitchen with white cabinets, a granite countertop, a stainless steel sink, and a red pendant light.

3. Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
United States
Mary R.
€193
includes taxes & fees
22 Oct - 23 Oct
Berkshire Village Carriage House - Super Private!!
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 cozy living room with a stone wall, a fireplace, and a chandelier.
A bedroom with a bed, nightstands, a dresser, a mirror, and framed pictures on the wall.

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

A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
Granby
United States
Kristen S.
€243
includes taxes & fees
2 Nov - 3 Nov
A European Country Getaway ~ 1930s Stone Cottage In Connecticut!
A modern kitchen with white cabinets, a large island, and a skylight.
A bedroom with a large bed, built-in bookshelves, a bedside table, and a window with curtains.
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.

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
stephen r.
€1,294
includes taxes & fees
29 Oct - 30 Oct
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
"Good stay"
Jared 1-night trip
Posted 11 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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