A mountainous landscape with a lake and dense forests.

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Check availability on West Stockbridge Romantic Hotels

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

Our top choices for West Stockbridge romantic hotels

A red building with a sign reading "Shaker Mill Inn."

1. Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (482 reviews)
"Loved the location, fireplace and vibe"
United States
Mahadeva
The price is AED 419
AED 459 total
includes taxes & fees
2 Nov - 3 Nov
Shaker Mill Inn
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,013 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"
United States
Gustavo
The price is AED 403
AED 450 total
includes taxes & fees
22 Nov - 23 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

3. The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,003 reviews)
"Enjoyed staying in the old hotel and loved the large porch with the bar to relax on."
United States
Mallory
The price is AED 562
AED 810 total
includes taxes & fees
4 Nov - 5 Nov
The Red Lion Inn
Two Adirondack chairs facing a river with a forested hill in the background.

4. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,006 reviews)
"The location was good for our trip."
United States
Basil
The price is AED 355
AED 396 total
includes taxes & fees
20 Nov - 21 Nov
The Yankee Inn
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

5. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,053 reviews)
"A very good place to stay"
United States
Madhavi R
The price is 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.

6. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is AED 624
AED 716 total
includes taxes & fees
1 Nov - 2 Nov
The Cornell Inn, Lenox & The Berkshires
Dining

7. Garden Gables

Garden Gables
4.0 star property
Lenox
The price is AED 512
AED 838 total
includes taxes & fees
29 Oct - 30 Oct
Garden Gables
A two-story house with a brick entrance and a white facade.

8. 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
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (120 reviews)
"The property is conveniently located for access to Stockbridge, Lenox, and Tanglewood."
United States
Philippe
The price is AED 1,234
AED 1,493 total
includes taxes & fees
27 Nov - 28 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.

9. Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (118 reviews)
"Perfect location for hiking, hanging out and Tanglewood Comfortable and charming common space and cozy nicely decorated rooms Generous breakfast and snacks throughout the day We’ll be back"
United States
Linda
The price is AED 676
AED 757 total
includes taxes & fees
22 Nov - 23 Nov
Inn at Silver Maple Farm
A dining table with pastries, a coffee pot, and a vase of sunflowers.

10. Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (110 reviews)
"We loved everything about Granville House, especially the innkeepers! Wonderful atmosphere and excellent food! It was definitely the highlight of our trip to New England."
United States
Cynthia
The price is AED 937
AED 1,046 total
includes taxes & fees
1 Nov - 2 Nov
Granville House
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top West Stockbridge Hotel Reviews

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Rooms were clean, nice beds and new kitchen accessories."
Linda 1-night trip
Posted 1 day ago
Jiminy Peak Mountain Resort

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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