Lee Vacation Rentals from CA $804: Short-Term Rentals for 2026

Q: What are some of the best vacation home rentals that Lee has to offer?

Experience Three Sisters Sanctuary in Goshen, MA : This vacation home rental outside of Lee is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

Check prices for these dates

In two weeks

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Our top choices for Lee vacation rentals

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Pittsfield

CA $168 total

includes taxes & fees

Nov 9 - Nov 10

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Great Barrington

Deborah S.

CA $199 total

includes taxes & fees

Oct 18 - Oct 19

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.

3. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Sherwood Forest

CA $551 total

includes taxes & fees

Oct 14 - Oct 15

A modern living room with a sofa, armchair, coffee table, and TV.

4. Spacious Central Berkshires Home for Groups

Lee

Beth S.

CA $840 total

includes taxes & fees

Oct 12 - Oct 13

A living room with a sofa, armchairs, a coffee table, and a television.

5. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

CA $904 total

includes taxes & fees

Oct 19 - Oct 20

A staircase with a wooden handrail and a white wall with a light switch.

6. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

CA $437 total

includes taxes & fees

Oct 27 - Oct 28

A sandy beach with a lake and forest in the background.

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

Great Barrington

Marc R.

CA $464 total

includes taxes & fees

Oct 12 - Oct 13

A covered outdoor seating area with two chairs and a view of a grassy landscape.

8. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Lenox

CA $453 total

includes taxes & fees

Oct 11 - Oct 12

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

9. Home in Great Barrington

Great Barrington

HEATHER G.

CA $496 total

includes taxes & fees

Oct 13 - Oct 14

A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

10. Stylish Mid-century Modern Berkshires Cape

Lee

H B.

CA $1,242 total

includes taxes & fees

Oct 18 - Oct 19

A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

11. Treetop Hideaway in Tyringham

Monterey

"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!! "

Samantha G.

CA $804 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with a central island, stainless steel appliances, and a ceiling fan.

12. Urban Peak Escape, Lenox, MA

Lenox

Nancy H.

CA $1,084 total

includes taxes & fees

Oct 14 - Oct 15

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.

13. Ellie’s Overlook, best view in the Berkshires!

Richmond

CA $989 total

includes taxes & fees

Oct 15 - Oct 16

A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

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

Great Barrington

Mark M.

CA $999 total

includes taxes & fees

Oct 19 - Oct 20

A wooden deck with a table and chairs, surrounded by a white railing.

15. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Stephen L.

CA $699 total

includes taxes & fees

Oct 14 - Oct 15

A recreational vehicle with a beige sofa, pillows, a small table, and potted plants.

16. Cozy Camper tucked into the woods

Sandisfield

"This was a completely hidden gem. I stayed here for one night because I was visiting a friend but I wished I had booked it longer. My friend and I ended up staying here the whole time. I woke up to the sounds of crickets and chickens, and had fresh eggs for breakfast. Then I went for a hike in the pristine woods. Matt and Grace offered to let me use the paddle boards to enjoy the lake! It was a total vacation… no need to go anywhere else. The camper itself was extremely clean and adorably...

hannah w.

CA $286 total

includes taxes & fees

Nov 3 - Nov 4

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

17. Vacation Village in the Berkshires

Williamstown

Denton

CA $143 total

includes taxes & fees

Nov 2 - Nov 3

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

18. Micosta Leisure Inn

Hudson

CA $159 total

includes taxes & fees

Oct 13 - Oct 14

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Sherwood Forest

William C B.

CA $480 total

includes taxes & fees

Nov 3 - Nov 4

A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

20. NEW RENO - Chalet-style farm loft near Tanglewood

New Lebanon

Joanna P.

CA $295 total

includes taxes & fees

Oct 12 - Oct 13

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Top Lee Hotel Reviews

Quality Inn Lee - Lenox South

10/10 Excellent

"My wife and I were touring the Berkshires near the end of a long road trip. We’re so glad we chose this Quality Inn in Lee for our stay! Staff in the afternoon/evening, at breakfast, and at the morning desk were all professional, friendly, and helpful. Our room was very clean and comfortable, and the amenities worked well. The continental breakfast included not only stations for waffles and toast, it also included tasty Jimmy Dean breakfast sandwiches to microwave. Coffee and tea and hot chocolate were available 24/7. Art related to nature and the Berkshires was on the walls. A highly recommended property!"

Lake View Berkshire Retreat – Private Setting Near Lenox

10/10 Excellent

"Kari was so flexible and had open lines of communication the entire time we were there. There was an unforeseen circumstance that arose and Kari made sure we were kept in the loop, offered multiple solutions, and was just great! The house itself is beautiful and I can only imagine what it’s like during the summertime, if we’re ever back in the Berkshire’s we’d love to stay with Kari and everyone again"

Gateway to the Berkshires - Renovated downtown apartment

10/10 Excellent

"This is an excellent space! It’s well laid out and functional, with everything you need in an apartment. It’s right on Lee’s main drag so we could walk to everything, including coffee, restaurants, and thrifting and antiquing."

Sunset Inn

8/10 Good

"We were in town for a show at Tanglewood in Lenox. Concert had been rescheduled with little notice; so it put us in a tight spot with no time to add time to being in the Berkshires. I just looked for an inexpensive overnight to just sleep before heading back home the following morning. I wasn't expecting much. We were pleasantly surprised. Our little room was clean and felt safe. We could open the windows! The bed and pillows were very comfortable. We slept great. The location was perfect; walked into town for a really good meal before heading to the show. The following morning breakfast restaurant just doors away was incredible! This hotel is out of the 60's in its character and charm. The one man operation is very efficient in responding to the check-in buzzer and to answering the phone for a quick question. We didn't use the shower or the TV; so I can't say anything about that."

Berkshire Lake at the Pillow, and EV!

10/10 Excellent

"The house was really nice, the rooms were spacious the beds were comfortable, the kitchen was well stocked and open concept with the dining room and living room. There is a large game room in the basement that is probably put to good use by others but we just were out on trails and around the different towns all day. The lake is tight across the highway( not great) but it was lovely and there are kayaks you can use and a canoe. The host seem very nice and accommodating."

Find out more about Lee

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Lee. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Lee?

Yes, you can find vacation rentals in Lee near Berkshire Scenic Railway Museum, or you can go with 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 vacation home rentals that Lee has to offer?

Experience Three Sisters Sanctuary in Goshen, MA: This vacation home rental outside of Lee is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay.

How many vacation rentals are there in Lee?

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

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 Lee Premium Outlets and Lee Library.

What are vacation rentals like in Lee?

Vacation rentals are privately owned properties you can book for several days or longer in Lee. Vacation rentals feature amenities such as WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a small group gathering.

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Check prices for these dates

Our top choices for Lee vacation rentals

1. Berkshire Mountain Lodge

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

3. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

4. Spacious Central Berkshires Home for Groups

5. Sun Filled Lenox Retreat - Minutes to Tanglewood!

6. Leaf-Peeper Paradise in the Berkshires

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

8. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

9. Home in Great Barrington

10. Stylish Mid-century Modern Berkshires Cape

11. Treetop Hideaway in Tyringham

12. Urban Peak Escape, Lenox, MA

13. Ellie’s Overlook, best view in the Berkshires!

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

15. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

16. Cozy Camper tucked into the woods

17. Vacation Village in the Berkshires

18. Micosta Leisure Inn

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

20. NEW RENO - Chalet-style farm loft near Tanglewood

Find vacation rentals that suit your style

Top Lee Hotel Reviews

Quality Inn Lee - Lenox South

stylish Berkshires Retreat

Modern And Spacious Berkshires Retreat 5 bdrm 3 bath

Lake View Berkshire Retreat – Private Setting Near Lenox

Gateway to the Berkshires - Renovated downtown apartment

Sunset Inn

Berkshire Lake at the Pillow, and EV!

Goose Pond Landings | Private Dock • Kayaks

Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!

Find out more about Lee

Frequently asked questions

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