West Stockbridge Holiday Rentals, Massachusetts: Private House Rentals

A mountainous landscape with a lake and dense forests.

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Our top choices for West Stockbridge 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 cozy living room with a sofa, a small table, and a bookshelf. There is a window with curtains, and a painting on the wall.

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

West Stockbridge

Steven

฿4,406

฿4,833 total

includes taxes & fees

9 Nov - 10 Nov

A group of people performing yoga in an outdoor setting with grass and trees.

A motel with a row of rooms, a parking lot, and a hilly backdrop.

A reception desk with a framed floral painting, a deer head, and a sign about pets.

A hotel room with a flat-screen TV, a microwave, a refrigerator, a wooden dresser, a bedside lamp, and a framed picture on the wall.

2. Pleasant Valley Motel West Stockbridge

West Stockbridge

James

฿2,305

฿2,528 total

includes taxes & fees

14 Oct - 15 Oct

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 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.

3. The Red Lion Inn

Stockbridge

Stephan

฿5,298

฿7,588 total

includes taxes & fees

3 Nov - 4 Nov

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

A modern restaurant with wooden flooring, bar area, and seating arrangements.

A covered outdoor area with stone pillars and a view of a road and green hills.

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

4. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

฿4,225

฿4,719 total

includes taxes & fees

1 Nov - 2 Nov

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 dining area with large windows, wooden furniture, and a view of a lake.

A lakeside dock with kayaks and a covered boat ramp.

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

Lee

Gustavo

฿3,859

฿4,311 total

includes taxes & fees

8 Nov - 9 Nov

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 modern living room with a fireplace, comfortable seating, and a large window with curtains.

6. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

฿5,161

฿5,920 total

includes taxes & fees

27 Oct - 28 Oct

A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

A swimming pool with a surrounding deck, a stone wall, and a building in the background.

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.

7. The Yankee Inn

Lenox

Basil

฿3,565

฿3,982 total

includes taxes & fees

1 Nov - 2 Nov

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

A cozy library with bookshelves, a fireplace, and comfortable seating.

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

An outdoor seating area with a sofa, chairs, and tables, and a building with large windows and a door labeled "Hotel Entrance".

8. Berkshires Untold

Lenox

Madhavi R

฿4,379

฿4,891 total

includes taxes & fees

1 Nov - 2 Nov

A spacious hotel lobby with multiple seating areas, large windows, and a television.

A gym with exercise equipment including treadmills, a stationary bike, and free weights.

A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.

9. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

฿3,688

฿4,119 total

includes taxes & fees

1 Nov - 2 Nov

A large house with a covered patio area featuring outdoor seating and a fire pit.

A corner dining area with a wooden table set for four, surrounded by upholstered chairs.

A well-lit room with a large window, a clock, and a fireplace. There are several chairs and a table with a vase.

A sunlit room with large windows, a stone floor, and two rocking chairs.

10. The Whitlock

Lenox

Michael

฿4,843

฿5,410 total

includes taxes & fees

2 Nov - 3 Nov

A hotel patio with outdoor seating and a fire pit.

A modern reception area with a green textured wall, a reception desk, and a coffee machine.

A modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.

A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.

11. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

฿4,301

฿4,804 total

includes taxes & fees

1 Nov - 2 Nov

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

A corner market with a sign reading "the Corner Market" and shelves stocked with various snacks and groceries.

A modern hotel lobby with a seating area, a sofa, and a large window with curtains.

An indoor swimming pool with a diving board, lounge chairs, and a 'No Diving' sign.

12. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

Kelly

฿4,831

฿5,397 total

includes taxes & fees

2 Nov - 3 Nov

A building with a porch and multiple windows, surrounded by purple flowers.

A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

A café with a display case, a frozen food section, and a marketplace sign.

A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

13. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

South Lee

Jared

฿3,935

฿5,053 total

includes taxes & fees

28 Oct - 29 Oct

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

An outdoor seating area with Adirondack chairs and a fire feature.

14. Element by Marriott Lenox Berkshires

Lenox

Kirsty

฿4,809

฿5,372 total

includes taxes & fees

8 Nov - 9 Nov

A two-story house with a brick entrance and a white facade.

A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.

A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.

A neatly arranged bedroom with a bed, bedside table, and a dresser.

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

Stockbridge

Philippe

฿12,845

฿15,539 total

includes taxes & fees

11 Nov - 12 Nov

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

A bed with a white lace bedspread, a tray with cookies and a bottle, and two glasses of red wine.

A dining table set with a vase of flowers, a book, and cutlery.

A loft bedroom with a sloped ceiling, a ceiling fan, a floor lamp, a bed with a patterned bedspread, a chair, and a small table.

16. Brook Farm Inn

Lenox

Carrie

฿6,542

฿7,576 total

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

A hotel room with a sofa, armchair, desk with lamp, television, mini-fridge, and patterned carpet.

A modern living room with a fireplace, two blue armchairs, and decorative vases on the mantel.

17. Quality Inn Lee - Lenox South

Lee

Christine

฿3,116

฿3,481 total

includes taxes & fees

2 Nov - 3 Nov

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

A garden with wooden Adirondack chairs and a stone pathway.

An indoor swimming pool with a high ceiling, multiple windows, and seating areas.

A spacious lobby with a fireplace, seating area, and a bar.

18. Berkshire Mountain Lodge

Pittsfield

Kathleen

฿2,883

฿3,972 total

includes taxes & fees

9 Nov - 10 Nov

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

A reception area with a coffee machine, a water dispenser, and a sign indicating the fitness center.

A reception area with grey upholstered chairs, a wooden reception desk, and a colorful pear painting on the wall.

A hotel room with a patterned carpet, a sofa, a chair, a small table, a lamp, a television on a cabinet, and two framed pictures on the wall.

19. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

฿3,144

฿3,512 total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel lobby with seating areas, tables, and a reception desk.

A kitchenette with a microwave, coffee maker, and coffee cups.

A breakfast area with a counter, coffee machine, and a display of pastries.

A hotel room with two beds, a desk, a TV, and a window with curtains.

20. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Maria Dulce

฿2,791

฿3,118 total

includes taxes & fees

10 Nov - 11 Nov

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Stay near popular West Stockbridge attractions

Ebenezer II Gifts and Antiques

8.0/10 (1 review)

This charming antique shop showcases curated treasures that evoke timeless nostalgia. Spend an hour browsing the eclectic collection and chat with knowledgeable staff about the stories behind unique pieces.

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Hoffman's Pottery

9.4/10 (3 reviews)

Discover vibrant, hand-built ceramic art at Hoffman Pottery, where Elaine's colourful creations exude energy and movement. Browse bowls, vases, and garden sculptures while chatting with the artist about her process.

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Charles H. Baldwin & Sons

This historic shop has crafted pure vanilla extract using traditional methods since 1888. Visit the charming shopfront to discover artisanal extracts and baking ingredients.

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Learn more about West Stockbridge

The historic Turn Park Art Space showcases outdoor sculptures along winding paths overlooking the Housatonic River. Grab breakfast at Six Depot Roastery before browsing the charming shops and galleries along Main Street.

See all hotels in West Stockbridge

A lush green valley with a lake and a house in the distance.

Top West Stockbridge Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"We had a wonderful family stay at Vacation Village in the Berkshires! We traveled with our children and their grandmothers, and it was such a special opportunity to make memories together. Our accommodation felt like two apartments in one, with plenty of space for everyone. We loved the layout and the beautiful views, especially with the fall colors surrounding us. It was lovely to enjoy the scenery right where we were staying. The location was a great base for exploring the Berkshires, and we felt we got excellent value for the price. This trip was very special for our family, and we would love to come back. Highly recommend it for a family getaway!"

Berkshires Untold

10/10 Excellent

"We were only there for one night so we Bailey stayed there for 17 hours, but we found the room very comfortable The bathroom was very upscale and fairly new. The bed was comfortable. The management was very friendly. Great place to stay as a stopover but probably great for a longer stay."

Hotel On North

10/10 Excellent

"Lovely clean spacious hotel with friendly staff!"

The Red Lion Inn

8/10 Good

"I enjoyed my stay, lovely little town. The Inn is beginning to show some signs of wear. A broken tile (baseboard) by the tub. However, staff pleasant and helpful. Excellent restaurants."

Berkshire Mountain Lodge

10/10 Excellent

"Great to have a whole suite not just a room. Even though a little outdated still very nice. Downsides were an absence of food vending machines for when you need a quick snack and don’t want to leave, and hot tub was under renovations which we weren’t made aware of until online check in. Overall very happy."

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"Very clean and new hotel."

Pleasant Valley Motel West Stockbridge

8/10 Good

"Older but well maintained, clean and had basic necessities. Very good for the price. Only problem was trying to adjust heat. Good hot shower. Would come again"

The Yankee Inn

8/10 Good

"Everything at the Yankee Inn was very good with the exception of, wasn’t the most comfortable bed I’ve ever slept in, but everything else was very good"

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"It's a perfect stop on our little Berkshires trip. The Inn had everything we needed and more. The property was beautiful, and the staff was beyond helpful. We will certainly be back."

Frequently asked questions

What's the best place to stay in West Stockbridge?

Shaker Mill Inn is one of the top choices for your stay based on our traveller data. This B&B offers free parking and a library. Pleasant Valley Motel West Stockbridge is another good choice for your stay. See all available top hotels, or vacation rentals in West Stockbridge.

If I need to cancel my hotel reservation in West Stockbridge, will I receive a refund?

Yes! You'll find that most hotel reservations are fully refundable if cancelled prior to the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might still have the option to cancel and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in West Stockbridge.

What is the top LGBTQ-friendly hotel in West Stockbridge?

Shaker Mill Inn is a top LGBTQ-friendly B&B that features free parking and a library. See all available hotels listed as LGBTQ-friendly in West Stockbridge.

What are some hotels with pools in West Stockbridge?

Vacation Village in the Berkshires: Aparthotel, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and free self parking. Berkshire Mountain Lodge and The Yankee Inn are a couple of other choices with an on-site pool. View all hotels with pools in West Stockbridge.

What is staying in West Stockbridge like?

Budget-minded travellers will find good deals in West Stockbridge, and many visitors will definitely appreciate the gardens and restaurants. Tourists can also enjoy so much more including its lake views. In West Stockbridge, there are 33 hotels and other accommodation options to choose from. Find out more about West Stockbridge.

What should I do while I'm visiting West Stockbridge?

Attractions such as Charles H. Baldwin & Sons, Ebenezer II Gifts and Antiques and Hoffman's Pottery are fun for children of all ages. Additionally, you might want to add Stockbridge Bowl to your itinerary. Take a look at what more there is to see and do in Expedia's West Stockbridge guide.

What's the weather like in West Stockbridge?

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 -3°C. The snowiest months in West Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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Book Hotels in West Stockbridge on Expedia.com

Find hotels in West Stockbridge, MA from ฿2,528

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in West Stockbridge

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for West Stockbridge hotels

1. Shaker Mill Inn

2. Pleasant Valley Motel West Stockbridge

3. The Red Lion Inn

4. Courtyard by Marriott Lenox Berkshires

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

6. The Cornell Inn, Lenox & The Berkshires

7. The Yankee Inn

8. Berkshires Untold

9. Hampton Inn & Suites Berkshires-Lenox

10. The Whitlock

11. Hilton Garden Inn Lenox Pittsfield

12. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

13. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

14. Element by Marriott Lenox Berkshires

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

16. Brook Farm Inn

17. Quality Inn Lee - Lenox South

18. Berkshire Mountain Lodge

19. Best Western Plus Berkshire Hills Inn & Suites

20. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Stay near popular West Stockbridge attractions

Ebenezer II Gifts and Antiques

Hoffman's Pottery

Charles H. Baldwin & Sons

Learn more about West Stockbridge

Top West Stockbridge Hotel Reviews

Vacation Village in the Berkshires

Berkshires Untold

Hotel On North

The Red Lion Inn

Berkshire Mountain Lodge

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Pleasant Valley Motel West Stockbridge

The Yankee Inn

The Cornell Inn, Lenox & The Berkshires

Frequently asked questions

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