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

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Lee vacation 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!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥23,367
￥59,699 total
includes taxes & fees
Oct 14 - Oct 15
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A modern living room with a sofa, armchair, coffee table, and TV.

2. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
9.4 out of 10, Exceptional, (3 reviews)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is ￥46,186
￥93,213 total
includes taxes & fees
Oct 12 - Oct 13
Spacious Central Berkshires Home for Groups
A living room with a sofa, armchairs, a coffee table, and a television.

3. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
10.0 out of 10, Exceptional, (11 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
United States
Patricia O.
The price is ￥50,295
￥100,387 total
includes taxes & fees
Oct 19 - Oct 20
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A staircase with a wooden handrail and a white wall with a light switch.

4. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (28 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is ￥30,870
￥48,629 total
includes taxes & fees
Oct 26 - Oct 27
Leaf-Peeper Paradise in the Berkshires
A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

5. 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 ￥80,501
￥138,195 total
includes taxes & fees
Oct 18 - Oct 19
Stylish Mid-century Modern Berkshires Cape
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

6. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 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 ￥42,902
￥89,356 total
includes taxes & fees
Nov 9 - Nov 10
Treetop Hideaway in Tyringham
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

7. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is ￥35,192
￥55,047 total
includes taxes & fees
Oct 13 - Oct 14
Home in Great Barrington
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!

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is ￥49,739
￥109,128 total
includes taxes & fees
Oct 14 - Oct 15
Ellie’s Overlook, best view in the Berkshires!
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is ￥63,160
￥109,704 total
includes taxes & fees
Oct 20 - Oct 21
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A wooden deck with a table and chairs, surrounded by a white railing.

10. 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 comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
United States
Stephen L.
The price is ￥42,491
￥77,976 total
includes taxes & fees
Oct 14 - Oct 15
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A bedroom with a bed, a desk, a chair, a ceiling fan, and a window.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.0 out of 10, Wonderful, (2 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is ￥14,211
￥52,914 total
includes taxes & fees
Nov 3 - Nov 4
Real Estate: Therapy - Lake, Laundry, Love it
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

12. 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 ￥12,823
￥34,847 total
includes taxes & fees
Oct 14 - Oct 15
NEW RENO - Chalet-style farm loft near Tanglewood
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, (18 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ￥25,296
￥60,002 total
includes taxes & fees
Oct 12 - Oct 13
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 ￥13,422
￥35,566 total
includes taxes & fees
Nov 2 - Nov 3
1800s Carriage house in Berkshires / Hudson Valley
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 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 ￥31,580
￥55,382 total
includes taxes & fees
Oct 20 - Oct 21
Sweet Cozy Victorian in Housatonic. Close to everything.
A wooden deck with a staircase leading to a covered porch area.

16. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"No frills, very clean and peaceful, beautiful setting"
United States
Lori M.
The price is ￥16,769
￥22,319 total
includes taxes & fees
Oct 13 - Oct 14
All the comforts of home
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 ￥35,778
￥79,484 total
includes taxes & fees
Nov 2 - Nov 3
1789 Shaker Farmhouse in Berkshires/Hudson Valley
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.

18. 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, (9 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is ￥89,814
￥210,028 total
includes taxes & fees
Oct 22 - Oct 23
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

19. 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, (8 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is ￥27,790
￥89,212 total
includes taxes & fees
Oct 14 - Oct 15
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
A camping setup with a metal chair and a table by a river in a forest.

20. 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, (15 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is ￥31,662
￥54,433 total
includes taxes & fees
Oct 12 - Oct 13
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
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

The Black Swan Lee - Lenox, an Ascend Collection Hotel

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."
Dianna 1-night trip
Posted 3 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Lee

Lee Vacation Homes information

Number of reviews
211
Accommodation
157 Vacation Homes
Lowest Price
￥22,319
Highest Price
￥210,028