Lee Holiday Rentals

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Our top choices for Lee holiday rentals

9.4 out of 10, Exceptional, (40)
"It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host."
United States
Roy
The price is NZ$356
includes taxes & fees
2 Jan - 3 Jan 2026
Charming Apt in 18th c Berkshire Farmhouse

Holiday Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is NZ$441
includes taxes & fees
5 Jan - 6 Jan 2026
Home in Great Barrington
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is NZ$641
includes taxes & fees
4 Jan - 5 Jan 2026
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
The price is NZ$551
includes taxes & fees
11 Jan - 12 Jan 2026
3-bedroom house in beautiful Berkshires, close to amenities!
9.4 out of 10, Exceptional, (3)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is NZ$787
includes taxes & fees
4 Jan - 5 Jan 2026
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Holiday Home in Great Barrington

Family Ski Getaway in the Berkshires
9.4 out of 10, Exceptional, (6)
"The host was exceptional and so kind. The location was in close proximity to 3 quaint New England small towns whose downtowns had many restaurants and local shops to enjoy-Great Barrington (GB Eats for breakfast), Stockbridge (best shopping) and Lenox (exceptional dinner at Frankie’s Italian). The house looked updated on the outside but inside looked like early 1900s with a hint of Victorian influence. My only caution is for anyone with mobility issues as all 3 bedrooms and the only (very small)...
United States
Kathy C.
The price is NZ$510
includes taxes & fees
4 Jan - 5 Jan 2026
Family Ski Getaway in the Berkshires
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is NZ$846
includes taxes & fees
3 Jan - 4 Jan 2026
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Holiday Home in Great Barrington

Great Barrington Get Away
9.4 out of 10, Exceptional, (26)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
The price is NZ$949
includes taxes & fees
4 Jan - 5 Jan 2026
Great Barrington Get Away
8.0 out of 10, Very good, (2)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is NZ$1,568
includes taxes & fees
5 Jan - 6 Jan 2026
Spacious 5-bedroom house in charming Lee with WiFi

Holiday Home in Great Barrington

Cozy. Clean. Free bagel shop. 3 Fireplaces.
10.0 out of 10, Exceptional, (1)
"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 NZ$1,007
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy. Clean. Free bagel shop. 3 Fireplaces.
9.6 out of 10, Exceptional, (67)
"We had a lovely stay! The studio was comfortable, clean, and just what we needed. Our hosts were friendly and helpful!"
United States
Janice L.
The price is NZ$354
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy Rustic Apt in 18th c Berkshire Farmhouse
9.0 out of 10, Wonderful, (22)
"I loved staying here the weekend with my friends, the owner Patrick was so accommodating and helpful!"
United States
Mckenna d.
The price is NZ$377
includes taxes & fees
11 Jan - 12 Jan 2026
Bright Boho Apt in 18th c Berkshire Farmhouse
2.0 out of 10, (1)
"THIS. PLACE. IS. A. DUMP. Do NOT STAY HERE under any circumstances."
United States
Michael
The price is NZ$350
includes taxes & fees
29 Dec - 30 Dec
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (3)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is NZ$642
includes taxes & fees
7 Jan - 8 Jan 2026
Sugar Shack - 300 square feet of pure sweetness.
10.0 out of 10, Exceptional, (6)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is NZ$638
includes taxes & fees
5 Jan - 6 Jan 2026
BLUSH: Boutique TINY home*private spa*walk to town

Camping in Williamstown

Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is NZ$388
includes taxes & fees
4 Jan - 5 Jan 2026
Huttopia Berkshires
3.0 star property
8.8 out of 10, Excellent, (2188)
"Awesome for ski"
United States
Lazar
The price is NZ$218
includes taxes & fees
4 Jan - 5 Jan 2026
Vacation Village in the Berkshires
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 NZ$314
includes taxes & fees
29 Dec - 30 Dec
Taborton Harvest Boulder Pines Cabin in the woods

Aparthotel in Hudson

Micosta Leisure Inn
3.0 star property
9.4 out of 10, Exceptional, (133)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
The price is NZ$249
includes taxes & fees
30 Dec - 31 Dec
Micosta Leisure Inn

Apartment in Hudson

All comforts of home
9.8 out of 10, Exceptional, (52)
"Loved the place and would love to come back. "
United States
Georgine
The price is NZ$227
includes taxes & fees
6 Jan - 7 Jan 2026
All comforts of 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

Find out more about Lee

Everything you need to know about Lee holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Lee holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Lee holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Lee holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Lee. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Lee holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Lee holiday rentals we have selected for you start as low as NZ$218 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Lee rentals

At Expedia, we put the best Lee holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Lee rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Lee holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Lee. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Peace and quiet on the lake: This holiday home rental outside of Lee is located on a lake, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

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.