
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.

Hoppy Hill Farm House
Enjoy the simple country life in this historic farmhouse. Watch the sun rise over the breathtaking mountain views from the front porch while sipping a cup of coffee/tea. For the more adventurous, there are lots of Appalachian Trail hiking opportunities, and nature preserves to enjoy. Plenty of quaint towns near-by: Kent, Millbrook, Amenia, Wassaic for great food, coffee shops, antiques, parks, breweries and vineries. Inside, you will feel right at home in this comfortable one bedroom apartment.

Quiet Studio Apartment in Pawling
For getaways or visiting the area, this peaceful sanctuary awaits your arrival in Pawling. A fresh clean studio apartment with idyllic views of the forest, stone walls, and distant mountains. Awake to the sound of birds and beautiful sites. With a king size bed, kitchenette, desk, Smart TV, WIFI, full bath with walk-in shower. Big sliding glass door to private deck overlooking native landscaping. 1 mile to village for restaurants, bakeries, & night spots. 7 min by taxi to Darryl's House Club.

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.
It’s time to book your FALL LEAF-PEEPING sojourn at the Huckleberry Quarters, a beautifully renovated 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 this FALL, a writer or artist's retreat. Easy access to Merritt Parkway, trains, local eateries, parks.

Boulder Tree House
Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

French Guest House in Waccabuc
A mini Versailles just outside of NYC - located on a private and gated eight acre estate with its own lake in Waccabuc, NY. Surrounded by 18C statuary, manicured gardens and fountains, it’s equivalent to staying in a 5-Star European luxury hotel suite (house designed by David Easton) with its heated stone floors and heated towel rack, luxury linens, gold taps and serene private entrance. (.7mi from Waccabuc Country Club, 60 min from NYC by car or train - Katonah train St)

The Cove Cabin
An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

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.

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.

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

Pet friendly Scenic Home

❤️ Your Silvermine Hideaway, nestled in nature.

Spectacular Lake Views from Every Room & Garden

Top Rated Gem | Fire Pit | BBQ | FFU | Near Beach

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

Lakeview Estate - Chef's Kitchen - NYC Getaway

Historic Hideaway - Spacious home - Lake Access

Casa Luna Lake House
Apartment rentals with outdoor seating

Foxglove Farm

Luxury 2bd⭐Comfort+Style⭐

Union 2BR Resort-Style Apt – Easy NYC Transit

Wooded stream side Retreat

Comfy 2BR Apt with private entry & free parking.

"Triplex Historic Beauty" with Seasonal Garden

The Hideaway

Retreat in New Haven by Stephanie and Damian
Condo rentals with outdoor seating

New 3BR Condo w/Rooftop Terrace & NYC Views

Cozy Condo by Fairfield U/SHU | Patio | Wshr/Dryr

Stylish Liberty Condo | 20-Min to NYC | Skyline

Hoboken apt with new bathroom & private terrace!

Cozy West Point Hide Away and Cadet’s Get Away

Private European Garden Apartment

Entire Place_Upscale Sunny Duplex w/Large Backyard

Cozy Stylish retreat - NYC & NWK w/free parking
When is the best time to visit Lewisboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $624 NZD | $624 NZD | $624 NZD | $568 NZD | $586 NZD | $734 NZD | $837 NZD | $823 NZD | $675 NZD | $634 NZD | $659 NZD | $624 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 $249 NZD per night before taxes and fees

Verified guest reviews
Over 2,350 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
60 properties have a dedicated workspace

Wi-Fi availability
70 of Lewisboro holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- The Hamptons Holiday rentals
- Rentals with a fireplace Lewisboro
- Rentals with a patio Lewisboro
- Fitness-friendly rentals Lewisboro
- Pet-friendly rentals Lewisboro
- Rentals with lake access Lewisboro
- Rentals with a washing machine and dryer Lewisboro
- Rentals with a fire pit Lewisboro
- Family-friendly rentals Lewisboro
- House rentals Lewisboro
- Rentals with pools Lewisboro
- Rentals with outdoor seating Westchester County
- Rentals with outdoor seating New York
- Rentals with outdoor seating United States
- Times Square
- Rockefeller Center
- Bryant Park
- Madison Square Garden
- Columbia University
- Yale University
- Central Park Zoo
- MetLife Stadium
- Jones Beach
- Mountain Creek Resort
- Yankee Stadium
- Fairfield Beach
- Citi Field
- United Nations Headquarters
- Empire State Building
- Grand Central Terminal
- Statue of Liberty
- Radio City Music Hall
- Rye Beach
- Canarsie Beach
- USTA Billie Jean King National Tennis Center
- The Metropolitan Museum of Art
- Gilgo Beach
- Astoria Park




