Lee Holiday Rentals, Massachusetts: Private House Rentals

A street lined with historic buildings, including a Morgan House restaurant.

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Our top choices for Lee hotels

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.

1. Quality Inn Lee - Lenox South

Lee

Christine

2.397.041 ₫

2.677.494 ₫ 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 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 dock with kayaks and a covered boat ramp.

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

Lee

Bob

3.056.777 ₫

3.414.420 ₫ total

includes taxes & fees

10 Nov - 11 Nov

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 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.

3. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

3.249.782 ₫

3.630.006 ₫ 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 living room with a sofa, armchair, coffee table, and a patterned rug.

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

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

South Lee

Jared

3.027.024 ₫

3.886.983 ₫ total

includes taxes & fees

14 Oct - 15 Oct

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

5. The Yankee Inn

Lenox

Basil

2.742.432 ₫

3.063.296 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

A bar with wooden floors and shelves filled with bottles.

A covered porch with wicker furniture and hanging flower baskets.

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

6. The Red Lion Inn

Stockbridge

Stephan

4.075.357 ₫

5.837.494 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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

A snow-covered outdoor area with a small bridge over a stream, surrounded by trees and illuminated by string lights.

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.

7. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

3.970.214 ₫

4.553.835 ₫ total

includes taxes & fees

27 Oct - 28 Oct

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

8. The Whitlock

Lenox

Michael

3.803.184 ₫

4.248.157 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A two-story building with a sign reading "Chambéry Inn".

A large, historic building labeled "Chambéry Inn" with a vintage turquoise truck parked in front.

A hotel room with a large bed, a TV mounted above a fireplace, a desk, and a seating area with chairs.

A hotel room with a TV displaying 'World of Dance', a fireplace, a bed, and a seating area with a remote control.

9. Chambery Inn

Lee

Alexandra

6.985.181 ₫

7.802.477 ₫ total

includes taxes & fees

10 Nov - 11 Nov

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.

10. Berkshires Untold

Lenox

Madhavi R

3.368.254 ₫

3.762.339 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A large, two-story house with a well-maintained lawn and a fence.

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

A bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.

A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.

11. Devonfield Inn B&B

Lee

Sebastien

9.546.768 ₫

10.663.662 ₫ total

includes taxes & fees

5 Nov - 6 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 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.

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

Great Barrington

Kelly

3.716.513 ₫

4.151.345 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.

A swimming pool with a fenced area, lounge chairs, and a warning sign.

A standard rectangular bathtub with a single faucet, tiled walls, and a geometric patterned floor.

A hotel room with two beds, a chair, and a bedside table with a phone.

13. Sunset Inn

Lee

Lauren

2.305.195 ₫

2.574.902 ₫ total

includes taxes & fees

26 Oct - 27 Oct

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

A hotel patio with outdoor seating and a fire pit.

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

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

14. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

3.308.511 ₫

3.695.556 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

A conference room with multiple tables and chairs, a flat-screen TV mounted on the wall, and a carpeted floor.

A room with a blue armchair, an orange armchair, a round table, a floor lamp, and a wardrobe.

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

15. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

2.946.821 ₫

3.291.599 ₫ total

includes taxes & fees

7 Nov - 8 Nov

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

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

16. Berkshire Mountain Lodge

Pittsfield

marilyn

2.217.814 ₫

3.055.278 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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

A dining table set with a vase of flowers, a book, and cutlery.

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

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.

17. Brook Farm Inn

Lenox

Carrie

5.032.363 ₫

5.828.186 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

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

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

Pittsfield

Ginger

2.561.328 ₫

2.861.003 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A hotel room with a bed, a desk, and two wall-mounted lamps.

A motel with a central entrance, a flag, and a parking area with several cars.

A hotel room with a bed, two bedside tables, a desk, two chairs, and a large window with a view of greenery.

A hotel reception desk with an orange counter, a computer, a beverage cooler, and framed awards on the wall.

19. Econo Lodge Lee - Great Barrington

Lee

Anna

1.693.322 ₫

1.891.442 ₫ total

includes taxes & fees

6 Nov - 7 Nov

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.

20. The Inn at Stockbridge

Stockbridge

Jodi

9.753.227 ₫

11.439.305 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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Stay near popular Lee attractions

Goose Pond Reservation

8.4/10 (15 reviews)

This Berkshire woodland preserve features a 2.2-mile loop trail with ridge views 1,753 feet above sea level. Hikers enjoy dense forests and protected shoreline vistas while respecting the natural habitat.

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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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Berkshire Scenic Railway Museum

8.2/10 (13 reviews)

Step back in time at this 1903 New Haven Depot showcasing Berkshire's railway heritage. Enjoy guided tours and vintage train rides aboard the "Lenox Jitney" during summer Saturdays.

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Wood's Pond

8.0/10 (13 reviews)

Wood's Pond offers a peaceful retreat where 181 bird species soar above calm Berkshire waters. Explore its network of trails through lush forests or cast a line from the tranquil shoreline.

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Tyringham Cobble

8.0/10 (15 reviews)

This geological wonder offers panoramic views of the Tyringham Valley. Hike through wildflower meadows to discover Rabbit Rock, a distinctive sandstone formation that crowns this peaceful Berkshire retreat.

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McLennan Reservation

6.8/10 (6 reviews)

Traverse the pristine 594-acre McLennan Reservation through forests and past historic stone walls. The 1.5-mile loop trail leads to tranquil Hale Pond, nestled between mountains in the unspoiled Berkshires.

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Lee Library

8.2/10 (23 reviews)

The only Carnegie library left in the Berkshires, Lee Library features classical revival architecture in local marble. Browse its collection while enjoying polished birch woodwork and cosy reading areas.

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Ashintully Gardens

9.4/10 (6 reviews)

Wander through elegant gardens with classical statuary and footbridges over a babbling brook. A woodland trail leads to the ruins of the "Marble Palace" with panoramic valley views.

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Learn more about Lee

Nestled in the Berkshires, this charming town invites you to explore its quaint streets and local shops. Bargain hunters flock to Lee Premium Outlets, while nature lovers find solace hiking the scenic trails of Goose Pond Reservation.

See all hotels in Lee

A historic street with brick buildings, storefronts, and parked cars.

Top Lee Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"The hotel is an older building but is clean and well maintained. The view of the lake was nice. Breakfast was just ok. Bed was very comfortable. Michelle was very helpful. My only disappointment was that the kayaks were not complimentary. It cost $30 an hour for each kayak."

Berkshire Lake Lodge

10/10 Excellent

"Comfortable property, beautiful view."

Quality Inn Lee - Lenox South

10/10 Excellent

"My wife and I were touring the Berkshires near the end of a long road trip. We’re so glad we chose this Quality Inn in Lee for our stay! Staff in the afternoon/evening, at breakfast, and at the morning desk were all professional, friendly, and helpful. Our room was very clean and comfortable, and the amenities worked well. The continental breakfast included not only stations for waffles and toast, it also included tasty Jimmy Dean breakfast sandwiches to microwave. Coffee and tea and hot chocolate were available 24/7. Art related to nature and the Berkshires was on the walls. A highly recommended property!"

Sunset Inn

8/10 Good

"We were in town for a show at Tanglewood in Lenox. Concert had been rescheduled with little notice; so it put us in a tight spot with no time to add time to being in the Berkshires. I just looked for an inexpensive overnight to just sleep before heading back home the following morning. I wasn't expecting much. We were pleasantly surprised. Our little room was clean and felt safe. We could open the windows! The bed and pillows were very comfortable. We slept great. The location was perfect; walked into town for a really good meal before heading to the show. The following morning breakfast restaurant just doors away was incredible! This hotel is out of the 60's in its character and charm. The one man operation is very efficient in responding to the check-in buzzer and to answering the phone for a quick question. We didn't use the shower or the TV; so I can't say anything about that."

Chambery Inn

8/10 Good

"This is a charming little inn. We enjoyed a cozy suite with a fireplace and a hot tub. The bed was very comfortable and the doorside delivery of hot coffee and a continental breakfast in a cute picnic basket was a nice touch. Although the room was at the basement level (with small windows at the top of the ceiling), the fireplace added nice ambiance. The bathroom soaps and shampoo were a bit basic, but absolutely serviceable. And while we never met the innkeepers, they had left the keys and a useful packet of information for us when we arrived. This was a nice location for our two day stay to experience music at Tanglewood. I would stay here again."

Devonfield Inn B&B

10/10 Excellent

"Wonderful location and hosts are amazing. Breakfast was great. Clean."

Pilgrim Inn

10/10 Excellent

"Wonderful fantastic "

More cheap stays in Lee

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

1.606.651 ₫

1.794.629 ₫ total

12 Oct - 13 Oct

includes taxes & fees

5.4/10 (922 reviews)

Quality Inn Great Barrington

372 Main Street Great Barrington MA

1.958.252 ₫

2.187.368 ₫ total

1 Nov - 2 Nov

includes taxes & fees

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA

2.043.888 ₫

2.283.022 ₫ total

18 Oct - 19 Oct

includes taxes & fees

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

1055 South Street Pittsfield MA

2.561.328 ₫

2.861.003 ₫ total

8 Nov - 9 Nov

includes taxes & fees

9.2/10 Wonderful! (234 reviews)

The Yankee Inn

461 Pittsfield Rd Lenox MA

2.742.432 ₫

3.063.296 ₫ total

1 Nov - 2 Nov

includes taxes & fees

The Whitlock

16 Church St Lenox MA

3.803.184 ₫

4.248.157 ₫ total

2 Nov - 3 Nov

includes taxes & fees

8.4/10 Very good! (395 reviews)

Hotels in Lee with star rating

Frequently asked questions

What's the seasonal weather like in Lee?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Lee are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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Book Hotels in Lee on Expedia.com

Find hotels in Lee, MA from 1.794.629 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Lee

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Lee hotels

1. Quality Inn Lee - Lenox South

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

3. Courtyard by Marriott Lenox Berkshires

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

5. The Yankee Inn

6. The Red Lion Inn

7. The Cornell Inn, Lenox & The Berkshires

8. The Whitlock

9. Chambery Inn

10. Berkshires Untold

11. Devonfield Inn B&B

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

13. Sunset Inn

14. Hilton Garden Inn Lenox Pittsfield

15. Hampton Inn & Suites Berkshires-Lenox

16. Berkshire Mountain Lodge

17. Brook Farm Inn

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

19. Econo Lodge Lee - Great Barrington

20. The Inn at Stockbridge

Stay near popular Lee attractions

Goose Pond Reservation

Lee Premium Outlets

Berkshire Scenic Railway Museum

Wood's Pond

Tyringham Cobble

McLennan Reservation

Lee Library

Ashintully Gardens

Learn more about Lee

Top Lee Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Berkshire Lake Lodge

Quality Inn Lee - Lenox South

Sunset Inn

Chambery Inn

Devonfield Inn B&B

Pilgrim Inn

More cheap stays in Lee

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 Lee with star rating

Frequently asked questions

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