Lee Holiday Homes from £110: Search Holiday Homes in Lee

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.

includes taxes & fees

14 Oct - 15 Oct

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

2. Spacious Central Berkshires Home for Groups

Lee

Beth S.

includes taxes & fees

12 Oct - 13 Oct

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

3. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

includes taxes & fees

19 Oct - 20 Oct

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

4. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

includes taxes & fees

26 Oct - 27 Oct

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

5. Stylish Mid-century Modern Berkshires Cape

Lee

H B.

includes taxes & fees

18 Oct - 19 Oct

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

6. 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.

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

7. Home in Great Barrington

Great Barrington

Janet G.

includes taxes & fees

13 Oct - 14 Oct

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

includes taxes & fees

14 Oct - 15 Oct

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Top Lee Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"Nice motel located on Laurel Lake. Convenient location. We did not upgrade to a room with a view of lake, but should consider. Lovely breakfast with big windows on the lake. Everything worked fine, would stay again."

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!"

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."

Find out more about Lee

Lee Holiday Homes information

Number of reviews	211
Accommodation	157 Holiday Homes
Lowest Price	£110
Highest Price	£1,000

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Lee holiday homes

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

2. Spacious Central Berkshires Home for Groups

3. Sun Filled Lenox Retreat - Minutes to Tanglewood!

4. Leaf-Peeper Paradise in the Berkshires

5. Stylish Mid-century Modern Berkshires Cape

6. Treetop Hideaway in Tyringham

7. Home in Great Barrington

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

9. Cozy. Clean. Free bagel shop. 3 Fireplaces.

10. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

11. Real Estate: Therapy - Lake, Laundry, Love it

12. NEW RENO - Chalet-style farm loft near Tanglewood

13. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

14. 1800s Carriage house in Berkshires / Hudson Valley

15. Sweet Cozy Victorian in Housatonic. Close to everything.

16. All the comforts of home

17. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

18. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

19. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

20. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Find holiday rentals that suit your style

Top Lee Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Quality Inn Lee - Lenox South

stylish Berkshires Retreat

Modern And Spacious Berkshires Retreat 5 bdrm 3 bath

Lake View Berkshire Retreat – Private Setting Near Lenox

Gateway to the Berkshires - Renovated downtown apartment

Sunset Inn

Berkshire Lake at the Pillow, and EV!

Goose Pond Landings | Private Dock • Kayaks

Find out more about Lee

Lee Holiday Homes information

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