Vacation rentals in Lee

4.94 out of 5 average rating, 416 reviews

An expansive deck is surrounded by lush greenery, featuring outdoor seating and a dining area. Warm café lights hang overhead, creating a cozy atmosphere. A person is seen grilling at a gas grill, while another enjoys a meal at a table, capturing a serene outdoor experience.

Chalet in Otis

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

4.99 out of 5 average rating, 294 reviews

A whimsical structure features a unique tree integrated into its design, with wooden shingles and a peaked roof. Sturdy stairs lead to the entrance, surrounded by lush greenery. Large windows provide glimpses of the enchanting architecture, enhancing the magical ambiance of the setting.

Treehouse in Tyringham

Gingerbread House Tower in the Berkshire Hills

Escape to this newly renovated, off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. If looking for activity, guests can spend the day on the grounds, walking nearby trails, or exploring the many nearby Berkshire towns.

An outdoor seating area is arranged under a wooden pergola adorned with string lights. Comfortable chairs surround a central fire table, which is equipped for warmth and ambiance. Lush greenery and a picnic table are visible in the background, contributing to the serene outdoor setting.

4.97 out of 5 average rating, 211 reviews

Berkshire 4 season home

The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.

Apartment in Great Barrington

An entrance is framed by a dark door, which is ajar. Light spills into the entryway, highlighting a visible seating area with a gray couch beyond. A contemporary light fixture illuminates the wall beside the door, enhancing the overall welcoming feel.

4.88 out of 5 average rating, 104 reviews

Kitchenette|King Bed|Couch

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. *1.5 miles to Downtown *1.3 miles to Mahaiwe Performing Arts Center *44 miles to Albany International Airport *4.5 miles to Great Barrington Airport *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *58"Tv with Hulu Live

Guesthouse in Great Barrington

A well-lit hallway is shown, leading towards a staircase with polished wooden steps and a black handrail. A decorative rug is positioned at the entrance, and doors are visible along the walls, adding a sense of depth to the space.

4.96 out of 5 average rating, 124 reviews

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

4.99 out of 5 average rating, 285 reviews

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relax by the firepit- we hope you enjoy your stay and will visit us again.

Superhost

A lively main street showcases a mix of historic brick buildings, adorned with American flags. Various cars and motorcycles navigate the road, highlighting local commerce. Outdoor seating and awnings are positioned along the sidewalks, creating an inviting atmosphere for pedestrians.

Guest suite in Lee

4.77 out of 5 average rating, 119 reviews

Cozy Guesthouse Near Downtown, Lee

Welcome and enjoy our renovated Guesthouse at Lee, MA, staying on main street (15 minutes from Great Barrington and 20 minutes from Pittsfield). It is also 3 mins to Outlet and 19 mins to the closest Ski area.The master bedroom has a queen size soft mattress, and the second bedroom has a queen bed also. The kitchen has a brand new refrigerator, a gas range, and units for cooking. You will enjoy the comfortable stay! Owners live upstairs and be friendly to all visits.

4.95 out of 5 average rating, 274 reviews

A calm lake reflects vibrant autumn foliage, with trees displaying shades of red, orange, and yellow. A boat is anchored near a wooden dock, and the surface of the water mirrors the colorful landscape, creating a serene and picturesque scene.

Cottage in Becket

Berkshires Cottage by Lake. Year Round Adventures.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX(will consider pets.)(90 second walk through wooded path to lake)

4.93 out of 5 average rating, 374 reviews

The exterior of the Granary is highlighted, featuring a mix of red barn siding and natural stone. The two upper windows allow natural light inside, while a mint green double door adds a pop of color. Lush greenery and colorful flowers surround the entrance.

Guesthouse in Lenox

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Guesthouse in Stockbridge

The kitchenette features modern black cabinetry, open wooden shelves, and a sleek countertop. A microwave and a compact oven are included, along with a sink below a skylight. Glassware, jars, and dishware are neatly arranged along the shelves, enhancing functionality and style.

4.95 out of 5 average rating, 234 reviews

Modern studio with views of the treetops

Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

4.91 out of 5 average rating, 123 reviews

A spacious bedroom features a large window with a view of the lush greenery outside. The bed is adorned with a mix of pillows and a colorful area rug rests on the floor, enhancing the room's serene atmosphere.

Cabin in Lee

Secluded Berkshire cabin with scenic views

The Beaver Dam is a sunlight-filled & recently renovated cabin tucked in the woods, overlooking the October Mountain State Park and steps away from Basin Pond. We are located close to a number of excellent ski slopes. Our cottage is the last house on a private road and right next to protected forest. You can't ask for more privacy, peace and quiet than you'll find at our little piece of paradise on the pond!

4.97 out of 5 average rating, 101 reviews

Stylish Mid-century Modern Berkshires Cape

Stylish and design forward, yet entirely comfortable for families and kids. Fully renovated 4 bedroom, 2.5 bath home located in the heart of the Berkshires. Enjoy the large, sunny yard and deck with lots of seating and a large dining table - perfect for al fresco dinner and drinks! The house is decorated in mid century modern style with gorgeous design touches throughout!

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Other great vacation rentals in Lee

Superhost

A spacious outdoor area is featured, surrounded by lush greenery and colorful landscaping. Multiple wooden chairs are arranged around a fire pit, with logs and nature providing a tranquil setting for relaxation. A picturesque view of rolling hills can be seen in the background.

4.89 out of 5 average rating, 19 reviews

Centrally Located Historical Home

AdaRating, 5 stars9 months ago

We stayed for three nights at this beautiful house. It is ideal for two adult couples with two bedrooms and two bathrooms, both bedrooms have queen size beds. The bedrooms are upstairs, and there is a powder room on the first floor. The house is very clean, fully equipped kitchen, nice view from the open porch. It is on a quiet street, but very close to the center of the town. Tanglewood is 13 min drive, many major Berkshire attractions are a short drive away. Lucas is very prompt in responding to any questions, all check in/check out instructions were clear. We enjoyed our stay a lot!

4.96 out of 5 average rating, 78 reviews

A charming two-story building is nestled in a snowy landscape, surrounded by tall trees covered in frost. Soft light glows from the windows, and a path leads to the entrance, highlighting the tranquil winter setting.

Guesthouse in Pittsfield

The Nest at Birdland

MichelleRating, 5 starstoday

The Nest was a great spot for us to rest and recoup before our NEYC day! Mary was easy to work with, communicated well, and provided a great space with so many thoughtful extras!

A bright sleeping area features two beds with neutral bedding, complemented by a small sofa and a coffee table. Natural light enters through multiple windows, while a standing lamp and nightstand provide additional lighting. A mirror enhances the sense of space, and a closet is visible.

Apartment in Lee

4.77 out of 5 average rating, 119 reviews

Cozy Berkshire Cottage Style Apartment

JesseRating, 5 stars7 months ago

Loved Bettina's place! It was cozy and comfortable and very well located for a fun weekend all around the Berkshires. The place was generally well appointed and took care of all my needs. Definitely recommended!

4.97 out of 5 average rating, 67 reviews

A compact laundry area features a stacked washer and dryer in sleek stainless steel, positioned near a door that leads outside. Natural light filters through the glass panes of the door, creating a bright and functional space.

Apartment in Lenox

Main Street Delight - One Bedroom Apartment

NoraRating, 5 stars1 week ago

This couldn't be a more perfect location. Walkable to everything and centrally located. The apartment itself was beautiful as well.

Two small dogs are seen resting on a lush green lawn. One dog lies comfortably under a vibrant orange Adirondack chair, while the other stands nearby, creating a relaxed and welcoming outdoor atmosphere.

Apartment in Lee

4.66 out of 5 average rating, 118 reviews

Upstairs on Main

DanielRating, 5 stars1 week ago

Jeff was very hospitable the place was clean and homey and we loved the small town feel of Lee

An outdoor seating area features two Adirondack chairs positioned around a fire pit, surrounded by grassy land. Stumps serve as natural seating. A meadow and trees create a serene backdrop, while cloudy skies contribute to the tranquil atmosphere.

5 out of 5 average rating, 8 reviews

Meadowbrook Cottage

JoshRating, 5 stars4 weeks ago

Had a wonderful experience staying at Brian and Deb’s house - a perfect weekend getaway. The house itself was great to stay in - it’s well-maintained, cozy, and orderly. The location was great too - near towns and hikes, but tucked away on a very peaceful property. Would definitely recommend!

4.98 out of 5 average rating, 49 reviews

A spacious kitchen features a white color scheme with marble flooring. A central wooden island offers seating for two, while stainless steel appliances are visible. Black cookware hangs on the wall, and natural light flows in through a nearby window.

Apartment in Stockbridge

Stockbridge private apartment

CatherineRating, 5 stars2 weeks ago

This was a great weekend getaway for two of us. The apartment is pristine and private. It was a great base camp for outings in the Berkshires. Stockbridge is just one mile away up the road and has tons of cute shops and restaurants.