The Berkshires Holiday Rentals, Massachusetts: Private House Rentals

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Our top choices for The Berkshires hotels

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

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.

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.

1. The Yankee Inn

Lenox

Karen

3.963.856 ₫

4.427.523 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

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

A garden with wooden Adirondack chairs and a stone pathway.

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

2. Berkshire Mountain Lodge

Pittsfield

Robert

2.466.879 ₫

3.338.086 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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

An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

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

3. Vacation Village in the Berkshires

Williamstown

Alex

2.265.329 ₫

2.816.448 ₫ total

includes taxes & fees

31 Aug - 1 Sept

A kitchen with a countertop, a refrigerator, and a window.

A motel named 'The Villager Motel' with a 'VACANCY' sign, a picnic table, and a red planter on the lawn.

A park with picnic tables, a playground, and a large coniferous tree.

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

4. The Villager Motel

Williamstown

Rebecca

2.320.942 ₫

2.592.414 ₫ total

includes taxes & fees

1 Sept - 2 Sept

An outdoor seating area with Adirondack chairs and potted plants.

A building with a double door labeled "WELCOME" and "OFFICE," a "PARKING ONLY" sign, and flower baskets on either side of the entrance.

A sign with the word "CLARM" on a grassy field with a road and trees in the background.

A hotel room with a large bed, two bedside lamps, a nightstand, a framed picture on the wall, and a window with curtains.

5. Cozy Corner Motel

Williamstown

Janis

2.300.080 ₫

2.703.507 ₫ total

includes taxes & fees

10 Sept - 11 Sept

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

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

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.

6. Berkshires Untold

Lenox

Christine

3.649.146 ₫

4.076.096 ₫ total

includes taxes & fees

28 Sept - 29 Sept

A garden with a swing set, a blue chair, and a flower bed.

A breakfast buffet setup with cereal, milk, juice, and pastries.

A swimming pool with lounge chairs and a fence.

A house with a porch, snow-covered ground, and a Christmas tree with lights.

7. Maple Terrace Motel

Williamstown

Annette

3.259.750 ₫

3.641.271 ₫ total

includes taxes & fees

14 Sept - 15 Sept

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

A hotel room with a wooden dresser, a television, a microwave, and a mirror.

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

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

8. Monument Mountain Motel

Great Barrington

John

2.229.669 ₫

2.490.449 ₫ 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.

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

A hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

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

Great Barrington

Lisa

4.189.431 ₫

4.679.595 ₫ total

includes taxes & fees

7 Sept - 8 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 lakeside dock with kayaks and a covered boat ramp.

A lodge with a large building and a dock by a lake, surrounded by forest.

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

Lee

James

3.324.945 ₫

3.713.962 ₫ total

includes taxes & fees

21 Sept - 22 Sept

A fire pit with four Adirondack chairs arranged around it, overlooking a snowy landscape with distant mountains.

A large, single-story building with a red and white exterior, surrounded by green fields and a winding road.

A hotel room with two beds, a desk, a chair, a lamp, and a view of the mountains.

A modern building with a flat roof and large windows, surrounded by a pond and trees with autumn foliage.

11. Blue Vista Motor Lodge

North Adams

Frederic

5.582.222 ₫

5.900.409 ₫ total

includes taxes & fees

31 Aug - 1 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 modern kitchen with a coffee machine, a refrigerator, and a dining area with chairs and tables.

12. Quality Inn Lee - Lenox South

Lee

Christine

2.859.453 ₫

3.194.009 ₫ total

includes taxes & fees

20 Sept - 21 Sept

A hotel room with a bed, a sofa, a TV, and a bathroom visible through an open door.

A modern hotel building with the name "Hotel Downtown" on the facade.

A reception area with a large landscape painting, a dark reception desk, and a potted plant.

A modern cafe with a wooden accent wall, a coffee machine, and black chairs.

13. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Peter

3.963.856 ₫

4.427.626 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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

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.

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

14. Hotel On North

Pittsfield

Drew

4.667.962 ₫

5.214.114 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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.

An indoor swimming pool with clear water, a lifeguard station, and a sign indicating no lifeguard on duty.

15. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

Claudia

3.051.126 ₫

3.917.959 ₫ 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.

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

Great Barrington

BJORN

2.999.545 ₫

3.350.622 ₫ total

includes taxes & fees

7 Sept - 8 Sept

A patio area with wooden chairs and tables, surrounded by dense greenery and trees.

A hotel room with two blue upholstered chairs, a wooden table with a lamp, a TV mounted on the wall, and a wooden dresser with drawers.

A hay bale display with pumpkins and scarecrows.

A white two-story building with a porch, labeled as a motel.

17. Willows Motel Williamstown

Williamstown

Richard

2.204.895 ₫

2.462.806 ₫ total

includes taxes & fees

30 Aug - 31 Aug

A patio area with outdoor furniture, a fire pit, and potted plants.

A poolside area with lounge chairs, umbrellas, and a swimming pool.

A bar area with stools, a counter displaying fruits and beverages, and a sign reading "Springs".

A cozy living room with a stone fireplace, comfortable seating, and a television.

18. The Springs Motel

New Ashford

Elizabeth

3.198.428 ₫

3.508.676 ₫ total

includes taxes & fees

31 Aug - 1 Sept

A large, multi-story building with a prominent stone facade and a metal roof, surrounded by landscaped gardens and a pedestrian bridge.

A spacious interior with a wooden staircase, a seating area with patterned cushions, and large windows allowing natural light.

A bar area with wooden beams, red chairs, and a long wooden table.

An outdoor seating area with stone fire pit, chairs, and a red building in the background.

19. The Williams Inn

Williamstown

John

6.849.387 ₫

7.650.765 ₫ total

includes taxes & fees

13 Sept - 14 Sept

A calm lake at dusk with a wooden dock and two chairs facing the water.

A lakeside dock with chairs and a table, surrounded by greenery and a clear sky.

A room with two beds, a round mirror, a red box, and a hanging light fixture.

20. Berkshire Lake Lodge

Lee

mike

3.911.700 ₫

4.369.369 ₫ total

includes taxes & fees

31 Aug - 1 Sept

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Holiday Rentals in The Berkshires

Aparthotel

Vacation Village in the Berkshires

Williamstown

"All the amenities offered are an excellent plus. Good rates for rooms. Good place to stay at, lots to do even around the area"

Aparthotel

Berkshire Mountain Lodge

Pittsfield

"A nice place to stay in the Berkshires."

Aparthotel

A large, multi-story house with a reflective pond in front, surrounded by stone walls and trees.

A serene pond with a stone bridge, surrounded by lush greenery and a house in the background.

A spacious loft-style living room with high ceilings, large windows, and a fireplace.

The Ponds at Foxhollow

Lenox

"Great place"

Residence

A wooden cabin with a covered deck, a fire pit, and string lights.

A cozy room with a wood-burning stove, two wooden chairs, a small table, and a window overlooking a snowy landscape.

A wooden cabin with a porch and a small deck, surrounded by trees in a forest.

A swimming pool with a wooden deck, lounge chairs, and umbrellas.

Huttopia Berkshires

Williamstown

"Healthy food too!"

Cottage

A spacious living room with a fireplace, leather sofas, a coffee table, and a dining area with a table and chairs.

A spacious living area with a stone fireplace, wooden ceiling, and large windows.

A sign for Balderdash Cellars with a wooden fence, a tree, and a parking lot in the background.

A modern kitchen with light grey cabinets, stainless steel appliances, and a large window providing a view of greenery.

3 Acres, Mtn Views, Hot Tub, Steps to Winery

Richmond

"This home is exceptional in all respects --beautifully situated on lovely property, well located in southern Berkshires. Newly remodeled. Great outdoor space. Fabulous kitchen with new appliances, extremely well-outfitted. Host easily accessible. Exceeded all expectations. Would definitely return if plans allow."

Cottage

A cozy cabin interior with a stone fireplace, wooden walls, and large windows offering forest views.

A wooden cabin kitchen with a central island, wooden cabinets, a microwave, a refrigerator, and a built-in oven.

A wooden cabin interior with a kitchen area, dining space, and a covered seating area.

A wooden cabin with a staircase leading up to a deck, surrounded by a forest.

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Sandisfield

"We had an amazing experience! Such a beautiful home and amazing host! We loved it! Definitely staying here again. Highly recommend! Thank you! "

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Stay near popular The Berkshires attractions

A wooden pergola structure with a pathway covered in fallen leaves, surrounded by trees and grass.

Tanglewood Music Center

9.6/10 (457 reviews)

Tanglewood enchants as the summer home of the Boston Symphony Orchestra, set in the picturesque Berkshire Hills. Enjoy world-class performances while picnicking on the expansive lawns as the sun sets over the mountains.

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A hillside with autumn-colored trees and five wind turbines against a blue sky with clouds.

Jiminy Peak Mountain Resort

8.8/10 (311 reviews)

Southern New England's largest ski resort transforms into a summer playground with thrilling attractions. Glide down 45 winter trails or ride the Mountain Coaster through Berkshire Mountain scenery.

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A building with 'MASS MoCA' written on it, surrounded by greenery and hills.

Massachusetts Museum of Contemporary Art

9.4/10 (246 reviews)

This converted factory houses one of America's largest contemporary art museums. Wander through MASS MoCA's vast industrial galleries to experience thought-provoking works that transcend artistic boundaries.

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A historic building with ivy-covered brick walls, a large lawn, and a clear blue sky.

Williams College

9.4/10 (534 reviews)

Williams College offers a prestigious liberal arts education amid the scenic Berkshire Mountains. Visitors can explore the renowned Williams College Museum of Art and attend public lectures in this intellectual haven.

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A calm river surrounded by autumn foliage.

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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A tall, conical tower with a spherical top, surrounded by a grassy field and a stone staircase leading up to it.

Mount Greylock

9.4/10 (180 reviews)

Massachusetts' highest peak rewards hikers with panoramic views stretching 90 miles on clear days. Explore the Appalachian Trail segment or stay overnight at the historic Bascom Lodge for a summit sunrise experience.

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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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Lee Premium Outlets

8.2/10 (265 reviews)

You can do some window-shopping at Lee Premium Outlets during your visit to Lee. Amble around the area's gardens or attend a sporting event.

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Learn more about The Berkshires

Tucked in western Massachusetts, this region blends culture and nature with world-class museums and lush hiking trails. Catch a summer concert at Tanglewood, explore Norman Rockwell's art in Stockbridge, or ski the slopes at Jiminy Peak in nearby Hancock.

See all hotels in The Berkshires

A large white building with multiple chimneys, surrounded by lush gardens with various flowers.

Top The Berkshires Hotel Reviews

Berkshire Mountain Lodge

8/10 Good

"the good….full kitchen, living room, king bedroom, clean bathroom, VERY reasonable nightly rate, especially for central berkshire county in the summer. there is no daily room cleaning, but extra towels, etc are always available from the front desk… the less than good…we’ve stayed here now u time in the past 18 months, but the last couple of stays the rooms have been a little musty and damp, despite (or because of?) the a/c being on constantly. ya gotta hold the handle down on the toilet to get a complete flush. no food service, but the is a stop&shop literally across the street… i would still recommend BML for the room rate and location alone…"

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent

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

Hotel On North

10/10 Excellent

"One of my favorite hotels in America - for real!"

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!"

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"Room was"

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 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."

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent

"Nice place"

More cheap stays in The Berkshires

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

1.619.444 ₫

1.808.919 ₫ total

31 Aug - 1 Sept

includes taxes & fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

2.060.162 ₫

2.301.200 ₫ total

31 Aug - 1 Sept

includes taxes & fees

Quality Inn Great Barrington

372 Main Street Great Barrington MA

2.416.127 ₫

2.698.813 ₫ total

20 Sept - 21 Sept

includes taxes & fees

Best Western Plus Berkshire Hills Inn & Suites

1350 W Housatonic St Pittsfield MA

2.993.494 ₫

3.343.734 ₫ total

20 Sept - 21 Sept

includes taxes & fees

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

1055 South Street Pittsfield MA

3.077.204 ₫

3.437.341 ₫ total

8 Sept - 9 Sept

includes taxes & fees

9.4/10 Exceptional! (176 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

3.963.856 ₫

4.427.523 ₫ total

27 Sept - 28 Sept

includes taxes & fees

9.2/10 Wonderful! (1,001 reviews)

Hotels in The Berkshires with star rating

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Find hotels in The Berkshires, MA from 1.808.919 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in The Berkshires

Check prices for these dates

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Our top choices for The Berkshires hotels

1. The Yankee Inn

2. Berkshire Mountain Lodge

3. Vacation Village in the Berkshires

4. The Villager Motel

5. Cozy Corner Motel

6. Berkshires Untold

7. Maple Terrace Motel

8. Monument Mountain Motel

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

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

11. Blue Vista Motor Lodge

12. Quality Inn Lee - Lenox South

13. Hotel Downstreet, an Ascend Collection Hotel

14. Hotel On North

15. Holiday Inn Club Vacations Oak 'n Spruce Resort

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

17. Willows Motel Williamstown

18. The Springs Motel

19. The Williams Inn

20. Berkshire Lake Lodge

Holiday Rentals in The Berkshires

Vacation Village in the Berkshires

Berkshire Mountain Lodge

The Ponds at Foxhollow

Huttopia Berkshires

3 Acres, Mtn Views, Hot Tub, Steps to Winery

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Stay near popular The Berkshires attractions

Tanglewood Music Center

Jiminy Peak Mountain Resort

Massachusetts Museum of Contemporary Art

Williams College

Norman Rockwell Museum

Mount Greylock

National Shrine of the Divine Mercy

Lee Premium Outlets

Learn more about The Berkshires

Top The Berkshires Hotel Reviews

Berkshire Mountain Lodge

Holiday Inn Club Vacations Oak 'n Spruce Resort

Hotel On North

The Red Lion Inn

The Cornell Inn, Lenox & The Berkshires

Berkshires Untold

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

The Yankee Inn

Hotel Downstreet, an Ascend Collection Hotel

More cheap stays in The Berkshires

FairBridge Inn Express

Howard Johnson by Wyndham Lenox

Quality Inn Great Barrington

Best Western Plus Berkshire Hills Inn & Suites

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

The Yankee Inn

Hotels in The Berkshires with star rating

Explore a world of travel with Expedia

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