The Berkshires Holiday Rentals, Massachusetts: Private House Rentals

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Go beyond your typical stay in The Berkshires

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

1. The Yankee Inn

Lenox

Karen

3.025.280 ₫

3.379.238 ₫ total

includes taxes & fees

22 Sept - 23 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.

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

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

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

Great Barrington

Bruce

4.929.120 ₫

5.505.828 ₫ total

includes taxes & fees

8 Sept - 9 Sept

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

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

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

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

3. Berkshire Mountain Lodge

Pittsfield

Robert

2.075.950 ₫

2.901.463 ₫ total

includes taxes & fees

1 Oct - 2 Oct

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

4. Vacation Village in the Berkshires

Williamstown

Alex

2.481.336 ₫

3.057.750 ₫ total

includes taxes & fees

15 Sept - 16 Sept

An indoor swimming pool with clear water, tiled floors, and a blue wall.

A snack bar with shelves of snacks and a refrigerated display.

A modern cafe with seating areas, a coffee station, and large windows offering a view of greenery.

A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

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

Pittsfield

Steve

3.312.160 ₫

3.699.709 ₫ 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.

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.

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 sofa, a coffee table, and a large window with a view of trees.

6. Berkshires Untold

Lenox

David

3.433.484 ₫

3.835.202 ₫ total

includes taxes & fees

9 Sept - 10 Sept

An outdoor seating area with Adirondack chairs and potted plants.

A reception area with a bulletin board, a 'no smoking' sign, a clock, and a 'STOP' sign.

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

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

7. Cozy Corner Motel

Williamstown

Janis

2.300.256 ₫

2.703.714 ₫ total

includes taxes & fees

9 Sept - 10 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 hotel room with two beds, a nightstand with a lamp, a television, and framed artwork on the wall.

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

8. The Villager Motel

Williamstown

Rebecca

2.321.120 ₫

2.592.613 ₫ total

includes taxes & fees

8 Sept - 9 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 hotel room with a bathroom, a bed, a desk, and a nightstand.

A hotel room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.

9. Quality Inn Great Barrington

Great Barrington

Sisile

2.700.584 ₫

3.016.413 ₫ total

includes taxes & fees

9 Sept - 10 Sept

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

A restaurant with a large open dining area, wooden tables and chairs, and a brick wall with a colorful mural.

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

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

10. Hotel On North

Pittsfield

Drew

3.501.240 ₫

3.910.885 ₫ total

includes taxes & fees

8 Sept - 9 Sept

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

A garden with a wooden pergola, potted plants, and a lawn with chairs.

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

A swimming pool with lounge chairs and a fence.

11. Maple Terrace Motel

Williamstown

Annette

3.260.000 ₫

3.641.550 ₫ total

includes taxes & fees

9 Sept - 10 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 white plastic chairs on a covered outdoor area with a white building in the background.

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

12. Monument Mountain Motel

Great Barrington

Jay

2.229.840 ₫

2.490.640 ₫ total

includes taxes & fees

8 Sept - 9 Sept

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

A lakeside lodge with a dock, fishing rods, and outdoor seating.

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.

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

Lee

Susan

3.396.659 ₫

3.794.069 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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

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

A sauna room with wooden walls, a bench, a heater, and a door leading to an outdoor area.

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

14. Blue Vista Motor Lodge

North Adams

Frederic

5.582.650 ₫

5.900.861 ₫ total

includes taxes & fees

8 Sept - 9 Sept

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

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

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

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

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

Great Barrington

BJORN

3.442.560 ₫

3.845.235 ₫ total

includes taxes & fees

15 Sept - 16 Sept

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

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

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 hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.

16. Howard Johnson by Wyndham Lenox

Lenox

irene

2.060.320 ₫

2.301.378 ₫ total

includes taxes & fees

8 Sept - 9 Sept

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

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.

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

17. Hotel Downstreet, an Ascend Collection Hotel

North Adams

Basil

3.734.656 ₫

4.171.611 ₫ total

includes taxes & fees

27 Sept - 28 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 Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

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.

18. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Prasanna

2.344.931 ₫

2.619.287 ₫ total

includes taxes & fees

9 Sept - 10 Sept

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.

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

19. Quality Inn Lee - Lenox South

Lee

Christine

2.637.992 ₫

2.946.637 ₫ total

includes taxes & fees

27 Sept - 28 Sept

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

20. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

Linda

2.675.808 ₫

3.498.893 ₫ total

includes taxes & fees

14 Sept - 15 Sept

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Holiday Rentals in The Berkshires

Aparthotel

Berkshire Mountain Lodge

Pittsfield

"Clean & comfortable stay"

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

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

A stone bench by a calm lake with a stone wall and grass in the foreground.

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

The Ponds at Foxhollow

Lenox

"Great place"

Cottage

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

A rustic wooden interior with a counter displaying various items, a sign for 'MERLOT', and a view of the outdoors.

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

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 wooden deck with outdoor seating and a view of a forest.

A wooden cabin with a balcony, surrounded by a stone wall and a forest.

A cozy dining area with a round table, chairs, and a hanging light fixture.

A cozy attic room with a sloped ceiling, wooden beams, a ceiling fan, and a large window with a view of the outdoors.

A-frame Cabin w/ Furnished Deck in Becket!

Becket

"This cabin has absolutely everything you can think of!! Shampoo, conditioner, pots and pans, cutlery, towels, bug spray, firewood, fans, AC, even a car charger!! I was a little worried because I didn’t connect with the property manager but I had received all the check in information I needed. Absolutely no worries needed! Check in and check out was totally seamless."

Cottage

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

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.

A wooden-paneled bedroom with a bed, two wall-mounted lamps, and large windows.

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 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 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 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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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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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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Ski Butternut

9.0/10 (134 reviews)

Ski Butternut offers 22 diverse trails across 110 acres of terrain suitable for all skill levels. Morning visits reward skiers with freshly groomed slopes and the satisfaction of first tracks.

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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.

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

Top The Berkshires Hotel Reviews

Hotel On North

10/10 Excellent

"This is a hidden gem in the Berkshires. The hotel is clean, rooms are gorgeous and the staff was really helpful."

The Whitlock

10/10 Excellent

"Best hotel we have ever stayed in"

Jiminy Peak Mountain Resort

10/10 Excellent

"The room was spotless and very comfortable. The bed was super comfortable and the shower was nice. The whole property was well kept and the country store is worth a look. We would definitely stay there again!"