Stockbridge Holiday Rentals, Massachusetts: Private House Rentals

A nighttime view of a residential area with houses adorned with holiday lights.

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Our top choices for Stockbridge hotels

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 covered porch with wicker furniture and hanging flower baskets.

A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.

1. The Red Lion Inn

Stockbridge

James

4.174.157 ₫

5.950.240 ₫ total

includes taxes & fees

23 Sept - 24 Sept

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

A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.

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

Stockbridge

Philippe

8.558.006 ₫

10.352.703 ₫ total

includes taxes & fees

28 Sept - 29 Sept

A living room with a fireplace, leather sofas, and a dog.

A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.

3. The Inn at Stockbridge

Stockbridge

Jodi

10.719.994 ₫

12.572.756 ₫ total

includes taxes & fees

16 Sept - 17 Sept

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

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

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

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

4. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

Linda

3.032.640 ₫

3.894.221 ₫ total

includes taxes & fees

21 Sept - 22 Sept

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

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.

A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

5. The Yankee Inn

Lenox

Robert

3.006.720 ₫

3.358.507 ₫ total

includes taxes & fees

22 Sept - 23 Sept

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

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

A coffee station with two coffee machines and a variety of coffee pods and cups.

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

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

Great Barrington

Maria Dulce

3.343.680 ₫

3.734.890 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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

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

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.

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

Lee

Susan

3.238.963 ₫

3.617.922 ₫ total

includes taxes & fees

21 Sept - 22 Sept

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

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

2.776.032 ₫

3.100.828 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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.

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

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

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

Great Barrington

Bruce

5.045.328 ₫

5.635.631 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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

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

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

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

10. Berkshire Mountain Lodge

Pittsfield

Robert

2.063.214 ₫

2.883.664 ₫ total

includes taxes & fees

1 Oct - 2 Oct

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

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

A cozy lounge area with plush seating, a fireplace, and large windows offering a view of the outdoors.

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

11. The Whitlock

Lenox

Maeve

3.723.408 ₫

4.159.047 ₫ total

includes taxes & fees

16 Sept - 17 Sept

A hotel room with two beds, a bedside table with a lamp, and a window with a view of greenery.

A motel with a parking lot and several cars parked.

A row of motel rooms with red doors, a covered walkway, and a view of mountains in the background.

A row of white plastic chairs on a covered outdoor area with a white building in the background.

12. Monument Mountain Motel

Great Barrington

Analisia

2.216.160 ₫

2.475.360 ₫ total

includes taxes & fees

16 Sept - 17 Sept

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

A bar area with a central island, red bar stools, and shelves stocked with bottles and glasses.

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

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

13. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

3.791.578 ₫

4.235.328 ₫ total

includes taxes & fees

20 Sept - 21 Sept

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

A spacious living room with large windows, a fireplace, and a variety of seating options.

14. Vacation Village in the Berkshires

Williamstown

Sarah

2.466.114 ₫

3.038.991 ₫ total

includes taxes & fees

21 Sept - 22 Sept

A building entrance with a large planter with purple flowers and a small tree.

A library with bookshelves, a television, and two armchairs.

A lobby with a red sofa, two armchairs, a wooden table with a vase, brick walls, and an ornate ceiling.

A spacious room with a large window, a brick wall, a sofa set, and a patterned carpet.

15. Hotel On North

Pittsfield

Drew

3.479.760 ₫

3.886.891 ₫ total

includes taxes & fees

16 Sept - 17 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.

16. Hampton Inn & Suites Berkshires-Lenox

Lenox

Nancy

3.478.982 ₫

3.886.023 ₫ total

includes taxes & fees

23 Sept - 24 Sept

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

An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.

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

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

17. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

5.079.802 ₫

5.674.138 ₫ total

includes taxes & fees

20 Sept - 21 Sept

A spacious indoor area with a reception desk, multiple seating arrangements, and a view of the outdoors through large windows.

A hotel reception area with framed artwork, a coffee machine, and a sign indicating 'Quality by Choice Hotels'.

A Quality Inn sign, a brick building, and a parking lot with cars.

A hotel room with a bathroom, a bed, a desk, and a nightstand.

18. Quality Inn Great Barrington

Great Barrington

Kimberly

2.684.016 ₫

2.997.907 ₫ total

includes taxes & fees

17 Sept - 18 Sept

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

A cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.

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.

19. Brook Farm Inn

Lenox

Carrie

6.520.176 ₫

7.490.362 ₫ total

includes taxes & fees

20 Sept - 21 Sept

A large house with a balcony and a grassy yard.

A two-story building with a gabled roof and a chimney.

A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.

A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.

20. The Little Lion

Great Barrington

Anne

2.916.000 ₫

3.257.172 ₫ total

includes taxes & fees

16 Sept - 17 Sept

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Stay near popular Stockbridge attractions

Norman Rockwell Museum

9.4/10 (347 reviews)

This gallery houses the world's largest collection of Norman Rockwell's iconic American illustrations. Explore his relocated studio on the scenic Berkshire estate for insight into his creative process.

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National Shrine of the Divine Mercy

9.0/10 (83 reviews)

This serene sanctuary in the Berkshire Mountains is a centre for Divine Mercy devotion inspired by Saint Faustina. Visitors can join the daily 3:00 PM Chaplet or walk contemplative trails.

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Naumkeag Museum

9.4/10 (10 reviews)

This Gilded Age estate features a 44-room "cottage" with original Choate family furnishings. Explore the iconic Blue Steps and designed gardens while enjoying panoramic Berkshire Mountain views.

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Berkshire Botanical Garden

9.4/10 (14 reviews)

Explore 15 acres of meticulously designed "garden rooms" showcasing over 3,000 plant species native to the Berkshires. The garden's seasonal exhibitions offer an educational journey through horticulture and conservation.

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Stockbridge Bowl

This 372-acre Berkshire lake offers serene boating, fishing, and swimming against a backdrop of rolling hills. In winter, Stockbridge Bowl transforms into a magical venue for ice-skating and ice-fishing.

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Berkshire Theatre Festival

8.8/10 (3 reviews)

The historic Berkshire Theatre Festival presents classic and contemporary plays in intimate venues. Attend a summer evening performance for an immersive cultural experience in picturesque Stockbridge.

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Frelinghuysen Morris House and Studio

8.2/10 (10 reviews)

Step inside the Bauhaus-inspired home of pioneering abstract artists Morris and Frelinghuysen, surrounded by masterworks from Picasso and Léger. Wander the estate's woodland trails after admiring their art collection.

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Schantz Galleries

7.2/10 (5 reviews)

This renowned gallery showcased museum-quality glass sculptures from masters like Chihuly and Tagliapietra. Though permanently closed since 2023, its legacy lives on in the contemporary glass art movement.

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Learn more about Stockbridge

Norman Rockwell's Museum showcases the artist's iconic paintings of small-town American life in his former studio. Stroll down Main Street's historic district before hiking Monument Mountain for views that inspired Nathaniel Hawthorne's literary works.

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A calm lake reflecting a forest with autumn foliage.

Top Stockbridge Hotel Reviews

Quality Inn Great Barrington

10/10 Excellent

"Beds were comfortable but the pillows not so great but clean and quiet."

The Yankee Inn

10/10 Excellent

"We were here for a good night’s rest on a cross country roadtrip. This place had very good Expedia reviews and I agree. Very clean, decent breakfast, plenty of hot water, a toilet that flushed properly. Did not use amenities. Sleep, shower, quiet time to read some, eat and on down the highway. Would gladly stay here again the next time thru the Berkshires."

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

10/10 Excellent

"Pristine and new. Staff was friendly and the breakfast was delicious."

Hotel On North

10/10 Excellent

"Great location, clean room!"

The Whitlock

10/10 Excellent

"Front desk staff amazing. Very quaint and well maintained building. Room large and free standing tub wonderful. Great location. Good bargin as well."

The Red Lion Inn

8/10 Good

"We stopped at the red lion Inn on our travels back home from Maine. Our room was a block away from the main building and in an old house. It was very clean and comfortable. The location in town is nice."

Quality Inn Lee - Lenox South

8/10 Good

"Therooms were loud on the lower level."

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"The temp was 67 degrees in our unit. I called the front desk and they sent someone immediately however who couldn’t get the heat to turn on. The thermostat was not set to turn on until later in the month. The owner must likely to blame for a lack of heat."

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