Lee Vacation Homes

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

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Our top choices for Lee holiday homes

A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

1. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

Sharon K.

HK$2,944 total

includes taxes & fees

14 Oct - 15 Oct

A living room with a sofa, armchairs, a coffee table, and a television.

2. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

HK$4,976 total

includes taxes & fees

14 Oct - 15 Oct

A staircase with a wooden handrail and a white wall with a light switch.

3. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

HK$2,213 total

includes taxes & fees

26 Oct - 27 Oct

A modern living room with a sofa, armchair, coffee table, and TV.

4. Spacious Central Berkshires Home for Groups

Lee

Beth S.

HK$4,712 total

includes taxes & fees

13 Oct - 14 Oct

A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

5. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

HK$5,452 total

includes taxes & fees

20 Oct - 21 Oct

A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

6. Stylish Mid-century Modern Berkshires Cape

Lee

H B.

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

7. Treetop Hideaway in Tyringham

Monterey

"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "

Samantha G.

HK$4,421 total

includes taxes & fees

9 Nov - 10 Nov

A modern living room with a grey sectional sofa, a brown leather ottoman, a woven rug, a dining table with chairs, and a view through large windows.

8. Ellie’s Overlook, best view in the Berkshires!

Richmond

HK$5,424 total

includes taxes & fees

17 Oct - 18 Oct

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Top Lee Hotel Reviews

Quality Inn Lee - Lenox South

10/10 Excellent

"Good breakfast. Great location"

Lake View Berkshire Retreat – Private Setting Near Lenox

10/10 Excellent

"Kari was so flexible and had open lines of communication the entire time we were there. There was an unforeseen circumstance that arose and Kari made sure we were kept in the loop, offered multiple solutions, and was just great! The house itself is beautiful and I can only imagine what it’s like during the summertime, if we’re ever back in the Berkshire’s we’d love to stay with Kari and everyone again"

Gateway to the Berkshires - Renovated downtown apartment

10/10 Excellent

"This is an excellent space! It’s well laid out and functional, with everything you need in an apartment. It’s right on Lee’s main drag so we could walk to everything, including coffee, restaurants, and thrifting and antiquing."

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."

Berkshire Lake at the Pillow, and EV!

10/10 Excellent

"The house was really nice, the rooms were spacious the beds were comfortable, the kitchen was well stocked and open concept with the dining room and living room. There is a large game room in the basement that is probably put to good use by others but we just were out on trails and around the different towns all day. The lake is tight across the highway( not great) but it was lovely and there are kayaks you can use and a canoe. The host seem very nice and accommodating."

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