Holiday rentals in Lenox

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Top-rated holiday rentals in Lenox

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

Guest favourite

Home in Pittsfield

4.97 out of 5 average rating, 111 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!

Guest favourite

Flat in Copake Falls

4.91 out of 5 average rating, 309 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!

Guest favourite

Home in Old Chatham

4.96 out of 5 average rating, 24 reviews

Post 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.

Superhost

Home in Great Barrington

4.88 out of 5 average rating, 101 reviews

Great 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!

Guest favourite

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!

Guest favourite

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.

Superhost

Cottage in Great Barrington

4.83 out of 5 average rating, 35 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) .

Guest favourite

Villa in Pownal

4.94 out of 5 average rating, 65 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!

Superhost

Cabin in Rhinebeck

4.89 out of 5 average rating, 357 reviews

Sunset Bungalow-Mt views on 130acre forest & falls

Newly renovated private cabin on the ridge top of an 130 acre magical property with stunning western views and overlooking a historic farm & crystal clear lake. Explore the hiking trails, dip in the wading pools of the upper cascades, bike to town or simply enjoy the peaceful sounds of the 90ft waterfall on the property. Relax in a beautifully designed private retreat, complete with a gourmet kitchen, cozy fireplace, and comfortable bedroom- learn more at cascadafarm.com

Guest favourite

Home in Sheffield

4.9 out of 5 average rating, 115 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!) 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!

Guest favourite

Cabin in Catskill

4.91 out of 5 average rating, 199 reviews

Modern & Cozy A-Frame 2BR + Loft, Firepit & Grill

Experience the beauty of the great outdoors while also enjoying modern comforts in this newly renovated A-frame cabin style home. This peaceful location away from the hustle and bustle is still easily accessible without a car and only a 10 minute taxi drive from the nearest station (Hudson Train Station) The elegantly finished interiors continue to be upgraded by the owners who love combining modern touches with the stunning natural surroundings of the area.

Guest favourite

Home in Hudson

4.94 out of 5 average rating, 16 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.