Lenox vacation rentals

5 out of 5 average rating, 10 reviews

Home in Wilmington

Lake & Mountain View Cabin - Sauna, Hot Tub, Hikes

Enjoy stunning lake & mountain views w/ easy access to hiking, swimming, boating, & fishing (kayaks, paddle board, and bikes included). Cathedral ceilings w/ beams provide a cozy feel & heated floors give an always-warm home in the winter. Covered deck w/ grill is great for outdoor dining. Additional features include outdoor hot tub, sauna, & quality game room (pool table, shuffleboard, foosball, ping pong). 4WD/AWD required in winter. Close to Mt. Snow & downtown Wilmington w/ shops and dining.

4.97 out of 5 average rating, 115 reviews

A spacious deck features several lounge chairs and a table, inviting relaxation. A bright red umbrella provides shade. The tranquil lake extends in the background, with a private dock visible along the shoreline, framed by lush greenery.

Home in Pittsfield

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!

4.96 out of 5 average rating, 25 reviews

A spacious living area features a central brick fireplace surrounded by built-in bookshelves. Light-colored sofas are arranged around a glass coffee table on a patterned rug, with large windows providing natural light and views of the outdoors.

Home in Old Chatham

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.

4.95 out of 5 average rating, 111 reviews

Home in Lake Katrine

Waterfront 3BR Home in Hudson Valley, Catskills

Key Residence Features at a glance; Waterfront on the Esopus Creek, Seasonal Kayaks, Rowboat, Dock (approx. Memorial Day weekend-mid October) large yard. Fully equipped kitchen, cable, wireless internet, washer and dryer. Enclosed porch, deck and patio with propane grill and patio furniture. Paved flat driveway, ramp allowing access to first floor, oversize door to first floor bathroom. Three spacious bedrooms with air conditioners. Convenient location close to thruway exits. No boat launch.

A wooden chair is positioned on a spacious deck, offering a view of the serene lake and surrounding greenery. A kayak is visible on the grass nearby, with the calm water reflecting the lush landscape.

4.93 out of 5 average rating, 117 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.

4.91 out of 5 average rating, 134 reviews

An open door leads to a private balcony, where a serene tree offers shade. A large, relaxed dog rests on the balcony floor. Bright greenery is visible, enhancing the tranquil outdoor atmosphere.

Apartment in Wilmington

Globetrotter Retreat too - Minutes to the Mountain

Newly renovated, fully furnished in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt on 2nd floor sleeps 4 people in comfort. Private balcony overlooks tranquil woods & rolling river. Steps to restaurants, bars & shopping. Supermarket is a short walk. Free Moover bus stop across the street ride for free to local destinations! 18 years or older guests only.

4.91 out of 5 average rating, 117 reviews

A well-lit bedroom features a black wooden bed with a plush blanket layered over crisp white linens. A small bedside table holds a lamp, and framed photos adorn the walls. A window with a blackout shade allows natural light while a wooden chair adds a touch of warmth.

Home in Sheffield

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Only one rental is rented at a time. Rental #1 has 2 bedrooms, FULLY EQUIPPED KITCHEN and is SUPERCLEAN! (SEE THE 1 BEDROOM LISTING #2!) We are conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. 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!

Superhost

Large glass doors provide a view of the surrounding woods and sunset, creating a bright and airy ambiance. A coffee table is positioned in front, accompanied by modern chairs and a dining table, enhancing the spacious and inviting feel of the living area.

Cabin in Rhinebeck

4.89 out of 5 average rating, 370 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

Superhost

Home in Readsboro

4.84 out of 5 average rating, 126 reviews

Beautiful Vermont! (Pet Friendly)

Country Home, nestled in the Green mountains, panoramic views, with access to the road. A babbling brook to lull you asleep from the master bedroom, a clawfoot soaking tub, stocked house. Hiking, antiques, shops, lakes, ski, snowboard, covered bridges, local inns, mountain views! Enjoy Vermont! Scenic roads, nearby Mt. Snow, VAST snowmobile trails, Mt.Greylock, Mass MOCA museum, N.Adams, MA, Berkshires. Bennington Wilmington. PEACEFUL & PERFECT Vermont getaway! ☺

4.91 out of 5 average rating, 209 reviews

An outdoor deck is featured, showcasing black wooden seating arranged around a spacious area. Expansive glass doors lead into the interior, allowing for natural light to fill the space. Lush greenery surrounds the cabin, enhancing the connection to nature.

Cabin in Catskill

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.

5 out of 5 average rating, 13 reviews

A serene outdoor deck features a centrally placed Solo Stove surrounded by five wooden Adirondack chairs. The scene captures a tranquil sunset with soft pink and orange hues reflecting off distant mountains and lush greenery.

Chalet in Craryville

Lockwood Lodge Mountaintop

Welcome to our slice of paradise in the Hudson Valley! Enjoy a secluded hilltop home with beautiful mountain and valley views, surrounded by 18 acres of woods. The open floor plan is perfect for cooking or relaxing in front of the fire, and enjoy grilling and the pool when the weather is right. The location is minutes from Hillsdale, and a 15-20 minute drive from Hudson and Great Barrington, with amazing restaurants and activities for every season.

Superhost

Apartment in Saugerties

5 out of 5 average rating, 3 reviews

Esopus Creekfront I Hot Tub I Fire Pit I Kayaks

Welcome to Upstate Waterfronts! Looking for a restorative Upstate getaway? This Creekside gem has you covered. - HOT TUB! - 3 bedrooms/ 1 full bathroom - Fully equipped kitchen & high-end amenities - Private creek access - including kayaks/vests/paddles - Stunning creek views - including a water facing balcony - 3,000 Arcade games, 75'' Smart TV, endless board games - High-speed WiFi - Prime location - walkable to town/restaurants/shops/beach

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Lenox vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Lenox's top sights

The Mount, Edith Wharton's Home167 locals recommend

Shakespeare & Company134 locals recommend

Haven67 locals recommend

Kennedy Park66 locals recommend

Alta53 locals recommend

Olivia's Overlook51 locals recommend

Other great vacation rentals in Lenox

5 out of 5 average rating, 38 reviews

Perfect home for a getaway from NYC

5 out of 5 average rating, 7 reviews

A wooden deck is visible, offering seating with blue rocking chairs. Lush greenery and a serene lake are seen in the background under a partially cloudy sky. The space invites relaxation and enjoyment of the natural surroundings.

Home in Granby

Lake house retreat Granby CT

4.97 out of 5 average rating, 177 reviews

An outdoor deck area is shown featuring several light-colored Adirondack chairs arranged around a stone fire pit. A neatly stacked pile of firewood is positioned against a backdrop of trees, creating a natural setting for relaxation and gatherings.

Home in Millerton

Vacation Home In Millerton

4.93 out of 5 average rating, 14 reviews

Home in Monroe

The Camp

5 out of 5 average rating, 57 reviews

Aerial view of a charming home nestled among vibrant autumn foliage, showcasing rich reds and yellows. Rolling hills and a serene green field extend in the background, while a quiet road meanders through the picturesque landscape.

Home in Whitingham

2.5mi from the lake! Fire pit, arcade, yard games!

5 out of 5 average rating, 13 reviews

Home in Great Barrington

Great Barrington Ranch. Sleeps 10,Hot Tub, 5 acres

A spacious outdoor deck features black lounge chairs set beside a low wooden table. A contemporary black chiminea stands as a focal point, surrounded by trees and open land, creating a relaxing atmosphere for outdoor gatherings.

5 out of 5 average rating, 16 reviews

Lake house with arcade games