A mountainous landscape with a lake and dense forests.

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Check availability on West Stockbridge 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 West Stockbridge romantic hotels

A red building with a sign reading "Shaker Mill Inn."
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 stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.
A covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.

1. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Steven
AED 459
AED 504 total
includes taxes & fees
16 Nov - 17 Nov
Shaker Mill Inn
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A covered porch with wicker furniture and hanging flower baskets.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

2. The Red Lion Inn

The Red Lion Inn
Stockbridge
United States
Stephan
AED 579
AED 829 total
includes taxes & fees
4 Nov - 5 Nov
The Red Lion 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 lakeside dock with kayaks and a covered boat ramp.
A lakeside lodge with a dock, fishing rods, and outdoor seating.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Gustavo
AED 418
AED 467 total
includes taxes & fees
15 Nov - 16 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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 hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
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.

4. The Yankee Inn

The Yankee Inn
Lenox
United States
Basil
AED 333
AED 372 total
includes taxes & fees
27 Oct - 28 Oct
The Yankee Inn
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".
A cozy library with bookshelves, a fireplace, and comfortable seating.
A spacious bar area with a long counter and multiple stools, a seating area with a sofa and chairs, and a view through large windows to the outdoors.

5. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
AED 478
AED 534 total
includes taxes & fees
1 Nov - 2 Nov
Berkshires Untold
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.
A dining area with a glass table, red walls, and framed artwork.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.

6. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United Kingdom
judith
AED 564
AED 647 total
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
A two-story house with a brick entrance and a white facade.
A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A neatly arranged bedroom with a bed, bedside table, and a dresser.

7. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Stockbridge
United States
Philippe
AED 1,375
AED 1,663 total
includes taxes & fees
4 Nov - 5 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.
A spacious kitchen with wooden beams, a dining area with a large table and chairs, and a view of the outdoors through large windows.
A wooden interior with a table, chair, and a view of a red barn through an open door.
A spacious living room with a high ceiling, wooden beams, a fireplace, and a bookshelf filled with books.

8. Inn at Silver Maple Farm

Inn at Silver Maple Farm
East Chatham
United States
Linda
AED 639
AED 716 total
includes taxes & fees
8 Nov - 9 Nov
Inn at Silver Maple Farm
A dining table with pastries, a coffee pot, and a vase of sunflowers.
A pool table in a room with a patterned rug, a shelf with decorative items, and a window with a view of greenery.
A bedroom with a wooden bed, bedside tables, a desk, and a chair.
A small cabin with two Adirondack chairs in a grassy field, surrounded by trees and a mountain in the background.

9. Granville House

Granville House
Housatonic
United States
Cynthia
AED 933
AED 1,042 total
includes taxes & fees
25 Oct - 26 Oct
Granville House
A large, two-story house with a well-maintained lawn and a fence.
A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.
A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

10. Devonfield Inn B&B

Devonfield Inn B&B
Lee
United States
Sebastien
AED 1,355
AED 1,514 total
includes taxes & fees
2 Nov - 3 Nov
Devonfield Inn B&B
View all properties

Top West Stockbridge 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 11 hours ago
The Red Lion Inn

Frequently asked questions

Searching for romantic hotels in West Stockbridge?
Are you looking for a romantic vacation? Our guests also enjoy West Stockbridge for its restaurants and gardens. If you want to explore the area, you might head to Stockbridge Bowl, Charles H. Baldwin & Sons, or Ebenezer II Gifts and Antiques. If you're interested in staying near a certain attraction, you can sort properties by neighborhood 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 West Stockbridge?
If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in West Stockbridge: 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 27°F. The snowiest months in West Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What is there to do in West Stockbridge?
There's nothing better than wandering around a new place with your sweetheart, so consider taking time to discover all there is to see and do in West Stockbridge. Couples looking to get out in nature will enjoy West Stockbridge for its gardens. You might think about stopping by Stockbridge Bowl, Charles H. Baldwin & Sons, or Ebenezer II Gifts and Antiques while you're seeing the sights.
What's the best way to get to West Stockbridge and around town during my romantic getaway?
This information about transportation options in West Stockbridge might help your romantic trip get off to a smooth start: Make your way to West Stockbridge with a flight to Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest major airport located 7.4 mi (11.9 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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