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

South Lee Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for South Lee holiday rentals

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

1. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (29 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is HK$2,974
HK$5,452 total
includes taxes & fees
20 Oct - 21 Oct
Secluded Family Home in Serene Stockbridge Woods
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,196 reviews)
"Our visit was very nice. Facilities were beautiful!"
United States
marilyn
The price is HK$673
HK$927 total
includes taxes & fees
9 Nov - 10 Nov
Berkshire Mountain Lodge
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

3. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,729 reviews)
"Very pleased with our stay -great place for the family we will G-d willing return"
United States
Denton
The price is HK$630
HK$790 total
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the Berkshires
A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

4. 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 HK$3,991
HK$6,850 total
includes taxes & fees
18 Oct - 19 Oct
Stylish Mid-century Modern Berkshires Cape
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

5. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (8 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is HK$883
HK$1,293 total
includes taxes & fees
30 Oct - 31 Oct
Cozy 1-bedroom studio in serene Great Barrington with AC
A modern living room with a sofa, armchair, coffee table, and TV.

6. 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 HK$2,295
HK$4,624 total
includes taxes & fees
13 Oct - 14 Oct
Spacious Central Berkshires Home for Groups
A staircase with a wooden handrail and a white wall with a light switch.

7. 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 HK$1,530
HK$2,411 total
includes taxes & fees
26 Oct - 27 Oct
Leaf-Peeper Paradise in the Berkshires
A sandy beach with a lake and forest in the background.

8. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (6 reviews)
"Amazing apartment! Clean, large, close walk to downtown Great Barrington. Joseph was an incredible host - accurate description, great communication. Will definitely be back!"
United States
Marc R.
The price is HK$1,640
HK$2,586 total
includes taxes & fees
15 Oct - 16 Oct
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A living room with a sofa, armchairs, a coffee table, and a television.

9. 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 HK$2,770
HK$5,338 total
includes taxes & fees
9 Nov - 10 Nov
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

10. 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 HK$1,570
HK$2,752 total
includes taxes & fees
13 Oct - 14 Oct
Sweet Cozy Victorian in Housatonic. Close to everything.
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 HK$549
HK$1,632 total
includes taxes & fees
14 Oct - 15 Oct
NEW RENO - Chalet-style farm loft near Tanglewood
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

12. 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 HK$2,119
HK$3,200 total
includes taxes & fees
22 Oct - 23 Oct
Home in Great Barrington
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

13. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is HK$691
HK$1,790 total
includes taxes & fees
12 Oct - 13 Oct
Berkshires Apartment at the Stephentown Hotel
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.

14. 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 HK$1,158
HK$2,959 total
includes taxes & fees
14 Oct - 15 Oct
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.

15. 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 HK$2,127
HK$4,430 total
includes taxes & fees
9 Nov - 10 Nov
Treetop Hideaway in Tyringham
A spacious living room with a dining area, a kitchen, and a large window.

16. 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 HK$667
HK$1,768 total
includes taxes & fees
2 Nov - 3 Nov
1800s Carriage house in Berkshires / Hudson Valley
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

17. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is HK$890
HK$1,923 total
includes taxes & fees
14 Oct - 15 Oct
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

18. 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 HK$589
HK$2,481 total
includes taxes & fees
3 Nov - 4 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A snow-covered outdoor area with a fire pit, tables, and chairs.

19. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is HK$939
HK$1,987 total
includes taxes & fees
14 Oct - 15 Oct
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A hot tub with a string of lights above it, set against a dark night sky.

20. 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 HK$1,257
HK$2,982 total
includes taxes & fees
12 Oct - 13 Oct
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Lee Hotel Reviews

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"My daughter and I stayed at this Inn for a girls weekend and it was a perfect way to kick off our fall weekend. From great service to delicious breakfast everything was taken care of."
Leslie K 1-night trip
Posted less than an hour ago
The Cornell Inn, Lenox & The Berkshires

Find out more about South Lee

Search for holiday rentals in South Lee on Expedia! You can easily find your home rentals, villas, holiday apartments in South Lee using one of the methods below:

  • View our selection of featured holiday rentals in South Lee
  • Use the map to find apartments and other holiday homes in the South Lee neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in South Lee while they last

Look no further and take a look at our great range of rental properties in South Lee!

Frequently asked questions

Are there holiday rentals in South Lee?

Yes, there are holiday rentals close to the most popular sights in South Lee, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say South Lee has a good selection of restaurants and the local cheese shops. Make sure you have time to check out the ski areas and shopping during your trip.

What are some of the best holiday rentals that South Lee has to offer?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of South Lee is located near skiing, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in South Lee?

Choose from 7 Expedia holiday rentals in South Lee for a memorable holiday.

What’s there to see and do in South Lee?

While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Housatonic River. Chesterwood and National Shrine of the Divine Mercy are a couple of places you'll find in the wider area.

What’s a holiday rental in South Lee like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in South Lee. Holiday rentals feature extras such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.