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Lenox vacation rentals

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Top-rated vacation rentals in Lenox

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

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Home in Lee

4.9 out of 5 average rating, 226 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.

Home in Lee

4.9 out of 5 average rating, 253 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, 269 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.

Home in Stockbridge

4.95 out of 5 average rating, 110 reviews

Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

Cottage in Great Barrington

4.93 out of 5 average rating, 266 reviews

Artist Cottage

Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.

Home in Lenox

4.92 out of 5 average rating, 226 reviews

Heart of Lenox Walk to Town Cozy Cottage!

The cottage is a 2-minute walk to Church St., right in the heart of Lenox. Kennedy Park (1.5 miles) is a short stroll away for great hiking & biking, while multiple 5-star restaurants are all within a few minute walk. Tanglewood (2 miles), Kripalu (3 miles), Shakespeare & Co. (1 mile), Berkshire Theatre Festival & the Norman Rockwell Museum (7 miles), Butternut, Jiminy Peak (15 miles) & Bousquet (5 miles) ski area, Mahaiwe Performing Arts Center & Jacob's Pillow (14 miles) are all close by!

Rental unit in Canaan

4.99 out of 5 average rating, 147 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.

Home in Lenox

4.93 out of 5 average rating, 223 reviews

The Berkshire Quintessential Cape downtown Lenox

The quintessential Cape located on a quiet dead-end street in the center of Lenox. This completely renovated home has beautiful oak floors throughout. Decorators white painted walls with high ceilings & an abundant amount of windows allowing this well kept home to be flooded with beautiful light. First floor bedroom and full bath. Upstairs has two large bedrooms with shared bath. Open living and dining with wood burning fireplace. A quick stroll into town, Tanglewood & Canyon Ranch.

Home in Lenox

4.87 out of 5 average rating, 144 reviews

Spacious 4-Bedroom Colonial Gem in Downtown Lenox

Spacious 4-Bedroom Retreat in Lenox, MA Experience your perfect getaway in this beautifully renovated home in Lenox, MA. This charming 4-bedroom, 3-bathroom retreat offers 2,089 sq. ft. of space and is designed for a comfortable stay. The deck, BBQ grill, and cozy seating make for memorable gatherings. The Wi-Fi is fast for all your streaming needs, and there are 2 Wi-Fi HDTVs. Lenox, MA, is a picturesque town in the heart of the Berkshires. Book your stay today!

Farm stay in Pittsfield

4.99 out of 5 average rating, 170 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, 341 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, 213 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.

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Popular amenities for Lenox vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Lenox's top sights

Kripalu Center For Yoga & Health122 locals recommend

The Mount, Edith Wharton's Home167 locals recommend

Shakespeare & Company134 locals recommend

Bousquet Ski Area115 locals recommend

Haven67 locals recommend

Kennedy Park66 locals recommend

Other great vacation rentals in Lenox

Home in Lenox

5 out of 5 average rating, 24 reviews

Cliffwood Cottage

Rental unit in Lee

5 out of 5 average rating, 18 reviews

Cozy and comfortable apartment

Condo in Lenox

5 out of 5 average rating, 30 reviews

Spacious 3 bedroom apt in Lenox historic downtown

Home in Lenox

4.96 out of 5 average rating, 24 reviews

The Aviary

Home in Lenox

5 out of 5 average rating, 18 reviews

Sunny House in Downtown Lenox

Cabin in West Stockbridge

4.99 out of 5 average rating, 74 reviews

Modern Cabin near Tanglewood

Home in Lenox

5 out of 5 average rating, 18 reviews

Lakefront Retreat -Private Dock,creek,and Fire pit

Home in West Stockbridge

5 out of 5 average rating, 32 reviews

Beautiful And Private Home Centrally Located

Quick stats about vacation rentals in Lenox

Total rentals
230 properties
Nightly prices starting at
R181 ZAR before taxes and fees
Total number of reviews
7.4K reviews
Family-friendly rentals
110 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
40 properties have a pool

Frequently Asked Questions

Are there pet-friendly vacation rentals in Lenox?
Four-legged friends are welcome in Lenox. Choose from more than 50 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Lenox?
Yes! Work meets play with ease at over 110 vacation rentals in Lenox featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Lenox vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Lenox, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Lenox have a gym?
Absolutely! We offer over 10 house rentals with a gym in Lenox. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Lenox?
Lenox has more than 70 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Lenox have a bbq area?
Absolutely! We offer over 40 house rentals with a bbq area in Lenox. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Lenox?
Experience the best of Lenox with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do hotel rentals in Lenox have wifi?
Absolutely! We offer over 40 hotel rentals with wifi in Lenox. Enjoy a tailored experience with all the comforts you desire.
Do bed and breakfast rentals in Lenox have air conditioning?
Absolutely! We offer over 10 bed and breakfast rentals with air conditioning in Lenox. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Boutique Hotel Rentals in Lenox?
Enhance your stay in our Boutique Hotel Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

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