
House holiday rentals in Lewisboro
Find and book unique houses on Airbnb
Top-rated house rentals in Lewisboro
Guests agree: These houses are highly rated for location, cleanliness and more.

Lux Bungalow on the Lake
Beautiful, light flooded, waterfront home 1 hour from New York City. The 2 bedroom home is on picturesque Lake Carmel. Wake up, eat, sleep and relax to the tranquil view of the glistening water - truly an oasis! Take in a sunset while eating a meal at home, explore the shops and restaurants in a cute nearby town, take a walk around the lake, read a book by the cozy fireplace, hike, cook, kayak, ski, or just sit and enjoy. Centrally located close to Hudson Valley, Westchester and Connecticut.

Lower Hudson Valley Idyllic Retreat
Located 2 minutes from Teatown Nature Reserve (35 mins from NYC) on 1+ acre in the Lower Hudson Valley, this updated 2,600sf oasis is the perfect forest setting for your family or business retreat. It features an oversized gourmet chef's kitchen with adjoining dining room. There are 4 bedrooms, including a nursery/crib, additional sleeping spots, and stunning views from a perfectly perched solarium. The great room features a spectacular working fire place and floor to cathedral ceiling windows.

Spacious 3b/3b Mediterranean in White Plains
Bring the whole family to this great place with lots of room for fun, relaxation or hosting! This 3bed/3bath Mediterranean is freshly renovated with stylish touches & comfy furniture. The main floor of this multi family serves as a great spot to bring the family while visiting the area. The house boasts an oversized living room, formal dining room, large chef's kitchen, and plenty of sleeping space. With heat & AC throughout the entire 2k sf unit, this house is great for anything& everything!

Midcentury Modern ZenHouse Sculptor Studio
Mid-century modern historic private estate surrounded by river @Zenhouse_satori and main house. Great for memorable romantic getaway, photoshoots and film locations! ZENHOUSE mission is rooted in the values of respect, creativity, and excellence. Inspired by the timeless principles of Zen, we offer a luxurious and exclusive experience where tranquility blends with art, spirituality, and nature. We provide a serene environment and personalized service to awaken your true nature and find Zen

Family Cottage with 4 King Beds and Fire Pit
Escape to Norwalk Cottage, a beautifully designed 4-bedroom, 2-bath home perfect for 8 guests. This family-friendly getaway features a fully stocked kitchen, cozy fireplace, and a fun basement playroom. Relax in the private backyard with a deck, grill, and fire pit. Located on the quiet Norwalk/Westport border, you're just minutes from Calf Pasture Beach, great restaurants, and the vibrant SoNo district. Enjoy central air, fast WiFi, and a dedicated workspace for the perfect year-round escape.

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.

The Cozy Little Cottage
Charming guest apartment on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is a good size for 1-2 adults, can fit 3 people if one is a child. The unit is separate from our house, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed. We have a twin air mattress for use in the living room.

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.

Cozy getaway 1 hr from NYC!
This peaceful home is only 1 hour from NYC & Brooklyn. There are 3 bedrooms & 3 bathrooms. A large living area, a play room, a wood burning FIREPLACE, large TRAMPOLINE, yard with babbling brook! Bedroom 1: King size bed, pack n play, toddler bed. Ensuite bathroom. Bedroom 2: Queen size bed, dresser. Ensuite bathroom. Bedroom 3: King size bed, pull out couch. Ensuite bathroom. Living room: Pull out couch. Pool is open Memorial Day - Labor Day. Heated by the sun- no heater.

Lakeview Estate - Chef's Kitchen - NYC Getaway
Stunning lake views from every angle! Gorgeous 3,200 square foot custom home with an open floor plan. Highlights include: * Chef's kitchen with Viking Range, Sub Zero Refrigerator, granite countertops & custom cabinets * Expansive 20x30 stone patio overlooking the lake with a fire-pit, speakers & outdoor lighting * 3 spacious bedrooms and 3 full bathrooms with double vanities, showers & separate bathtubs. * 5 SmartTVs including a 65" TV in the main living area

Gem by the water+ firepit and all fenced backyard
Take it easy at this unique and tranquil getaway. One block away from the water and three blocks away from Dolphin Cove. Enjoy walkings and site-seeings. Perfect for going kayaking, paddle boarding or just stay relaxing in the backyard. It is located at 5 minutes walking distance from the train station and 7 minutes away from downtown. Bus stop in front of the house. The house has a lower level that mostly is occupied by the host and sometimes with guests.

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.
Popular amenities for Lewisboro house rentals
House rentals with a pool

Private Hudson Valley Country Retreat

midcentury mod * HOT TUB * walk out trail 2 mohonk

Entire Home (private pool), Event Friendly

Hilltop House w/POOL/SPA- HOST & Co.

BoHo Scandi Farm Retreat, Fireplace, Dogs Welcome

Port Jefferson Convenient, Cozy and Chic!

Log House, sits on 3acres. A retired mini farm.

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town
Weekly house rentals

North Salem Home with Pool & Great Yard

Hudson Valley Bungalow Retreat ~1 hr from NYC

4 Seasons By The Lake 3 bedroom Luxurious Home

Cozy Studio in Bridgeport

Comfortable Mid-Century on Quiet Country Road

Cozy Private Suite Near Train to NYC

1 King Bed/1 Bath 750 SF Cottage Loft Style Home

Chic Midcentury Retreat with Private Pond near NYC
Private house rentals

❤️ Your Silvermine Hideaway, nestled in nature.

Country Escape from the City! -walk from train

A nestled retreat on 15 acres

Pet Frndly Lake House w/Fireplace & Fire Pit W/D

Nature Lover's Retreat in Mount Kisco

Quiet and Cozy Cottage near NYC with a Pond

Private Suite in the Heart of the Hudson Valley

Entire House on Scenic Estate with Private Pond
When is the best time to visit Lewisboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $784 NZD | $737 NZD | $784 NZD | $831 NZD | $784 NZD | $818 NZD | $853 NZD | $898 NZD | $784 NZD | $784 NZD | $871 NZD | $829 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 house rentals in Lewisboro

Total holiday rentals
Explore 80 holiday rentals in Lewisboro

Nightly prices starting at
Lewisboro holiday rentals start at $104 NZD per night before taxes and fees

Verified guest reviews
Over 1,650 verified reviews to help you choose

Family-friendly holiday rentals
60 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 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
80 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
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- Rentals with a fire pit Lewisboro
- Fitness-friendly rentals Lewisboro
- Rentals with a fireplace Lewisboro
- Rentals with outdoor seating Lewisboro
- Pet-friendly rentals Lewisboro
- Rentals with pools Lewisboro
- Rentals with a washing machine and dryer Lewisboro
- Rentals with a patio Lewisboro
- Family-friendly rentals Lewisboro
- Rentals with lake access Lewisboro
- House rentals Westchester County
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- Times Square
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- Grand Central Terminal
- Bryant Park
- New York Public Library Main Branch
- Brooklyn Bridge
- Central Park Zoo
- MetLife Stadium
- Yale University
- Ohel Chabad-Lubavitch
- Mountain Creek Resort
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- The High Line
- Manhattan Bridge
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- Rough Trade
- 47th–50th Streets Rockefeller Center Station
- Top of the Rock
- Yankee Stadium
- Chabad Lubavitch World Headquarters
- United Nations Headquarters
- Citi Field
- Empire State Building




