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 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.

A stone fireplace with a television above it, a kitchen area to the left, and a wooden floor.

1. Shaker Mill Inn

West Stockbridge

Mervin

฿5,753

฿6,311 total

includes taxes & fees

8 Sept - 9 Sept

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

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.

A motel with a row of rooms, a parking lot, and a red car parked in front.

2. Pleasant Valley Motel West Stockbridge

West Stockbridge

Peter

฿2,367

฿2,596 total

includes taxes & fees

1 Sept - 2 Sept

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

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

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

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

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

Great Barrington

Lisa

฿5,281

฿5,899 total

includes taxes & fees

7 Sept - 8 Sept

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

A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

An indoor swimming pool with a 6 feet 18 meters depth, surrounded by chairs and tables, with large windows offering views of trees.

A hotel reception area with a check-in counter, a Holiday Inn Express sign, and a beverage refrigerator.

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

Great Barrington

BJORN

฿3,780

฿4,223 total

includes taxes & fees

7 Sept - 8 Sept

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

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

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

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

5. Courtyard by Marriott Lenox Berkshires

Lenox

Laura

฿5,840

฿6,523 total

includes taxes & fees

7 Sept - 8 Sept

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

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.

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

A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

6. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Jermaine

฿3,773

฿4,215 total

includes taxes & fees

22 Sept - 23 Sept

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

A lakeside dock with kayaks and a covered boat ramp.

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.

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

Lee

Rinat

฿4,191

฿4,682 total

includes taxes & fees

22 Sept - 23 Sept

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

A hotel room with a bed, a desk, a television, a microwave, and a sofa.

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

8. Quality Inn Lee - Lenox South

Lee

Christine

฿3,605

฿4,026 total

includes taxes & fees

22 Sept - 23 Sept

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 cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.

9. The Yankee Inn

Lenox

Karen

฿5,030

฿5,618 total

includes taxes & fees

13 Sept - 14 Sept

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.

10. The Cornell Inn, Lenox & The Berkshires

Lenox

Edward

฿6,496

฿7,451 total

includes taxes & fees

31 Aug - 1 Sept

11. Berkshire Travel Lodge

Austerlitz

Kris

฿2,219

฿2,485 total

includes taxes & fees

2 Sept - 3 Sept

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

A backyard with a swimming pool, lounge chairs, and a hot tub.

A bar with wooden floors and shelves filled with bottles.

A covered porch with wicker furniture and hanging flower baskets.

12. The Red Lion Inn

Stockbridge

Patricia

฿5,216

฿7,471 total

includes taxes & fees

29 Sept - 30 Sept

A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.

A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

13. Howard Johnson by Wyndham Lenox

Lenox

Sheila

฿2,597

฿2,901 total

includes taxes & fees

31 Aug - 1 Sept

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

A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.

A grocery store with shelves stocked with snacks and beverages, a refrigerated display case, and a wall with hexagonal patterns.

14. Hampton Inn & Suites Berkshires-Lenox

Lenox

Nancy

฿4,398

฿4,913 total

includes taxes & fees

13 Sept - 14 Sept

A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

A hotel patio with outdoor seating and a fire pit.

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

A spacious living room with a large sofa, a coffee table, and a fireplace.

15. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

฿5,020

฿5,608 total

includes taxes & fees

13 Sept - 14 Sept

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.

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

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.

16. Berkshires Untold

Lenox

Christine

฿4,633

฿5,175 total

includes taxes & fees

28 Sept - 29 Sept

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.

17. Devonfield Inn B&B

Lee

Richard

฿12,788

฿14,284 total

includes taxes & fees

3 Sept - 4 Sept

A round wooden table with two wine glasses and a green bottle, set against a window with a view of a blue railing and trees.

A motel with multiple rooms, a well-maintained lawn, and a stone pathway.

A hotel reception desk with an orange counter, a computer, a beverage cooler, and framed awards on the wall.

A kitchenette with a refrigerator, coffee maker, toaster, and bread display.

18. Econo Lodge Lee - Great Barrington

Lee

Anna

฿2,278

฿2,545 total

includes taxes & fees

7 Sept - 8 Sept

A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

A multi-story hotel with a brick facade and a flat roof.

A pool area with a glass ceiling, multiple levels, and outdoor seating.

19. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Myrna

฿3,879

฿4,333 total

includes taxes & fees

7 Sept - 8 Sept

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

A living room with a sofa, armchair, coffee table, and a patterned rug.

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

A multi-story building with a symmetrical facade, multiple balconies, and a central tower.

20. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

Claudia

฿3,846

฿4,939 total

includes taxes & fees

7 Sept - 8 Sept

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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

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

"Amazing time. Stayed in the Presidential units. Worth it."

Shaker Mill Inn

10/10 Excellent

"Cute and clean. Did not meet staff"

The Red Lion Inn

10/10 Excellent

"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"

Berkshires Untold

10/10 Excellent

"Chic bar and outdoor space. Nice remodel."

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

10/10 Excellent

"Nice, well-maintained property, everything was very clean. The breakfast nook was not overly crazy crowded, which is really good traveling with young children. The staff even apologized for not having the waffle maker as a new one was being delivered. The hot tub was also a plus!"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"I am not a person who usually writes a review but I loved the place. Room was great. Staff was great. I had never been to an Indian restaurant but everywhere I went people raved about I so we went and it was wonderful. Only a few small issues. The fan in our bathroom room needs attention. Very loud. Something is failing. The wifi was very weak in my room. Kept cutting out. and just one other suggestion. The balcony on the upper level should have privacy screens on the sides. Other wise I would absolutely go back."

St. Charles Hotel

8/10 Good

"Place was clean. Bed was comfortable. Air conditioning was very loud!!"

The Yankee Inn

10/10 Excellent

"One of the quietest rooms we have ever stayed in. The location was very convenient to sites in both Lenox and Stockbridge."

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent

"Fine place to stay in the Lenox area."

More cheap stays in West Stockbridge

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

฿2,041

฿2,280 total

31 Aug - 1 Sept

includes taxes & fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

฿2,597

฿2,901 total

31 Aug - 1 Sept

includes taxes & fees

Quality Inn Great Barrington

372 Main Street Great Barrington MA

฿3,046

฿3,402 total

22 Sept - 23 Sept

includes taxes & fees

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

1055 South Street Pittsfield MA

฿3,879

฿4,333 total

8 Sept - 9 Sept

includes taxes & fees

9.4/10 Exceptional! (176 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

฿5,030

฿5,618 total

13 Sept - 14 Sept

includes taxes & fees

9.2/10 Wonderful! (1,001 reviews)

Pocketbook Hotel and Bath

549 Washington Street Hudson NY

฿7,367

฿9,810 total

31 Aug - 1 Sept

includes taxes & fees

8.6/10 Excellent! (67 reviews)

Frequently asked questions

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

Based on our traveller data, Shaker Mill Inn is one of the top choices for your stay. 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 breakfast and free parking. 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. The Yankee Inn and Berkshire Mountain Lodge 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 34 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 Ebenezer II Gifts and Antiques, Charles H. Baldwin & Sons 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 ฿2,280

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

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

5. Courtyard by Marriott Lenox Berkshires

6. Best Western Plus Berkshire Hills Inn & Suites

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

8. Quality Inn Lee - Lenox South

9. The Yankee Inn

10. The Cornell Inn, Lenox & The Berkshires

11. Berkshire Travel Lodge

12. The Red Lion Inn

13. Howard Johnson by Wyndham Lenox

14. Hampton Inn & Suites Berkshires-Lenox

15. Hilton Garden Inn Lenox Pittsfield

16. Berkshires Untold

17. Devonfield Inn B&B

18. Econo Lodge Lee - Great Barrington

19. Holiday Inn & Suites Pittsfield-Berkshires by IHG

20. Holiday Inn Club Vacations Oak 'n Spruce Resort

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

Holiday Inn Club Vacations Oak 'n Spruce Resort

Shaker Mill Inn

The Red Lion Inn

Berkshires Untold

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

St. Charles Hotel

The Yankee Inn

Best Western Plus Berkshire Hills Inn & Suites

More cheap stays in West Stockbridge

FairBridge Inn Express

Howard Johnson by Wyndham Lenox

Quality Inn Great Barrington

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

The Yankee Inn

Pocketbook Hotel and Bath

Frequently asked questions

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