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

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Lee holiday homes

A living room with a brown leather sofa, two grey armchairs, a glass coffee table, and a wooden side table with a lamp.

1. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.2 out of 10, Wonderful, (5 reviews)
The price is £273
includes taxes & fees
8 Sept - 9 Sept
stylish Berkshires Retreat
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

2. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is £236
includes taxes & fees
1 Sept - 2 Sept
Cozy Riverside Berkshires Retreat
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.

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

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (7 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is £280
includes taxes & fees
8 Sept - 9 Sept
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

4. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"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!! "
United States
Samantha G.
The price is £425
includes taxes & fees
23 Sept - 24 Sept
Treetop Hideaway in Tyringham
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

5. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is £294
includes taxes & fees
6 Sept - 7 Sept
Home in Great Barrington
A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

6. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is £643
includes taxes & fees
2 Sept - 3 Sept
Stylish Mid-century Modern Berkshires Cape
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is £396
includes taxes & fees
8 Sept - 9 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

8. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (39 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveller
The price is £682
includes taxes & fees
20 Sept - 21 Sept
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A wooden deck with a table and chairs, surrounded by a white railing.

9. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.4 out of 10, Very good, (10 reviews)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is £396
includes taxes & fees
27 Aug - 28 Aug
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is £222
includes taxes & fees
13 Sept - 14 Sept
Real Estate: Therapy - Lake, Laundry, Love it
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

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

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
United States
Joanna P.
The price is £156
includes taxes & fees
26 Aug - 27 Aug
NEW RENO - Chalet-style farm loft near Tanglewood
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is £234
includes taxes & fees
3 Sept - 4 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.
A hot tub with a string of lights above it, set against a dark night sky.

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

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is £282
includes taxes & fees
26 Aug - 27 Aug
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A spacious living room with a dining area, a kitchen, and a large window.

14. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is £177
includes taxes & fees
14 Sept - 15 Sept
1800s Carriage house in Berkshires / Hudson Valley
A wooden deck with a staircase leading to a covered porch area.

15. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (35 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is £107
includes taxes & fees
26 Aug - 27 Aug
All the comforts of home
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

16. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.8 out of 10, Exceptional, (7 reviews)
"excellent communication with property manager."
United States
Nancy H.
The price is £406
includes taxes & fees
29 Aug - 30 Aug
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A white two-story house with a porch, surrounded by trees and a hill.

17. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is £397
includes taxes & fees
9 Sept - 10 Sept
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A camping setup with a metal chair and a table by a river in a forest.

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (12 reviews)
The price is £253
includes taxes & fees
20 Sept - 21 Sept
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

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

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house with great amenities in a convenient location. We loved the open concept that provided a great space for cooking, hanging out and playing games together while enjoying a beautiful view. The gameroom was so much fun, and we’d love to visit again when the sauna is finished. Our family of 6 and family dog loved it!"
United States
Rebecca K.
The price is £961
includes taxes & fees
27 Aug - 28 Aug
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A house with a porch, a garden with pink flowers, and a stone wall along the road.

20. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (149 reviews)
"Great location"
United States
Will G.
The price is £244
includes taxes & fees
23 Sept - 24 Sept
Big farmhouse in the foothills of the Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Lee Hotel Reviews

Sunset Inn

Sunset Inn

10/10 Excellent
"The host of the property was very friendly and helpful. A real gentleman ! The bed was new and perfect for my back. It was clean and quiet and a great nights sleep. Very happy traveler."
Mark 1-night trip
Posted 7 hours ago
Sunset Inn

Find out more about Lee

Lee Holiday Homes information

Number of reviews
332
Accommodation
157 Holiday Homes
Lowest Price
£107
Highest Price
£961