The Best Romantic Hotels in West Stockbridge, MA from AED 386 in 2026

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Our top choices for West Stockbridge romantic hotels

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

1. Shaker Mill Inn

West Stockbridge

Mahadeva

AED 584 total

includes taxes & fees

9 Nov - 10 Nov

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

Lee

Gustavo

AED 439 total

includes taxes & fees

3 Dec - 4 Dec

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

3. The Red Lion Inn

Stockbridge

Lisabeth

AED 829 total

includes taxes & fees

12 Nov - 13 Nov

A hotel room with a bed, a television, a wardrobe, and a bathroom visible through an open door.

4. Garden Gables

Lenox

Eyee

AED 797 total

includes taxes & fees

12 Nov - 13 Nov

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

5. Berkshires Untold

Lenox

Brian

AED 431 total

includes taxes & fees

17 Nov - 18 Nov

Two Adirondack chairs facing a river with a forested hill in the background.

6. The Yankee Inn

Lenox

Basil

AED 452 total

includes taxes & fees

8 Dec - 9 Dec

A snow-covered outdoor area with a patio, seating, and a covered dining area.

7. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

AED 716 total

includes taxes & fees

9 Nov - 10 Nov

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

Stockbridge

Philippe

AED 1,697 total

includes taxes & fees

26 Nov - 27 Nov

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

9. Inn at Silver Maple Farm

East Chatham

Linda

AED 675 total

includes taxes & fees

3 Dec - 4 Dec

A dining table with pastries, a coffee pot, and a vase of sunflowers.

10. Granville House

Housatonic

Cynthia

AED 1,042 total

includes taxes & fees

20 Nov - 21 Nov

View all properties

Top West Stockbridge Hotel Reviews

Shaker Mill Inn

West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Lawrence

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

Brook Farm Inn

Lenox

10/10 Excellent

roberta

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

Devonfield Inn B&B

Lee

10/10 Excellent

Anonymous traveler

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

Stockbridge

10/10 Excellent

Charles

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

10/10 Excellent

Sheila

The Red Lion Inn

Stockbridge

10/10 Excellent

Michael

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

Michelle

The Yankee Inn

Lenox

10/10 Excellent

We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!

Colleen

Berkshires Untold

Lenox

10/10 Excellent

High end feel at a budget friendly price. The room was boho fun but needs a few tweaks. I still give it 5 stars but wish that they had a variety of pillows on the bed, they were very nice but too thick for a stomach or back sleeper. There is a full mini bar with prices only available by QR reader, there is a free bottle of still water but since it was not marked i wasn’t sure what it was or if it was free. There is a fun wardrobe with robes but no place but the floor to put your suit case. Oh...

Jill

A two-story building with a sign reading "Chambéry Inn".

Chambery Inn

Lee

10/10 Excellent

Elaine

A large, two-story building with a symmetrical facade, multiple windows, and a well-maintained lawn.

Gateways Inn & Restaurant

Lenox

10/10 Excellent

Richard

A rustic interior with wooden tables and chairs, brick walls, and a large wooden beam structure.

Little Cat Lodge

Copake Falls

10/10 Excellent

Elisabeth

Wilder House Berkshires

Sheffield

10/10 Excellent

Liliana

A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

Changing Times Boutique Country Lodging

Craryville

10/10 Excellent

Our second time staying here was even more lovely than the first! We brought more family members after our great experience last year. We love the easy check in, cozy comfortable rooms, lots of extras (books and DVDs in the hallway, sweet treats downstairs and in the rooms) and Loretta is the BEST host! She makes an exquisite breakfast and accommodates our early start time. Can’t wait to stay here again.

Kathleen

A dining area with round tables set for two, a fireplace, and a mural on the wall.

The Old Inn On The Green

Great Barrington

10/10 Excellent

Rishi

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.

Find Romantic Hotels in West Stockbridge, MA

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for West Stockbridge romantic hotels

1. Shaker Mill Inn

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

3. The Red Lion Inn

4. Garden Gables

5. Berkshires Untold

6. The Yankee Inn

7. The Cornell Inn, Lenox & The Berkshires

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

9. Inn at Silver Maple Farm

10. Granville House

Top West Stockbridge Hotel Reviews

Shaker Mill Inn

10/10 Excellent

Frequently Asked Questions

Searching for romantic hotels in West Stockbridge?

When is the best time of year for a romantic getaway to West Stockbridge?

What is there to do in West Stockbridge?

What’s the best way to get to West Stockbridge and around town during my romantic getaway?

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