A lush green landscape with a lake and rolling hills under a cloudy sky.

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for South Lee holiday homes

Interior

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, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is £351
includes taxes & fees
13 Jul - 14 Jul
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Outdoor spa tub

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, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is £342
includes taxes & fees
6 Jul - 7 Jul
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (18 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 £244
includes taxes & fees
13 Jul - 14 Jul
Cozy Riverside Berkshires Retreat
Fridge, microwave, stovetop, dishwasher

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.6 out of 10, Exceptional, (4 reviews)
"The host was extremely communicative and went above and beyond to ensure guest comfort."
United States
Diego G.
The price is £414
includes taxes & fees
8 Jul - 9 Jul
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Smart TV

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
10.0 out of 10, Exceptional, (1 review)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is £274
includes taxes & fees
10 Jul - 11 Jul
stylish Berkshires Retreat
Interior

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is £266
includes taxes & fees
16 Jul - 17 Jul
Real Estate: Therapy - Lake, Laundry, Love it
Property grounds

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.8 out of 10, Exceptional, (9 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is £288
includes taxes & fees
7 Jul - 8 Jul
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (33 reviews)
"Adorable guest home in Great Barrington! Light and bright. Perfect space for our family of 4. Well equipped kitchen and easy walk to downtown and groceries at the co-op. Would definitely stay here again!"
United States
Julie J.
The price is £329
includes taxes & fees
19 Jul - 20 Jul
Home in Great Barrington
TV

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 £510
includes taxes & fees
6 Jul - 7 Jul
Treetop Hideaway in Tyringham
Outdoor dining

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
8.0 out of 10, Very good, (8 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is £438
includes taxes & fees
26 Jul - 27 Jul
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Exterior detail

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Old Chatham
10.0 out of 10, Exceptional, (3 reviews)
"We enjoyed our stay at this property. The hot tub was great and the home was immaculate!"
United States
Terri E.
The price is £417
includes taxes & fees
7 Jul - 8 Jul
8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!
Fridge, microwave, oven, stovetop

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
Spacious 5-bedroom house in charming Lee with WiFi
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is £381
includes taxes & fees
13 Jul - 14 Jul
Cheerful 3-bedroom cottage with woodstove
Fridge, microwave, stovetop, dishwasher

Berkshire House Stay: 5BR/5BA

Berkshire House Stay: 5BR/5BA
Lee
10.0 out of 10, Exceptional, (22 reviews)
"Wonderful stay, beautiful, well equipped and clean property. Highly recommend for an adult famiky getaway "
United States
jennifer r.
The price is £825
includes taxes & fees
13 Jul - 14 Jul
Berkshire House Stay: 5BR/5BA
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (7 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 £354
includes taxes & fees
6 Jul - 7 Jul
Sweet Cozy Victorian in Housatonic. Close to everything.
Outdoor dining

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (20 reviews)
"Really great host - communication was great. House is so close to skiing, can’t beat it "
United States
Stephanie B.
The price is £866
includes taxes & fees
7 Jul - 8 Jul
Hancock Village Inn Near Jiminy Peak
TV, fireplace, printers

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, (6 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 £987
includes taxes & fees
13 Jul - 14 Jul
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Smart TV, books

Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
8.0 out of 10, Very good, (1 review)
"This older home was beautifully renovated and was able to easily accommodate our large group."
United States
Beth S.
The price is £482
includes taxes & fees
13 Jul - 14 Jul
Spacious Central Berkshires Home for Groups
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The location was excellent, within walking distance of ski trail. Wonderful view of the ski area and surrounding mountains. The fireplace was perfect for the end of the day. Our large family had plenty of space to have fun together or chill alone. We had concerns about the cleanliness and working conditions of some electronics. Our concerns were communicated with the owner, and the response was positive. I am sure with corrections this Comfortable Berkshire Retreat will be a 5 star stay. "
United States
Russell R.
The price is £419
includes taxes & fees
6 Jul - 7 Jul
Comfortable Berkshires retreat on mtn resort, SISO
Pool

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Hancock
9.8 out of 10, Exceptional, (74 reviews)
"Helpful host, lovely condo. Great location. Clean, tons of games and movies in unit. Also plenty of coffee pods included!"
United States
Christy F.
The price is £469
includes taxes & fees
7 Jul - 8 Jul
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
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 South Lee Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"A lovely stay at the Black Swan hotel in Lee for my birthday. Room was nice and comfortable, sweet balcony area to watch the sunset over the lake. Close to many attractions, ie, Norman Rockwell museum, outlets, pretty town, Botanical gardens and more. Would definitely go back again. Thank you"
rose 2-night trip
Posted 7 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about South Lee

South Lee Holiday Homes information

Number of reviews
278
Accommodation
441 Holiday Homes
Lowest Price
£244
Highest Price
£987