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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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Condo in Hancock

4.93 out of 5 average rating, 71 reviews

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit1

Ski-in,ski-out! Unbeatable location for all seasons! Closest condo at JiminyPeak to the slopes and lifts. Located right at base of Mt. in JJ’sLodge in the heart of JiminyVillage. Mere steps to BerkshireExpress HighSpeed 6pack! Amazing pano views of the slopes surround. Designated pkg space in owner’s pkg lot. Unmatched access to all JP’s year-round activities. Skiing,MtBiking,hiking,tennis,swimming,fall foliage leaf peeping, shops,restaurants,MtAdventurePark w/ famous MtCoaster&AlpineSuperSlide.

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, 109 reviews

Berkshire 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

4.92 out of 5 average rating, 303 reviews

Modern 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 Great Barrington

4.95 out of 5 average rating, 20 reviews

Luxury 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 reviews

Lake 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 Red Hook

4.9 out of 5 average rating, 202 reviews

LAKE COTTAGE WITH HOT TUB - PAINTED TURTLE

Get away from it all to your little slice of paradise. Kayak, swim and rest. Just a hop skip and jump from the city. A blue stone pathways leads to your own private charming cottage overlooking a beautiful spring fed lake with your own private Hot Tub OPEN ALL YEAR ROUND and lake front oasis. Completely surrounded by perennials, and native trees. Lake dock, Hammock and kayaks await you. BE SURE TO SEE OUR OTHER 2 BEDROOM COTTAGE ON THE LAKE - LILY PAD - IF YOUR DATES ARE NOT AVAILABLE.

Cottage in Great Barrington

4.85 out of 5 average rating, 33 reviews

THE 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) .

Home in Sheffield

4.9 out of 5 average rating, 113 reviews

Wow! 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!) Fully renovated, large garden, private entrance, terrace and parking space. Two Queen size beds. High Speed WiFi. Berkshire Blend coffee/decaf, teas, milk, sugar and juice are a first morning welcome gift. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Villa in Pownal

4.93 out of 5 average rating, 60 reviews

Vermont 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 Hudson

4.93 out of 5 average rating, 15 reviews

Kees 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, 115 reviews

Downtown | 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.

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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 Athens

5 out of 5 average rating, 35 reviews

Perfect home for a getaway from NYC

Home in Hillsdale

5 out of 5 average rating, 50 reviews

Lakefront close to ski & shopping

Home in Charlemont

4.94 out of 5 average rating, 51 reviews

Tall Pines Rental

Home in Monroe

4.91 out of 5 average rating, 11 reviews

The Camp

Chalet in Athens

4.84 out of 5 average rating, 45 reviews

Large & Sunny Lakefront Home-kayaks/fire pit/games

Home in Lanesborough

5 out of 5 average rating, 13 reviews

Berkshire Mountain House

Home in Canaan

5 out of 5 average rating, 11 reviews

Luxury/pool/private Villa Mariana Blackberry River

Home in Averill Park

4.95 out of 5 average rating, 155 reviews

Cozy, peaceful lake house close to Jiminy Peak

Quick stats about vacation rentals in Lenox

Total rentals
230 properties
Nightly prices starting at
R183 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 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.
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.
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.
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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