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 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.

1. The Yankee Inn

Lenox

Basil

Rp1.912.876

Rp2.136.682 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 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.

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

Great Barrington

Rp2.589.579

Rp2.892.560 total

includes taxes & fees

2 Nov - 3 Nov

A snow-covered outdoor area with a patio, seating, and a covered dining area.

A dining area with a glass table, red walls, and framed artwork.

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.

3. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

Rp2.769.267

Rp3.176.349 total

includes taxes & fees

27 Oct - 28 Oct

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 garden with wooden Adirondack chairs and a stone pathway.

4. Berkshire Mountain Lodge

Pittsfield

ulla

Rp1.559.867

Rp2.145.094 total

includes taxes & fees

19 Nov - 20 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 two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

5. Vacation Village in the Berkshires

Williamstown

Adrianne

Rp1.448.325

Rp1.815.536 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

6. Quality Inn Lee - Lenox South

Lee

Lucinda

Rp1.671.962

Rp1.867.581 total

includes taxes & fees

9 Nov - 10 Nov

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

A modern cafe with a counter, seating area, and large windows.

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

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

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

Pittsfield

Ginger

Rp1.714.370

Rp1.914.951 total

includes taxes & fees

17 Nov - 18 Nov

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

A cozy library with bookshelves, a sofa, a coffee table, and a large window with a view of trees.

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".

8. Berkshires Untold

Lenox

Madhavi R

Rp2.346.921

Rp2.621.511 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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.

9. Courtyard by Marriott Lenox Berkshires

Lenox

Vandhana

Rp2.266.758

Rp2.531.969 total

includes taxes & fees

1 Nov - 2 Nov

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

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

Lee

Gustavo

Rp2.024.761

Rp2.261.659 total

includes taxes & fees

15 Nov - 16 Nov

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 Holiday Inn Club Vacations sign for Oak N'Spruce Resort.

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

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

South Lee

Michael

Rp2.109.159

Rp2.708.376 total

includes taxes & fees

28 Oct - 29 Oct

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.

A modern reception area with a green textured wall, a reception desk, and a coffee machine.

12. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

Rp2.307.722

Rp2.577.726 total

includes taxes & fees

1 Nov - 2 Nov

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 library with bookshelves, a television, and two armchairs.

13. Hotel On North

Pittsfield

Devon

Rp2.417.421

Rp2.700.259 total

includes taxes & fees

2 Nov - 3 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 well-lit room with a large window, a clock, and a fireplace. There are several chairs and a table with a vase.

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

14. The Whitlock

Lenox

Michelle

Rp2.526.440

Rp2.822.034 total

includes taxes & fees

18 Nov - 19 Nov

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

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

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

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

15. The Williams Inn

Williamstown

Joshua

Rp3.666.045

Rp4.094.972 total

includes taxes & fees

8 Nov - 9 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 hotel room with a wooden desk, a television, a mirror, and a bathroom visible through an open door.

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

16. Quality Inn Great Barrington

Downtown Great Barrington

Scott Patterson

Rp1.365.180

Rp1.524.905 total

includes taxes & fees

10 Nov - 11 Nov

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

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

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

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

17. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

Rp1.976.661

Rp2.207.930 total

includes taxes & fees

2 Nov - 3 Nov

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

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.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

18. The Red Lion Inn

Stockbridge

Mallory

Rp2.842.606

Rp4.071.715 total

includes taxes & fees

4 Nov - 5 Nov

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 interior with a large window, a wooden table, and bar stools.

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

19. Hotel Downstreet, an Ascend Collection Hotel

North Adams

mary ellen

Rp2.151.083

Rp2.402.760 total

includes taxes & fees

9 Nov - 10 Nov

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Holiday Rentals in The Berkshires

Aparthotel

Berkshire Mountain Lodge

Pittsfield

"Large , clean suite .well equipped kitchen. Comfortable stay! Would definitely return."

Aparthotel

Vacation Village in the Berkshires

Williamstown

"This was a fantastic property to end our New England trip!"

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

"The furnishings- furniture and bed mattress are in need of replacement. The washer/dryer was a great amenity. This is access to an apartment - no services included."

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 kitchen with wooden cabinets, a refrigerator, and a dining area with a round table and chairs.

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 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 spacious living room with a large wooden dining table surrounded by chairs, a sofa, and a coffee table. A kitchen with modern appliances and cabinets is visible in the background.

A kitchen with a wooden countertop, built-in cabinets, a dishwasher, and a stove.

An outdoor seating area with four chairs and a table, surrounded by a gravel patio, a wooden deck, and a grassy lawn.

A bathroom with a sink, mirror, and towel rack.

Ashley Falls Home w/ Fire Pit: Hike & Ski!

Ashley Falls

"We had a great stay! We will definitely be back again."

Apartment

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

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

A single-story house with a sloped roof, a front door, and a small porch area.

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.

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

Top The Berkshires Hotel Reviews

Berkshires Untold

10/10 Excellent

"Had a great time enjoying the outdoor space, the bar, and the "living room" area by the fire. Although our room was on the highway side so could hear traffic, we had a gorgeous view of the mountains and changing foliage. Would go back"

Holiday Inn Club Vacations Oak 'n Spruce Resort

8/10 Good

"The unit was clean and comfortable. Location was nice and quiet. Mini golf and hot tub were fun and appreciated. Unit was dated- cabinets were old. Kitchen was well- stocked. I would suggest having kitchen towels though. Blankets would have been nice ( as the weather was changing.)."