Lee Holiday Rentals

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Check prices for these dates

Tonight
19 Dec - 20 Dec
Tomorrow
20 Dec - 21 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Lee holiday rentals

Terrace/patio
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Lee
9.4 out of 10, Exceptional, (71)
"Wonderful time !! Location was perfect and we really enjoyed our time here "
United States
Sue P.
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2175)
"Awesome for ski"
United States
Lazar
The price is HK$809
HK$989 total
includes taxes & fees
4 Jan - 5 Jan 2026
Vacation Village in the Berkshires
Exterior
Huttopia Berkshires

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is HK$1,505
HK$1,682 total
includes taxes & fees
4 Jan - 5 Jan 2026
Huttopia Berkshires
Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

The Ponds at Foxhollow
3.0 star property
Lenox
8.6 out of 10, Excellent, (136)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
United States
Cyril
The Ponds at Foxhollow
Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort
3.0 star property
Hancock
8.2 out of 10, Very good, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is HK$1,704
HK$1,903 total
includes taxes & fees
4 Jan - 5 Jan 2026
Jiminy Peak Mountain Resort
Balcony
Micosta Leisure Inn

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (132)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
The price is HK$1,011
HK$1,132 total
includes taxes & fees
21 Dec - 22 Dec
Micosta Leisure Inn
Exterior detail
Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (13)
"Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "
United States
Joanna R.
The price is HK$972
HK$1,425 total
includes taxes & fees
20 Dec - 21 Dec
Taborton Harvest Boulder Pines Cabin in the woods
Games room
Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires
Great Barrington
9.4 out of 10, Exceptional, (6)
The price is HK$1,575
HK$2,316 total
includes taxes & fees
21 Dec - 22 Dec
Family Ski Getaway in the Berkshires
Interior
Peace and quiet on the lake

Peace and quiet on the lake

Peace and quiet on the lake
Sherwood Forest
9.6 out of 10, Exceptional, (230)
"Great communication, comfortable home, love the location"
United States
Susan C.
Peace and quiet on the lake
Exterior detail
The Kemble- Built by a US Secretary of State in Lenox

The Kemble- Built by a US Secretary of State in Lenox

The Kemble- Built by a US Secretary of State in Lenox
Lenox
10.0 out of 10, Exceptional, (18)
"Perfect house for our family reunion. Everything was perfect."
United States
Michael C.
The Kemble- Built by a US Secretary of State in Lenox
Exterior
Beautiful 5-star Estate! Pool, Pond, Game Room, Gym, Library, Party Barn, Trails

Beautiful 5-star Estate! Pool, Pond, Game Room, Gym, Library, Party Barn, Trails

Beautiful 5-star Estate! Pool, Pond, Game Room, Gym, Library, Party Barn, Trails
Old Chatham
9.6 out of 10, Exceptional, (93)
"This was a perfect location for our 20 person college reunion. The premises were clean and Laurie was very accommodating and responsive to all my emails and requests. Thank you for sharing the estate with us."
United States
Leicia S.
Beautiful 5-star Estate! Pool, Pond, Game Room, Gym, Library, Party Barn, Trails
Terrace/patio
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach
Coxsackie
10.0 out of 10, Exceptional, (168)
"Had an absolutely amazing time here! Jody was very prompt with responding to any questions we had during the duration of our stay. The house was so perfect. 5 Stars!!"
United States
Steve B.
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach
Smart TV, fireplace, DVD player
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Great Barrington
10.0 out of 10, Exceptional, (28)
"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "
United States
Johnathan B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
9.0 out of 10, Wonderful, (7)
"Kind and responsive host."
United States
Javier
The price is HK$2,505
HK$5,699 total
includes taxes & fees
20 Dec - 21 Dec
Comfortable Berkshires retreat on mtn resort, SISO
Exterior
Bear Creek Cabin

Bear Creek Cabin

Bear Creek Cabin
Charlemont
10.0 out of 10, Exceptional, (43)
"We enjoyed our stay!!"
United States
Hillary S.
The price is HK$3,112
HK$4,685 total
includes taxes & fees
20 Dec - 21 Dec
Bear Creek Cabin
Dining
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Stockbridge
10.0 out of 10, Exceptional, (135)
"Clean house, well appointed, great location, responsive owner"
United States
sara m.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Smart TV, fireplace, DVD player, music library
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Pownal
9.4 out of 10, Exceptional, (85)
"This unique hideaway was great for our family. The open layout might not work for everyone, but suited us just fine! We were only here a couple nights but enjoyed the location and using the hot tub! "
United States
Elizabeth R.
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Fridge, microwave, oven, stovetop
Amore Estate - beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.
Lenox
9.2 out of 10, Wonderful, (33)
"Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back."
United States
Jacquie S.
Amore Estate - beautiful room with many places to explore and relax in.
Fridge, microwave, oven, stovetop
Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience
Sand Lake
10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
United States
Georgia M.
The price is HK$972
HK$1,425 total
includes taxes & fees
20 Dec - 21 Dec
Taborton Harvest Timber Trails Unique cabin experience
Property grounds
The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.

The Creation Station is a cozy place so make yourself at home.
Easthampton Ma.
10.0 out of 10, Exceptional, (72)
"The place is wonderful. Our 2nd visit and will be back. Has everything you need and then some. For us its centrally located so more family came for day trips. "
United States
Connie P.
The price is HK$1,400
HK$2,181 total
includes taxes & fees
24 Dec - 25 Dec
The Creation Station is a cozy place so make yourself at home.
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

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

10/10 Excellent
"Roberto was an excellent host!! Very attentive to our needs and concerns "
Robert W. 4-night trip
Posted 10 days ago
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Find out more about Lee

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

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

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

Frequently asked questions

Can I find a holiday rental in Lee?

Yes, there are holiday rentals in Lee close to Berkshire Scenic Railway Museum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and museums in Lee. Leave plenty of time to check out the shops and lakeside during your trip.

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

Spacious 5-bedroom house in charming Lee with WiFi: This highly rated holiday home rental in Lee offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 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 Lee?

Choose from 44 Expedia holiday rentals in Lee for a memorable holiday.

What can I see and do in Lee?

Cultural attractions include Berkshire Scenic Railway Museum and Animagic Museum of Animation, whereas Goose Pond Reservation and Housatonic River are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Berkshire Mountain Country Store and Lee Premium Outlets.

What are holiday rentals like in Lee?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Lee. Holiday rentals offer amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a family trip.