Lee Vacation Rentals from AED 280: 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.

A historic street with brick buildings, storefronts, and parked cars.

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Our top choices for Lee vacation rentals

1. Berkshire Mountain Lodge

Pittsfield

Susan J

AED 397 total

includes taxes & fees

6 Dec - 7 Dec

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

2. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

AED 2,116 total

includes taxes & fees

13 Nov - 14 Nov

A dining area with a wooden table, chairs, and a ceiling fan.

3. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

AED 1,052 total

includes taxes & fees

13 Nov - 14 Nov

A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

4. Secluded Family Home in Serene Stockbridge Woods

Stockbridge

Ofer C.

AED 2,187 total

includes taxes & fees

16 Nov - 17 Nov

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

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

Great Barrington

bob i.

AED 425 total

includes taxes & fees

18 Nov - 19 Nov

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

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

Stockbridge

Anonymous traveler

AED 3,028 total

includes taxes & fees

7 Dec - 8 Dec

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

7. Home in Great Barrington

Great Barrington

Janet G.

AED 1,112 total

includes taxes & fees

13 Dec - 14 Dec

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.

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

Sherwood Forest

Brian C.

AED 1,312 total

includes taxes & fees

15 Nov - 16 Nov

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

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

Great Barrington

Kristin O.

AED 1,194 total

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with a dining area, built-in shelves, and a large window.

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

Lenox

AED 1,063 total

includes taxes & fees

14 Nov - 15 Nov

A modern living room with grey sofas, a wooden coffee table, a stone fireplace, and a kitchen in the background.

11. Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

Great Barrington

AED 1,350 total

includes taxes & fees

20 Nov - 21 Nov

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

12. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Stephen L.

AED 1,736 total

includes taxes & fees

14 Nov - 15 Nov

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

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

Great Barrington

Mary R.

AED 2,449 total

includes taxes & fees

16 Nov - 17 Nov

A wooden fence, a potted plant, a wooden bench, and a small garden area with a stone pathway.

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.

AED 640 total

includes taxes & fees

13 Nov - 14 Nov

15. Vacation Village in the Berkshires

Williamstown

Carol

AED 370 total

includes taxes & fees

15 Nov - 16 Nov

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

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

Sherwood Forest

Frank M.

AED 1,375 total

includes taxes & fees

13 Nov - 14 Nov

A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

17. Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic

Eric H.

AED 1,063 total

includes taxes & fees

13 Nov - 14 Nov

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

18. Micosta Leisure Inn

Hudson

George

AED 327 total

includes taxes & fees

16 Nov - 17 Nov

A lakeside picnic area with a bench and umbrella, surrounded by autumn-colored trees.

19. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Hinsdale

Kyle R.

AED 1,605 total

includes taxes & fees

15 Nov - 16 Nov

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

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

Sherwood Forest

William C B.

AED 1,042 total

includes taxes & fees

26 Nov - 27 Nov

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Find vacation rentals that suit your style

Top Lee Hotel Reviews

A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

Devonfield Inn B&B

Lee

10/10 Excellent

Anonymous traveler

A bedroom with a large mural of a waterfall, two bedside lamps, a bed with multiple pillows, and a nightstand with a lamp.

Changing Times Boutique Country Lodging

Craryville

10/10 Excellent

Our second time staying here was even more lovely than the first! We brought more family members after our great experience last year. We love the easy check in, cozy comfortable rooms, lots of extras (books and DVDs in the hallway, sweet treats downstairs and in the rooms) and Loretta is the BEST host! She makes an exquisite breakfast and accommodates our early start time. Can’t wait to stay here again.

Kathleen

A spacious living room with high ceilings, exposed wooden beams, a fireplace, and comfortable seating.

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

Michelle

A two-story building with a sign reading "Chambéry Inn".

Chambery Inn

Lee

10/10 Excellent

Elaine

Wilder House Berkshires

Sheffield

10/10 Excellent

Liliana

The Inn at Stockbridge

Stockbridge

10/10 Excellent

Kevin

A large, two-story house with a porch and multiple windows, surrounded by a well-maintained lawn.

The White Hart

Salisbury

10/10 Excellent

We enjoyed our stay at the White Hart. We got a room in the back of the building overlooking a garden. We loved sitting out there and relaxing. The room was a nice size and comfortable. The complementary breakfast provided a good selection and was tasty. The lobby is a nice place to have coffee or wine. The chairs are everywhere and make it a nice place to relax. Service was friendly and attentive and Provisions provides excellent sandwiches. We were also able to park right outside our...

thomas

A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

Brook Farm Inn

Lenox

10/10 Excellent

roberta

A building entrance with a large planter with purple flowers and a small tree.

Hotel On North

Pittsfield

10/10 Excellent

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

A large, two-story house with a front porch and a well-maintained garden with various flowers and shrubs.

Harbour House Inn

Cheshire

10/10 Excellent

Anonymous traveler

Shaker Mill Inn

West Stockbridge

10/10 Excellent

This was the most comfortable B&B I have every heard of let alone stayed at. It does not have the awkwardness of eating breakfast in a community room of strangers. All the breakfast amenities are in you room, including the food that is stock daily by the inn keepers, so you get to enjoy in the comforts of your room (which is a cozy as home). The room was so spacious and well kept. Every detail is thought of by the innkeepers and if they forgot something they are accessible and gracious to...

Joe

A snow-covered outdoor area with a patio, seating, and a covered dining area.

The Cornell Inn, Lenox & The Berkshires

Lenox

10/10 Excellent

Lawrence

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

10/10 Excellent

We were greeted by extremely friendly staff. Check in and check out was seamless. Room was very nice and immaculate. We especially liked the bathroom design - didn't have to trip over the toilet to get in the shower as in most hotels! Free breakfast was the usual fare, but in a very pleasant and uncrowded room. Appreciated the free US News and NY Times Beautiful indoor pool - wish we'd brought our bathing suits!

Anonymous traveler

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.

Lee Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Lee vacation rentals

1. Berkshire Mountain Lodge

2. Sun Filled Lenox Retreat - Minutes to Tanglewood!

3. Leaf-Peeper Paradise in the Berkshires

4. Secluded Family Home in Serene Stockbridge Woods

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

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

7. Home in Great Barrington

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

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

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

11. Luxe Berkshires Ski Retreat w/ Fireplace, King Bed, Chef's Kitchen, Washer/Dryer

12. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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

14. Cozy Camper tucked into the woods

15. Vacation Village in the Berkshires

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

17. Sweet Cozy Victorian in Housatonic. Close to everything.

18. Micosta Leisure Inn

19. Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

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

Find vacation rentals that suit your style

Top Lee Hotel Reviews

Devonfield Inn B&B

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in Lee?

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

How many vacation rentals are there in Lee?

What can I see and do in Lee?

What are vacation rentals like in Lee?