
Vacation rentals with outdoor seating in Lenox
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Top-rated outdoor seating rentals in Lenox
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Restored 1735 Granary I King Bed + Views & Pool
Restored 1735 granary on a peaceful Berkshires farmhouse compound. With 15-ft vaulted ceilings, original wide-plank floors, and mountain views, this design-forward retreat blends rustic charm with modern ease. Features a king bedroom, eat-in kitchen, and bathroom with soaking tub + standing shower. Centrally located in the Berkshires and just minutes to Lenox and Tanglewood. A quiet, light-filled space perfect for couples, creatives, and anyone seeking rest, reflection, and connection to nature.

The Old Red Barn
Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

Barn Stay at Shadowbrook Farm
Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

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!

The Writer's Cottage
The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and ironwork table.

The Berkshire Quintessential Cape downtown Lenox
Experience the best of the Berkshires in this charming, in-town, Lenox home! With stunning oak floors and white walls, this light-filled gem features high ceilings and abundant windows. Enjoy a cozy first-floor bedroom and full bath, while upstairs hosts two spacious bedrooms with a shared bath. The open-concept living and dining area, complete with a wood-burning fireplace, is perfect for gatherings. Just a short stroll to town, Tanglewood, and Canyon Ranch, this is your ideal getaway!

The Beer Diviner Brewery Apartment
The apartment is entire upstairs of back of our farm brewery & taproom. Open space includes living/dining/work space & bedroom; bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed (extra twin mattress beneath). HD TV, wifi, private deck, kitchenette with mini fridge, microwave, toaster oven, hot tea kettle and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

Granite Ledge, Modern home in a unique setting
Welcome to Great Barrington, the heartbeat of the Berkshires! This newly remodeled home that sits on 3.5 acres, is conveniently located 1 min from Butternutt Ski Mountain, and a 6 min drive from downtown main street Great Barrington. Convenient to restaurants, shops, farmers markets, art galleries, Tanglewood, Stockbridge, The Norman Rockwell Museum, Simon’s Rock, etc. Enjoy a vibrantly diverse restaurant scene and cultural events while still staying in a private setting.

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub
This newly-renovated historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 250 acre property.

Berkshire Mountain retreat with Urban eco-luxuries
600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relax by the firepit- we hope you enjoy your stay and will visit us again.

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.

Steps to MoCA: 2bd + SAUNA!
Enjoy peak autumn foliage in the Berkshires—now through early November! A spacious, private two-bedroom at the Small Mansion of Chase Hill Estate in North Adams. Just 3 minutes to MASS MoCA, 5 minutes to downtown restaurants, and 10 minutes to Williams College or The Clark. Whimsically restored (yes—fast Wi-Fi & great water pressure!) and part of @chasehillartistretreat. ✨ Your stay supports pro bono residencies for refugee & immigrant artists.
Popular amenities for Lenox outdoor seating rentals
House rentals with outdoor seating

Cozy Modern Sugar House with spectacular views.

Belle Meade

Charming Gem in Heart of the Berkshires

Private Home in The Berkshires (New Hot Tub!)

Cantabile life in the Berkshires

Sun-filled, Charming Stockbridge Classic- In Town!

Chic Hudson Farmhouse w/ Fireplace & Porch

Cheerful Catskill Village Cottage
Apartment rentals with outdoor seating

Beautfiul, modern, GB apartment

Sunny, light filled loft in 1873 Colonial

Beautiful space in the heart of Philmont

Bennett Abode

Sunny carriage house apartment

Mountain View Retreat~Sunny Hill Golf / Skiing

Hudson River Beach House

King Bed, Wi-Fi, 2m Ski Resort
Condo rentals with outdoor seating

Trailside At Hunter-Phase II-Hunter NY

Windham Condo

Mount Snow Ski Chalet

Spacious 3 bedroom apt in Lenox historic downtown

Winter Dream! The Handle Lodge at Snowtree Condos

Wyndham Bentley Brook

3 Story Condo - 5 Minutes to Mount Snow!

Historic house in 4 Corners area
When is the best time to visit Lenox?
Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
---|---|---|---|---|---|---|---|---|---|---|---|---|
Avg. price | R3,886 ZAR | R4,235 ZAR | R4,270 ZAR | R3,520 ZAR | R4,461 ZAR | R5,158 ZAR | R5,594 ZAR | R5,646 ZAR | R4,932 ZAR | R4,827 ZAR | R4,113 ZAR | R3,921 ZAR |
Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Quick stats about vacation rentals with outdoor seating in Lenox
Total vacation rentals
Explore 110 vacation rentals in Lenox
Nightly prices starting at
Lenox vacation rentals start at R1,046 ZAR per night before taxes and fees
Verified guest reviews
Over 5,080 verified reviews to help you choose
Family-friendly vacation rentals
70 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 20 rentals that welcome pets
Vacation rentals with a pool
10 properties feature pools
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Wi-Fi availability
110 of Lenox vacation rentals include wi-fi access
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Lenox rentals
4.8 Average rating
Lenox stays are highly rated by guests—averaging 4.8 out of 5!
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- Hunter Mountain
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Windham Mountain
- Bash Bish Falls State Park
- Kent Falls State Park
- Mount Greylock Ski Club
- Zoom Flume
- Catamount Mountain Ski Resort
- Norman Rockwell Museum
- Taconic State Park
- Wintonbury Hills Golf Course
- Hartford Golf Club
- Mount Tom State Reservation
- Bright Nights at Forest Park
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Opus 40
- Beartown State Forest
- Talcott Mountain State Park