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.
Apartment in Pownal
5 out of 5 average rating, 8 reviews"The Triple Chambers"
This beautiful, spacious, and historic property was formerly the Inn at Oak Hill. It is convenient to Williams College, Williamstown Theater Festival, Clark Art Museum, MassMOCA, FreshGrass Festival, BerkshireStock, Jiminy Peak, Bennington College, VAST snowmobile trails, and many other destinations in southern Vermont and western Massachusetts. Comfortably furnished with modern amenities such as Wi-Fi and satellite TV, our home also surrounds you with beautifully preserved & original features.
Home in Pittsfield
4.97 out of 5 average rating, 111 reviewsBerkshire Lake- Modern and Updated-close to skiing
Lakefront Home for Rent. This home has been 100% remodelled! With a beautiful spot directly on Pontoosuc, the new kitchen, bathrooms, fireplace, and glass enclosed family room all benefit from the idyllic scenery. The home has 5 bedrooms and a convertible playroom with a futon for even more space. 2 bedrooms have bunk beds plus a full size bed in them. 2 bedrooms have king size beds and 1 has a queen. The master suite has an en-suite bathroom and a balcony overlooking the lake. Many upgrades!
Apartment in Copake Falls
4.91 out of 5 average rating, 309 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!
Home in Old Chatham
4.96 out of 5 average rating, 24 reviewsPost and Beam Hilltop Sanctuary
Enjoy the quiet countryside/mountain views from this breathtaking private hilltop getaway. Step into our stunning vaulted Post & Beam home with central fireplace, cozy loft and spacious open floor plan that features a full wall of windows/doors to the back wrap around deck that allows for an incredible indoor/outdoor living experience with friends and family. Take advantage of our fully stocked chefs kitchen, comfy beds complete with fresh linens/towels and each bedroom has its own full bath.
Home in Great Barrington
4.88 out of 5 average rating, 101 reviewsGreat Barrington, Cabin Sleeps 14, Walk To Town
You and your family cannot beat this PRIME location in downtown Great Barrington while still feeling remote and in the rolling hills of The Berkshires. Quick 20 minute drive to Tanglewood, 5 minutes to Ski Butternut, 15 minutes to Catamount Ski Mountain, 350 feet walking distance to all the great restaurants and shops of downtown Great Barrington and plenty more! Short walk to a great lake with a beach area - bring your dogs and family to swim in or walk around and enjoy the nature reservation!
Home in Great Barrington
4.95 out of 5 average rating, 20 reviewsLuxury Redo: Hot Tub, Playroom, Sleeps 12
Creamery: Fully Renovated 5 Bedroom Home, sleeps 12 with large screened porch, outdoor patio with seating, sun umbrella, hot tub, fire pit and billiards! Amenities also include: Central AC, all new kitchen appliances, washer/dryer, 4 Smart tvs, fiber internet + good cell service, propane fireplace, blue stone outdoor patio with seating, billiards table, playroom, high quality linens included, Front porch with seating, superior central location: less than 10 to GB, less than 10 to Catamount!
Home in Athens
4.93 out of 5 average rating, 114 reviewsLake house, 700 ft waterfront - from every room
Panoramic views from the wrap-around deck offers privacy and 700 feet of lake frontage from this comfortable home. Enjoy the sunrise and sunsets views of the lake from EVERY room. Two kayaks, canoe, paddle board to be enjoyed from its private beach. The great room has full lake view, heated floors and two large decks. This home offers 4 bedrooms, 2 and 1/2 baths, a finished lower level that features game room with private deck, ping pong table, giant Jenga, home gym, and large 55in TV.
Cottage in Great Barrington
4.83 out of 5 average rating, 35 reviewsTHE GREAT ESCAPE BERKSHIRE SKI COTTAGE w/HOT TUB!
It's all about the location and the interior renovation that makes our cottage stands out. Only 5 min to Catamount Ski Mountain, 10 min from Butternut and Only 5 min from town of Great Barrington with dining experience, Bowling ally, movie theater. Summer - for swim and boating - 5 min from Mansfield (swim) and 20 min to stockbridge bowl (boating). 5bd, 4 bath, 2 living rooms, fire place, Hot tub, fire pit, nesting on a 5 acre wooded forest, for complete privacy. (back yard is fenced) .
Villa in Pownal
4.94 out of 5 average rating, 65 reviewsVermont Vacation Villa—Grapevine Getaway
Nestled in the stunning natural beauty of Vermont, this striking villa offers the perfect escape from the hustle and bustle of everyday life. Surrounded by rolling hills, and picturesque countryside, this home is a paradise. Whether exploring the area's cultural institutions, immersing yourself in the natural beauty of Vermont, or relaxing and unwinding with family and friends, this vacation home is the perfect retreat. Experience the magic of this beautiful area for yourself!
Home in Sheffield
4.9 out of 5 average rating, 115 reviewsWow! Best BERKSHIRE SnowHome #1 Private SuperClean
"238 Main" has two rentals. Rental #1 has 2 bedrooms, a FULLY EQUIPPED KITCHEN and it is SUPERCLEAN! (ALSO SEE THE 1 BEDROOM LISTING #2!) We are conveniently located in between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. Two Queen size beds. High Speed WiFi. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!
Home in Hudson
4.94 out of 5 average rating, 16 reviewsKees Cottage
The best of all worlds! Beautifully remodeled 1910 farmhouse is mostly furnished with one-of-a-kind antiques, giving it a rustic, yet upscale vibe. Our large yard is magically peaceful and quiet, with a delightful hidden path leading to the pool and pool house. Amidst all this peace and privacy, you are still just 5 min. from the town of Hudson, with all of its boutiques, eateries, and culture. We offer 3 bedrooms and 1.5 baths, accommodating 6 guests.
Apartment in Williamstown
5 out of 5 average rating, 118 reviewsDowntown | Waterfront | Walk to Shops
★ New to Williamstown? Explore our interactive guidebook. One bedroom with all the bells and whistles! Meticulously upgraded with the discerning guest's convenience in mind. The property is in the midst of Williamstown's popular spots: Williams College campus, theaters, museums, restaurants, shops, and golf course. It also sits by the rushing, sometimes tranquil, Green River where you can sit back, relax and enjoy the fire pit.
Vacation rentals for every style
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Popular amenities for Lenox vacation rentals
Other great vacation rentals in Lenox
Home in Athens
5 out of 5 average rating, 36 reviewsPerfect home for a getaway from NYC
Home in Hillsdale
5 out of 5 average rating, 52 reviewsLakefront close to ski & shopping
Home in Granby
5 out of 5 average rating, 6 reviewsLake house retreat Granby CT
Home in Millerton
4.96 out of 5 average rating, 168 reviewsVacation Home In Millerton
Home in Charlemont
4.94 out of 5 average rating, 53 reviewsTall Pines Rental
Home in Monroe
4.92 out of 5 average rating, 12 reviewsThe Camp
Home in Athens
4.9 out of 5 average rating, 10 reviewsCozy Catskill Getaway by Hudson
Home in Averill Park
4.96 out of 5 average rating, 156 reviewsCozy, peaceful lake house close to Jiminy Peak
Quick stats about vacation rentals in Lenox
Total rentals
240 properties
Nightly prices starting at
G$2,089 GYD before taxes and fees
Total number of reviews
7.9K 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 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 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.
How much does it cost to stay in bed and breakfast rentals in Lenox?
Experience the best of Lenox with our bed and breakfast rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget 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 bed and breakfast rentals in Lenox have wifi?
Absolutely! We offer over 10 bed and breakfast 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.
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.
Do cabin rentals in Lenox have a bbq area?
Absolutely! We offer over 10 cabin rentals with a bbq area in Lenox. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly apartment rentals in Lenox?
Lenox has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Bed And Breakfast Rentals in Lenox?
Enhance your stay in our Bed And Breakfast Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
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