A mountainous landscape with a lake and dense forests.

Find Romantic Hotels in West Stockbridge, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on West Stockbridge Romantic Hotels

Tonight
3 Oct - 4 Oct
Tomorrow
4 Oct - 5 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

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 covered patio with a round glass table and metal chairs, a wooden deck, and a view of trees and hills.
A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.

1. Shaker Mill Inn

Shaker Mill Inn
West Stockbridge
United States
Mervin
AED 507
AED 556 total
includes taxes & fees
3 Nov - 4 Nov
Shaker Mill Inn
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
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.
A covered porch with wicker furniture and hanging flower baskets.

2. The Red Lion Inn

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

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
Lee
United States
Bob
AED 425
AED 474 total
includes taxes & fees
1 Nov - 2 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 hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
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.

4. The Yankee Inn

The Yankee Inn
Lenox
United States
William
AED 389
AED 435 total
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
A snow-covered outdoor area with a patio, seating, and a covered dining area.
A two-story house with a balcony, a brick chimney, and a porch with Adirondack chairs.
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.

5. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
Lenox
United States
Rosann
AED 564
AED 647 total
includes taxes & fees
27 Oct - 28 Oct
The Cornell Inn, Lenox & The Berkshires
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.
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.
A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.
A cozy library with bookshelves, a fireplace, and comfortable seating.

6. Berkshires Untold

Berkshires Untold
Lenox
United States
Madhavi R
AED 484
AED 540 total
includes taxes & fees
1 Nov - 2 Nov
Berkshires Untold
A hotel room with a bed, a desk, and two wall-mounted lamps.
A motel with a flagpole, a blue awning, and a parking lot.
A hotel room with a bed, two bedside tables, a desk, two chairs, and a large window with a view of greenery.
A small kitchenette with a coffee maker, toaster, and cabinets. There is a red and green patterned floor and a plant on the left.

7. Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
Lee
United States
Anna
AED 240
AED 269 total
includes taxes & fees
25 Oct - 26 Oct
Econo Lodge Lee - Great Barrington
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 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.

8. Granville House

Granville House
Housatonic
United States
Nicole
AED 823
AED 919 total
includes taxes & fees
12 Oct - 13 Oct
Granville House
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 cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.

9. 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 1,403
AED 1,697 total
includes taxes & fees
1 Nov - 2 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 spacious living room with a high ceiling, wooden beams, a fireplace, and a bookshelf filled with books.
A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

10. Inn at Silver Maple Farm

Inn at Silver Maple Farm
East Chatham
United States
Erdem
AED 749
AED 839 total
includes taxes & fees
1 Nov - 2 Nov
Inn at Silver Maple Farm
View all properties

Top West Stockbridge Hotel Reviews

Shaker Mill Inn

Shaker Mill Inn

10/10 Excellent
"Everything was just perfect, except for the housekeeper didn’t make the bed and empty the trash"
Scott 2-night trip
Posted 6 days ago
Shaker Mill 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.

Explore a world of travel with Expedia