Lee Vacation Rentals from $577: Search Short-Term Rentals

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.

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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

Robert

$108 nightly

Oct 22 - Oct 23

Total with taxes and fees

A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

2. Riverside Retreat in the Berkshires

Great Barrington

Kelly B.

$284 nightly

Sep 23 - Sep 24

Total with taxes and fees

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

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

Great Barrington

Shelly B.

$148 nightly

Sep 29 - Sep 30

Total with taxes and fees

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.

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

Sherwood Forest

Sharon K.

$335 nightly

Sep 28 - Sep 29

Total with taxes and fees

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

5. 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.

$546 nightly

Sep 23 - Sep 24

Total with taxes and fees

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

6. Home in Great Barrington

Great Barrington

HEATHER G.

$294 nightly

Sep 24 - Sep 25

Total with taxes and fees

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

Kristin O.

$293 nightly

Sep 23 - Sep 24

Total with taxes and fees

A spacious living area with a sofa, armchairs, a coffee table, and a dining area with a table and chairs.

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

Lenox

$284 nightly

Sep 23 - Sep 24

Total with taxes and fees

A flat landscape with a clear sky and distant hills.

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

Richmond

$646 nightly

Sep 28 - Sep 29

Total with taxes and fees

A two-story house with a front porch, surrounded by a garden with various plants and rocks.

10. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Stockbridge

Anonymous traveler

$766 nightly

Sep 28 - Sep 29

Total with taxes and fees

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

11. Stylish Mid-century Modern Berkshires Cape

Lee

H B.

$782 nightly

Oct 18 - Oct 19

Total with taxes and fees

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

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

Great Barrington

Mark M.

$656 nightly

Sep 23 - Sep 24

Total with taxes and fees

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

13. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Ann C.

$476 nightly

Oct 13 - Oct 14

Total with taxes and fees

A garden area with potted plants, a wooden fence, and outdoor furniture.

14. 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.

$175 nightly

Sep 23 - Sep 24

Total with taxes and fees

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

15. Vacation Village in the Berkshires

Williamstown

Jacob

$122 nightly

Sep 23 - Sep 24

Total with taxes and fees

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

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

Sherwood Forest

William C B.

$257 nightly

Sep 27 - Sep 28

Total with taxes and fees

A hot tub with a string of lights above it, set against a dark night sky.

17. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Sherwood Forest

Frank M.

$352 nightly

Sep 29 - Sep 30

Total with taxes and fees

A snow-covered outdoor area with a fire pit, tables, and chairs.

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

Hancock

Maura D.

$190 nightly

Sep 23 - Sep 24

Total with taxes and fees

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

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

New Lebanon

Varun M.

$203 nightly

Sep 23 - Sep 24

Total with taxes and fees

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

20. Micosta Leisure Inn

Hudson

Kim

$118 nightly

Oct 5 - Oct 6

Total with taxes and fees

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Top Lee Hotel Reviews

Gateway to the Berkshires - Renovated downtown apartment

10/10 Excellent

"Upon entry we noted how clean and orderly the apartment was. It was Founders Day weekend so the location was excellent as it is right in the middle of the action and didnt require driving and/or having to pray for a parking spot. We would most definitely stay there again. Communication with Emmy was quick and she always had an answer for any stupid question I had for her. Well worth it for us."

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."

Chambery Inn

8/10 Good

"This is a charming little inn. We enjoyed a cozy suite with a fireplace and a hot tub. The bed was very comfortable and the doorside delivery of hot coffee and a continental breakfast in a cute picnic basket was a nice touch. Although the room was at the basement level (with small windows at the top of the ceiling), the fireplace added nice ambiance. The bathroom soaps and shampoo were a bit basic, but absolutely serviceable. And while we never met the innkeepers, they had left the keys and a useful packet of information for us when we arrived. This was a nice location for our two day stay to experience music at Tanglewood. I would stay here again."

Find out more about Lee

Everything you need to know about Lee vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Lee vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Lee vacation 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 low season months. For more hustle and bustle, you may prefer to visit Lee in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $577 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Lee rentals

At Expedia, we put the best Lee vacation 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 vacation.

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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Things to do in Western Massachusetts

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 Berkshire Mountain Country Store and Lee Premium Outlets.

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.

Lee Vacation Rentals

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Check prices for these dates

Our top choices for Lee vacation rentals

1. Berkshire Mountain Lodge

2. Riverside Retreat in the Berkshires

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

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

5. Treetop Hideaway in Tyringham

6. Home in Great Barrington

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

10. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

11. Stylish Mid-century Modern Berkshires Cape

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

13. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

14. Cozy Camper tucked into the woods

15. Vacation Village in the Berkshires

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

17. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

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

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

20. Micosta Leisure Inn

Find vacation rentals that suit your style

Top Lee Hotel Reviews

Gateway to the Berkshires - Renovated downtown apartment

Find out more about Lee

Explore a world of travel with Expedia

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