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 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.

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

1. The Yankee Inn

Lenox

Basil

2.748.792 ₫

3.070.402 ₫ 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 hotel lobby with multiple seating areas, including tables and chairs, a large flat-screen TV mounted on the wall, and a patterned carpet.

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.

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

Great Barrington

Kelly

3.722.833 ₫

4.158.404 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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

Pofen

2.082.143 ₫

2.610.052 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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.

4. Berkshires Untold

Lenox

Madhavi R

3.373.983 ₫

3.768.739 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

5. Quality Inn Lee - Lenox South

Lee

2.401.117 ₫

2.682.048 ₫ total

includes taxes & fees

3 Nov - 4 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 hotel lobby with a snow-covered entrance and a sign reading "Lobby".

6. Berkshire Mountain Lodge

Pittsfield

Kathleen

2.221.585 ₫

3.060.473 ₫ total

includes taxes & fees

9 Nov - 10 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.

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

Lee

Gustavo

2.973.861 ₫

3.321.803 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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 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.

8. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

3.257.319 ₫

3.638.425 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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 a counter, seating area, and large windows.

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

Pittsfield

Ginger

2.565.684 ₫

2.865.869 ₫ total

includes taxes & fees

11 Nov - 12 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 dining area with a glass table, red walls, and framed artwork.

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

10. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

3.979.421 ₫

4.564.397 ₫ total

includes taxes & fees

27 Oct - 28 Oct

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 library with bookshelves, a television, and two armchairs.

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

11. Hotel On North

Pittsfield

Lawrence

3.477.481 ₫

3.884.346 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

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

South Lee

Jared

3.034.044 ₫

3.896.024 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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

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

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

A bed with a white pillow and a nightstand with a modern lamp.

13. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

2.841.689 ₫

3.174.166 ₫ total

includes taxes & fees

11 Nov - 12 Nov

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

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.

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

14. The Whitlock

Lenox

Michael

3.734.208 ₫

4.171.110 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

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

15. Quality Inn Great Barrington

Downtown Great Barrington

Joan

2.011.341 ₫

2.246.668 ₫ total

includes taxes & fees

10 Nov - 11 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 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.

16. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

3.316.184 ₫

3.704.127 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A door with a wooden finish and a metallic plate with instructions for an audio-visual door alert for hearing-impaired individuals.

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

A spacious living area with a fireplace, wooden beams, and a large window.

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

17. The Williams Inn

Williamstown

Soleil

5.268.086 ₫

5.884.452 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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

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.

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

18. Howard Johnson by Wyndham Lenox

Lenox

Aleksandr

2.047.364 ₫

2.286.906 ₫ total

includes taxes & fees

19 Oct - 20 Oct

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

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

Great Barrington

Maria Dulce

2.151.028 ₫

2.402.697 ₫ total

includes taxes & fees

12 Nov - 13 Nov

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

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.

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

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

20. Brook Farm Inn

Lenox

Carrie

5.040.921 ₫

5.838.097 ₫ total

includes taxes & fees

13 Nov - 14 Nov

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Holiday Rentals in The Berkshires

Aparthotel

Berkshire Mountain Lodge

Pittsfield

"Friendly hotel staff."

Aparthotel

Vacation Village in the Berkshires

Williamstown

"Beautiful location!"

Aparthotel

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

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

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

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

The Ponds at Foxhollow

Lenox

"Quiet property. Convenient location."

Cottage

A dining area with a wooden table, white chairs, a brick column, a vase with sunflowers, and a basket with bread and tomatoes.

A cozy living room with a sofa, a coffee table, a lamp, and a framed botanical print on the wall.

A kitchen with a wooden island, a brick wall, a vintage stove, and a large wooden door.

An outdoor dining area with a wooden table and white chairs, surrounded by lush greenery and trees.

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

Lee

"What a charming home! The bathrooms and bedrooms were updated beautifully. The downstairs was updated enough while keeping the character."

Apartment

A two-story house with a stone patio, outdoor seating, and a grill.

A dining area with a wooden table and chairs, a bookshelf, and large windows with curtains.

A small, rustic cabin with a stone foundation and a wooden structure covered in climbing vines.

A spacious living room with a blue sofa, a red armchair, and a wooden dining table.

Vacation Rental Home in the Berkshires!

Williamstown

"This little guest house is a gem. Charming, comfortable and with a location that can’t be beat as a base for touring the northern Berkshires and southern Vermont. Everything was in good order, check-in was easy, and the place is well equipped with kitchen essentials. The views are gorgeous. "

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Stay near popular The Berkshires attractions

A forested hillside with a clear path and a small building at the top.

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 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 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 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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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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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

The Yankee Inn

10/10 Excellent

"This is a gem of a small hotel/motel. Super comfortable rooms, updated bathrooms, and well done self serve breakfast included. Also has an indoor pool and an outdoor pool during the season. And a very nice hiking trail off of the back. An excellent change from the Run of the middle courtyard Marriott!"

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

10/10 Excellent

"Very clean and nice options for breakfast. Helpful staff."

Berkshires Untold

8/10 Good

"Enjoyed the view and the aesthetic"

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!"

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."

Quality Inn Great Barrington

10/10 Excellent

"Beds were comfortable, room was clean, train was not often"

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."

More cheap stays in The Berkshires

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

1.609.384 ₫

1.797.682 ₫ total

25 Oct - 26 Oct

includes taxes & fees

5.4/10 (923 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

2.011.341 ₫

2.246.668 ₫ total

10 Nov - 11 Nov

includes taxes & fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

2.047.364 ₫

2.286.906 ₫ total

19 Oct - 20 Oct

includes taxes & fees

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

1055 South Street Pittsfield MA

2.565.684 ₫

2.865.869 ₫ total

11 Nov - 12 Nov

includes taxes & fees

9.2/10 Wonderful! (237 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

2.748.792 ₫

3.070.402 ₫ total

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (1,008 reviews)

The Whitlock

16 Church St Lenox MA

3.734.208 ₫

4.171.110 ₫ total

2 Nov - 3 Nov

includes taxes & fees

Hotels in The Berkshires with star rating

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Find hotels in The Berkshires, MA from 1.732.485 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in The Berkshires

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for The Berkshires hotels

1. The Yankee Inn

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

3. Vacation Village in the Berkshires

4. Berkshires Untold

5. Quality Inn Lee - Lenox South

6. Berkshire Mountain Lodge

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

8. Courtyard by Marriott Lenox Berkshires

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

10. The Cornell Inn, Lenox & The Berkshires

11. Hotel On North

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

13. Hampton Inn & Suites Berkshires-Lenox

14. The Whitlock

15. Quality Inn Great Barrington

16. Hilton Garden Inn Lenox Pittsfield

17. The Williams Inn

18. Howard Johnson by Wyndham Lenox

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

20. Brook Farm Inn

Holiday Rentals in The Berkshires

Berkshire Mountain Lodge

Vacation Village in the Berkshires

The Ponds at Foxhollow

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

Vacation Rental Home in the Berkshires!

Stay near popular The Berkshires attractions

Jiminy Peak Mountain Resort

Tanglewood Music Center

Williams College

Norman Rockwell Museum

Massachusetts Museum of Contemporary Art

Ski Butternut

National Shrine of the Divine Mercy

Lee Premium Outlets

Learn more about The Berkshires

Top The Berkshires Hotel Reviews

The Yankee Inn

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

Berkshires Untold

Vacation Village in the Berkshires

Hotel On North

The Red Lion Inn

Berkshire Mountain Lodge

Quality Inn Great Barrington

The Cornell Inn, Lenox & The Berkshires

More cheap stays in The Berkshires

FairBridge Inn Express

Quality Inn Great Barrington

Howard Johnson by Wyndham Lenox

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

The Yankee Inn

The Whitlock

Hotels in The Berkshires with star rating

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