Lee Holiday Rentals from €498: Search Short-Term Rentals

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

Experience Three Sisters Sanctuary in Goshen, MA : This holiday 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

In two months

In three months

In four months

Our top choices for Lee holiday rentals

A hotel room with a sofa, armchair, TV, desk, and a large window with curtains.

1. Berkshire Mountain Lodge

Pittsfield

marilyn

includes taxes & fees

18 Oct - 19 Oct

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.

includes taxes & fees

14 Oct - 15 Oct

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

Sharon K.

includes taxes & fees

8 Oct - 9 Oct

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

4. Spacious Central Berkshires Home for Groups

Lee

Beth S.

includes taxes & fees

12 Oct - 13 Oct

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

5. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

includes taxes & fees

19 Oct - 20 Oct

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.

includes taxes & fees

26 Oct - 27 Oct

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.

includes taxes & fees

8 Oct - 9 Oct

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

includes taxes & fees

11 Oct - 12 Oct

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

9. Home in Great Barrington

Great Barrington

HEATHER G.

includes taxes & fees

13 Oct - 14 Oct

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.

includes taxes & fees

18 Oct - 19 Oct

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.

includes taxes & fees

4 Nov - 5 Nov

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

12. Urban Peak Escape, Lenox, MA

Lenox

Nancy H.

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

includes taxes & fees

14 Oct - 15 Oct

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.

includes taxes & fees

19 Oct - 20 Oct

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.

includes taxes & fees

13 Oct - 14 Oct

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.

includes taxes & fees

2 Nov - 3 Nov

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

includes taxes & fees

1 Nov - 2 Nov

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

18. Micosta Leisure Inn

Hudson

Kim

includes taxes & fees

13 Oct - 14 Oct

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.

includes taxes & fees

3 Nov - 4 Nov

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.

includes taxes & fees

8 Oct - 9 Oct

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Top Lee Hotel Reviews

Quality Inn Lee - Lenox South

8/10 Good

"Wonderful location. Nearby Norman Rockwell museum. Perfect for a stopover."

Berkshire Lake Lodge

10/10 Excellent

"It was the sweetest Place ever. It was compact yet cute and efficient. Great shower and plenty of hot water. It was easy to check in and clean. There were all the amenities that we needed. The owner was very nice and even started a fire in the cute fire pit. We enjoyed the scenery and the pretty lake setting. Than-you for a pleasant experience in Mass. I"

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

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, apart-hotels, 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 €498 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.

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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?

Experience Three Sisters Sanctuary in Goshen, MA: This holiday 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 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 Lee Premium Outlets and Lee Library.

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.

Holiday Rentals in Lee

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Treat yourself

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Check prices for these dates

Our top choices for Lee holiday 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 holiday rentals that suit your style

Top Lee Hotel Reviews

Quality Inn Lee - Lenox South

Find out more about Lee

Explore a world of travel with Expedia

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