
Holiday rentals with outdoor seating in Lewisboro
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Lewisboro
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

Serene Pond Views Charming private patio…
Country Charm Awaits. 45 miles north of George Washington Bridge. Our 2 room efficacy apartment w. microwave, mini fridge & private entrance + parking space. Great WiFi, Apple TV. Enjoy views overlooking Henderson Pond. 1/4 walk to Query State Park, 36 acres w. trails. Our apartment is 4 miles from town of Ridgefield, 3 miles from Wilton town center, 6 miles from New Caanan & 8 miles from Westport Town Center. We have a couple of small puppies who will welcome you too. So we don’t allow pets…

Special Nest w Private Entrance River View Porches
Front and back porch, river views, spacious living areas, new & fresh kitchen, and *two* bathrooms make this apartment the ultimate landing spot for a fun vaycay! Located on a street filled with intricate historical homes, this first floor apartment offers an accessible and comfortable getaway. A large backyard is shared with other guests, and sweeping river views are only steps away from your front door. Private entrance, plus easy parking and an electric car charger if you need it!

Huckleberry Quarters, the Cozy Redding Retreat.
It’s time to book your Winter holiday at the Huckleberry Quarters, a beautifully appointed studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A peaceful country getaway to enjoy any season, a writer or artist's retreat. Easy access to Merritt Parkway, trains, local eateries, parks.

Comfortable home away from home- near everything
Price includes Airbnb fees. Cozy, pet-friendly cottage in a peaceful setting just 70 miles from NYC and minutes from I-84 (Exit 8 or 9). This clean & comfortable retreat features 3 bedrooms (2 queens, 1 full), and pull-out couch. Portable A/C's in summer, and fireplace for cozy nights. The greenhouse adds plenty of natural light, the yard is perfect for kids, the front deck is great for morning coffee, and the gas grill great for cooking out. High-speed WiFi and 3 smart TVs.

Sweet, stylish cabin in the woods- hiking & more!
Only an hour north of NYC, but a world away! Adorable cabin in the woods offering stylish updated decor and beautiful natural surroundings. Brand new and completely renovated interior, but all the classic charm of the country. Trade in skyscrapers for tall trees in this sweet country escape that is near Fahnestock Park (surrounded by great hiking, skiing, etc) and 15m from the village of Cold Spring. Fully set up w/ wifi, Netflix & more! Quiet, considerate guests only please!

Peaceful apartment on 3.5 acres w/ Artist studio.
Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Guest suite with private enter
Private room with private enter and bathroom attached dedicated work space and privat parking. On a 1.5 acres property. With fast internet. Located 5 minutes of walking distance from ASML office park, 5 minutes drive from Norwalk corporate park, 9 minutes drive from Wilton Downtown and 15 min drive from Norwalk train station. Close to a lot of restaurants, coffee shops, stores and parks. The owners live in other part of the house. Family owns cats.

French Guest House in Waccabuc
A private, European-style retreat just 60 minutes from NYC. Set on an eight-acre gated French estate with its own lake, this guest house feels like a mini Versailles with 18th-century statuary, fountains and manicured gardens. Designed by David Easton, it features heated stone floors, a heated towel rack, luxury linens, gold fixtures, fast WiFi, and a private entrance. Minutes from Waccabuc Country Club and the Katonah train station.

Peaceful Light-Filled Guesthouse 1 Hour From NYC
Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Escape to a Restored New England Antique Milk Barn
A Bucolic antique farm property in the Fairfield County countryside. Welcome to Connecticut country living at its best! Enjoy the gardens from your private patio, take a dip in the pool, read a book surrounded by fall foliage and retire to your very private suite and relax in the soaking tub. Please note the owners reside on the 4 acre property but give guests the utmost privacy.

Bedford Paradise Getaway | Hot Tub | Town Center
Escape to the enchanting town of Bedford, NY, where a world of tranquility and luxury awaits you. Nestled amidst rolling hills and picturesque landscapes, our exquisite Airbnb offers the perfect blend of rustic charm and modern comforts. This impressive 3-bedroom, 2.5-bathroom haven promises an unforgettable stay, where sophistication and relaxation blend seamlessly.

NY Rustic Cottage Getaway
Just 50 min North of NYC (Metro North 5 min away) great for artists, writers, yogi's and creative types or people just wanting to get away from the hustle and bustle, city amenities near by. (Photo Shoots, Seminars, Workshops welcome-Call For different Rates) Tag & Follow Nina’s Cottage on Insta! @ninas_airbnb
Popular amenities for outdoor seating rentals in Lewisboro
House rentals with outdoor seating

Lower Hudson Valley Idyllic Retreat

Tranquil Tree-House on the beautiful Hudson River

1840Farmhouse, 65"OLED4k, firepit, 3x4ktvs, 3acres

Historic Hideaway - Spacious home - Lake Access

Casa Luna Lake House

Private farm cottage +hiking

Bright Stylish Chic 4BR 4BA Home

Gem by the water+ firepit and all fenced backyard
Apartment rentals with outdoor seating

Foxglove Farm

Luxury 2bd⭐Comfort+Style⭐

The Hillside Crib | 1 Bedroom Apt | Near Downtown

HighLineHarbor Flat2BD|Train2NYC|HarborPointAccess

Comfy 2BR Apt with private entry & free parking.

"Triplex Historic Beauty" with Seasonal Garden

Suite74 - Cozy, modern 1 bedroom with office

Cozy 2 Bedroom Apt King & Queen 15 minutes to nyc
Apartment rentals with outdoor seating

Cozy 1BR Apartment | Near Manhattan

1856 Trading House w/ walk to water

Cozy 3-Bed 2-Bath Condo | Parking and Laundry!

Brand new apt - conveniently located close to NY

Studio Apartment- 15 Min. to NYC

Private European Garden Apartment

chic brownstone retreat

Chic Retreat Near Manhattan!
When is the best time to visit Lewisboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $451 SGD | $451 SGD | $451 SGD | $411 SGD | $424 SGD | $531 SGD | $606 SGD | $595 SGD | $488 SGD | $459 SGD | $477 SGD | $451 SGD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Quick stats about holiday rentals with outdoor seating in Lewisboro

Total holiday rentals
Explore 70 holiday rentals in Lewisboro

Nightly prices starting at
Lewisboro holiday rentals start at $103 SGD per night before taxes and fees

Verified guest reviews
Over 2,410 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
70 of Lewisboro holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Lewisboro rentals

4.9 Average rating
Lewisboro stays are highly rated by guests – averaging 4.9 out of 5!
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- Family-friendly rentals Lewisboro
- Rentals with a firepit Lewisboro
- Rentals with a patio Lewisboro
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- Rentals with outdoor seating Westchester County
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- Rentals with outdoor seating United States
- Times Square
- Rockefeller Center
- Madison Square Garden
- Grand Central Terminal
- Bryant Park
- New York Public Library Main Branch
- Brooklyn Bridge
- Central Park Zoo
- MetLife Stadium
- Yale University
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- Mountain Creek Resort
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- 47th–50th Streets Rockefeller Center Station
- Rough Trade
- Top of the Rock
- Yankee Stadium
- Chabad Lubavitch World Headquarters
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- Citi Field
- Empire State Building




