
Holiday rentals with outdoor seating in Lewisboro
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Lewisboro
Guests agree: These Holiday Houses 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…

Huckleberry Quarters, the Cozy Redding Retreat.
Now is the time to book your SPRING 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.

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!

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.

"Triplex Historic Beauty" with Seasonal Garden
Featured on the History Channel hit TV series "American Pickers"! Come join us at the head of the harbor in historic downtown Norwalk "Wall Street" neighborhood. This cozy second floor rental has been tastefully decorated with new and old. In addition to the photo descriptions we have included a floor plan for review. Please note the neighborhood is a working waterfront during the day and the Danbury active train line runs behind the building which adds to the character .

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.

The Cottage by the Lake: Hudson Valley Indulgence
The Cottage by the Lake is a cozy, secret get-away on the scenic banks of the Croton Watershed. About an hour from NYC, it’s on the property of an 1850 farmhouse & has a fully equipped kitchen & bath, cathedral ceiling, working fireplace & cozy sleeping loft. The patio has a fire pit and gas bbq. It’s the ideal place for those seeking to work from home.

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 Lewisboro outdoor seating rentals
Holiday House Rentals with Outdoor Seating

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

Historic Hideaway - Spacious home - Lake Access

Casa Luna Lake House

Family Cottage with 4 King Beds and Fire Pit

Your Perfectly Wonderful Woodbury Sanctuary!

A nice place to getaway

Luxurious Barn With New England Charm

Waterfront Lake House
Apartment rentals with outdoor seating

Foxglove Farm

Luxury 2bd⭐Comfort+Style⭐

Honey Spot Studio | Downtown City Views

Riverview Rowhouse, a vintage modern home

The Hideaway

Luxurious 1BR Downtown Stamford

Dream getaway apartment in the foot of Gunks Ridge

Cozy Apartment with Water View of Brook
Condo rentals with outdoor seating

Spacious 1BR Condo ~ 25min to NYC! + Free Parking

New 3BR Condo w/Rooftop Terrace & NYC Views

Stylish Retreat with Garden, Deck & Private Entry

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

Hoboken apt with new bathroom & private terrace!

Easy commute Cozy Studio in Jersey City

Private European Garden Apartment

1BD in Hoboken + Deck
When is the best time to visit Lewisboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $594 NZD | $594 NZD | $594 NZD | $542 NZD | $559 NZD | $700 NZD | $798 NZD | $785 NZD | $644 NZD | $618 NZD | $627 NZD | $723 NZD |
| 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 $136 NZD 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 and kid-friendly amenities

Pet-friendly accommodation
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

Wi-Fi availability
70 of Lewisboro holiday rentals include Wi-Fi 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!
Destinations to explore
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- Family-friendly rentals Lewisboro
- Rentals with lake access Lewisboro
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- Rentals with a fireplace Lewisboro
- Rentals with a patio Lewisboro
- Rentals with outdoor seating Westchester County
- Rentals with outdoor seating New York
- Rentals with outdoor seating United States
- Times Square
- Rockefeller Center
- Madison Square Garden
- Bryant Park
- Brooklyn Bridge
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Yale University
- Grand Central Terminal
- Bronx Zoo
- Mountain Creek Resort
- Old Glory Park
- Ohel Chabad-Lubavitch
- Yankee Stadium
- Jones Beach
- United Nations Headquarters
- Chabad Lubavitch World Headquarters
- Empire State Building
- Citi Field
- Statue of Liberty
- Radio City Music Hall
- Fairfield Beach
- New York Public Library Main Branch




