
Vacation rentals with outdoor seating in Lanesborough
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Top-rated outdoor seating rentals in Lanesborough
Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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.

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!

Net Zero home with rustic Berkshire charm
Be a part of the solution in our centrally located solar home that sits on a safe and quiet street just a walk, ride, or drive from downtown Pittsfield! Warm up your day on the screened-in sun porch. Warm up your toes on the heated tile floors! Enjoy custom concrete counters and wood floors in this open kitchen concept. Grill out on the rear patio while your dogs roam in the enclosed backyard. Hiking trails abound and playgrounds are just a stroll away. We are emissions free! How cool is that?!

Just Be Cabin
Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

In town, newly renovated studio with private deck
Come explore our unique area and stay in a renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

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 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.

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.

Wildlife Lakeside Cottage; views/wildlife
Fully furnished and remodeled with new upgrades in Spring 2025 including a cathedral master bedroom suite with a full bath. Our private cottage is set on a peninsula at a cove where a trout stream enters the lake. Incredible amount of wildlife, especially all types of birds. The home has sunny views everywhere. Seasonal weeds do grow in the adjacent lake which can impact water activities, especially in the summer months. Sleeps 6. Ther are two full and one 1/2 baths.

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 Lanesborough outdoor seating rentals
House rentals with outdoor seating

Elmwood Farmhouse

Cleveland House - renovated Berkshires' gem.

A paradise in the woods, minutes from MASS MoCA

Cozy Modern Sugar House with spectacular views.

Chic Hudson Farmhouse w/ Fireplace & Porch

19th c. Barn in The Berkshires

Cheerful Catskill Village Cottage

Brooksong, the perfect Berkshires getaway
Apartment rentals with outdoor seating

Historic Victorian - Entire 3rd floor

Beautiful space in the heart of Philmont

Overlooking the city in a quiet 7 unit building.

Sunny carriage house apartment

Cooper's Place

Mountain View Retreat~Sunny Hill Golf / Skiing

COLD SPRING

Hudson River Beach House
Condo rentals with outdoor seating

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

Mount Snow Ski Chalet

Spacious 3 bedroom apt in Lenox historic downtown

Winter Dream! The Handle Lodge at Snowtree Condos

Ideal location! Steps to Track and Broadway!

Condo w/ great amenities 4-seasons! Ski in Ski out

Ski Condo 5 Min from Mt Snow

Wyndham Bentley Brook
When is the best time to visit Lanesborough?
Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
---|---|---|---|---|---|---|---|---|---|---|---|---|
Avg. price | R5,490 ZAR | R6,082 ZAR | R5,263 ZAR | R5,228 ZAR | R5,664 ZAR | R5,664 ZAR | R5,228 ZAR | R5,559 ZAR | R5,228 ZAR | R5,333 ZAR | R5,228 ZAR | R5,890 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 Lanesborough
Total vacation rentals
Explore 80 vacation rentals in Lanesborough
Nightly prices starting at
Lanesborough vacation rentals start at R1,568 ZAR per night before taxes and fees
Verified guest reviews
Over 3,250 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
30 properties feature pools
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wi-Fi availability
80 of Lanesborough vacation rentals include wi-fi access
Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Lanesborough rentals
4.9 Average rating
Lanesborough stays are highly rated by guests—averaging 4.9 out of 5!
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- Stratton Mountain
- Six Flags New England
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Zoom Flume
- Catamount Mountain Ski Resort
- Saratoga Spa State Park
- Norman Rockwell Museum
- Taconic State Park
- 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
- Beartown State Forest
- Albany Center Gallery
- Peebles Island State Park
- Berkshire Botanical Garden