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

Lee Vacation 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.

Dates

November 2026

December 2026

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Our top choices for Lee vacation rentals

1. Berkshire Mountain Lodge

Pittsfield

Charline

$107 nightly

Dec 8 - Dec 9

Total with taxes and fees

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

2. Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

Patricia O.

$523 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

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

Stockbridge

Anonymous traveler

$718 nightly

Dec 1 - Dec 2

Total with taxes and fees

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.

$534 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

5. Leaf-Peeper Paradise in the Berkshires

Great Barrington

Kelly B.

$262 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

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

Great Barrington

Kristin O.

$263 nightly

Nov 8 - Nov 9

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.

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

Sherwood Forest

Brian C.

$311 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

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

Great Barrington

bob i.

$102 nightly

Nov 14 - Nov 15

Total with taxes and fees

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

9. Home in Great Barrington

Great Barrington

Janet G.

$281 nightly

Nov 9 - Nov 10

Total with taxes and fees

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

$264 nightly

Nov 10 - Nov 11

Total with taxes and fees

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

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

Great Barrington

Mary R.

$581 nightly

Nov 16 - Nov 17

Total with taxes and fees

A covered outdoor area with a brick floor, wooden furniture, and a fireplace.

12. Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington

Great Barrington

$1,206 nightly

Nov 9 - Nov 10

Total with taxes and fees

A residential area with houses, a driveway, and a body of water in the background.

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

Pittsfield

Stephen L.

$409 nightly

Nov 9 - Nov 10

Total with taxes and fees

14. Vacation Village in the Berkshires

Williamstown

Marcos

$122 nightly

Dec 8 - Dec 9

Total with taxes and fees

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

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

Housatonic

Eric H.

$257 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

16. Micosta Leisure Inn

Hudson

George

$113 nightly

Nov 9 - Nov 10

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.

$326 nightly

Nov 8 - Nov 9

Total with taxes and fees

A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

18. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

Dalton

Marcia O.

$262 nightly

Nov 10 - Nov 11

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.

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

Sherwood Forest

William C B.

$250 nightly

Nov 12 - Nov 13

Total with taxes and fees

A modern living room with a sectional sofa, wooden beams, a large window, and a view of the outdoors.

20. Beautiful and Private Home Centrally Located in the Berkshires

West Stockbridge

$1,147 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

Chambery Inn

Lee

10/10 Excellent

Elaine

The Inn at Stockbridge

Stockbridge

10/10 Excellent

Kevin

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 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 lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee

10/10 Excellent

Sheila

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

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 tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

South Lee

10/10 Excellent

I love this place and have stayed here before. Even with the precautions for COVID-19, my kids and I still had a great time. The check-in was smooth and safe. The room was clean and sanitized. In fact, we had to "break the seal" on the door to enter and the seal was evidence of the cleaning that was done. Of course, the arcade and movie theatre were closed, but that was no surprise. The pools were open and reservations required to ensure everyone could be safe and still have fun. Lots of...

David

Two Adirondack chairs facing a river with a forested hill in the background.

The Yankee Inn

Lenox

10/10 Excellent

We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!

Colleen

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

Courtyard by Marriott Lenox Berkshires

Lenox

10/10 Excellent

Alyssa

A two-story house with a brick entrance and a white facade.

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

Stockbridge

10/10 Excellent

Charles

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 $113 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.

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

Bundle & Save

OneKeyCash

Upfront pricing

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

4. Secluded Family Home in Serene Stockbridge Woods

5. Leaf-Peeper Paradise in the Berkshires

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

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

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

9. Home in Great Barrington

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

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

12. Maya's Garden House: A Converted 3-Bedroom Barndominium on 32 Acres in Great Barrington

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

14. Vacation Village in the Berkshires

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

16. Micosta Leisure Inn

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

18. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

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

20. Beautiful and Private Home Centrally Located in the Berkshires

Find vacation rentals that suit your style

Top Lee Hotel Reviews

Devonfield Inn B&B

10/10 Excellent

Find out more about Lee

Everything you need to know about Lee vacation rentals

Lee vacation rentals: An excellent choice for every season

How to find incredible deals on Lee rentals

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?

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