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Vacation rentals in Lee

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Top-rated vacation rentals in Lee

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Home in Lee

4.9 out of 5 average rating, 223 reviews

1817 Berkshire Farmhouse- Close to Everything.

*Close to ski resorts & tubing! We are nestled at the foot of October Mountain State Forest, yet close to the centers of Lee, Lenox, & Pittsfield. Our charming house was built in 1817- original wood beams, wood floors, and quite a history. Whether you enjoy skiing, exploring local restaurants & downtowns, venturing outdoors or experiencing the local art scene, the Berkshires has something for everyone. Our little farmhouse serves as the perfect "home base" for all of your Berkshire adventures.

Chalet in Otis

4.94 out of 5 average rating, 376 reviews

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

Home in Lee

4.9 out of 5 average rating, 250 reviews

Cozy Berkshires Cottage

Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)

Treehouse in Tyringham

5 out of 5 average rating, 262 reviews

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.

Rental unit in Lee

4.77 out of 5 average rating, 118 reviews

Cozy Berkshire Cottage Style Apartment

Stay in a cozy Berkshires apartment! All new windows allow views to the peaceful surrounding state forest and yard. Watch humming birds, oriols, deer, squirrels, opossums, racoons, woodchucks, and more... The house is set back from the road, easily accessible, yet private. The cottage is a duplex: the Airbnb apartment is on the left side of the cottage. • Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Stockbridge, Lenox, MA Turnpike • Ideal for lovers of nature & the Berkshires

Rental unit in Canaan

4.99 out of 5 average rating, 140 reviews

Mountain View Getaway

Come relax & enjoy panoramic mountain and pond views. Marvel at the dramatic lighting effects on Mercer Mt from sunrise-sunset from your private deck or bright living room. Fully equipped kitchen, grill on the deck, short scenic drive to a wide variety of restaurants & endless cultural venues in the surrounding quaint villages of Berkshire County Mass and Columbia County NY. Near hiking trails, skiing, apple picking & farm stores. Queechy Lake swimming, NYS boat launch for car top boats.

Guest suite in South Lee

4.92 out of 5 average rating, 201 reviews

Sunny Riverside Apartment

The Berkshires are a perfect spot for a getaway week or weekend. You will enjoy this cozy 2-story apartment, easily accessible to all that the region has to offer. The apartment has a fully equipped kitchen, dining space, living area, and two bedrooms, overlooking the Housatonic River. Every town in South County is 5-15 minutes drive, and in 50 minutes you could be at The Clark Museum or Mass MOCA in North County. Several ski areas are nearby, and Kripalu is just an easy 10 minute drive.

Farm stay in Pittsfield

4.99 out of 5 average rating, 160 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

Guesthouse in Lenox

4.94 out of 5 average rating, 335 reviews

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

4.95 out of 5 average rating, 207 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.

Cabin in Lee

4.91 out of 5 average rating, 116 reviews

Cabin with views in the Berkshires!

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!

Rental unit in Lenox

4.88 out of 5 average rating, 186 reviews

Station House 1E Private Room & Bath

Our place is a central location in Berkshire County, short drive to restaurants and shops; art and culture, skiing and hiking also close by. You’ll love this former train station( next to the Housatonic RR tracks) which is on three acres between a chapel, the scenic Housatonic River and October Mountain. Our place is good for couples, solo adventurers, and business travelers.

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Popular amenities for Lee vacation rentals

Free parking on premises

Air conditioning

Stay near Lee's top sights

The Mount, Edith Wharton's Home167 locals recommend

Lee Premium Outlets155 locals recommend

Shakespeare & Company134 locals recommend

Big Y World Class Market99 locals recommend

Haven67 locals recommend

Kennedy Park66 locals recommend

Other great vacation rentals in Lee

Cottage in Lee

4.99 out of 5 average rating, 99 reviews

Charming Renovated Berkshire Home

Home in Lee

4.83 out of 5 average rating, 29 reviews

Cozy and restful getaway in Lee

Guesthouse in Stockbridge

4.87 out of 5 average rating, 15 reviews

Light-filled Carpenter's Cottage in Stockbridge

Rental unit in Pittsfield

4.81 out of 5 average rating, 80 reviews

The Sunset Sanctuary - King Bed with Kitchen

Home in Lee

4.95 out of 5 average rating, 22 reviews

River Front Cottage

Hotel room in Lee

4.89 out of 5 average rating, 18 reviews

Great Place |2 BD|Kitchen| Pool 

Rental unit in Pittsfield

5 out of 5 average rating, 23 reviews

Comfy Quaint Tavern

Guesthouse in Lee

4.89 out of 5 average rating, 65 reviews

The Justice's Birthplace - Modern Rustic Chic

Quick stats about vacation rentals in Lee

Total rentals
260 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
9.5K reviews
Family-friendly rentals
160 properties are a good fit for families
Pet-friendly rentals
60 properties allow pets
Rentals with a pool
70 properties have a pool

Frequently Asked Questions

Are there family-friendly vacation rentals in Lee?
Lee has more than 160 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Apartment Rentals in Lee?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with a gym, over 30 homes with wireless internet, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there pet-friendly vacation rentals in Lee?
Four-legged friends are welcome in Lee. Choose from more than 60 vacation rentals for guests traveling with pets.
Do apartment rentals in Lee have a gym?
Absolutely! We offer over 10 apartment rentals with a gym in Lee. Enjoy a tailored experience with all the comforts you desire.
Do boutique hotel rentals in Lee have air conditioning?
Absolutely! We offer over 20 boutique hotel rentals with air conditioning in Lee. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in guesthouse rentals in Lee?
Experience the best of Lee with our guesthouse rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Lee?
Yes! Work meets play with ease at over 120 vacation rentals in Lee featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do guesthouse rentals in Lee have wireless internet?
Absolutely! We offer over 10 guesthouse rentals with wireless internet in Lee. Enjoy a tailored experience with all the comforts you desire.
Are there Lee vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 70 vacation homes with pools in Lee, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Lee have a bbq area?
Absolutely! We offer over 50 house rentals with a bbq area in Lee. Enjoy a tailored experience with all the comforts you desire.

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