
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.

1956 House of the Year Award. Easy commute to NYC.
Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

Bright&Comfy 2bed/1ba in quiet duplex
Bright, comfortable & quiet! Just outside downtown White Plains, this home has a relaxing living space with thoughtful touches. It offers easy accessibility to New York City (35 min Via Metro North) and Westchester (via highways and local buses). The house is set up for WFH, with great wifi via Verizon. It's an easy jump off spot for a fun weekend in Westchester. It comes with a dedicated parking spot, never worry about your vehicle! Bars, restaurants, shopping, groceries are all minutes away!

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.

Peaceful Suburban Colonial w/New Kitchen.
Looking for a clean, cozy, secluded suburban escape that's still close to great shopping, Long Island Sound, and the two Fairfield Universities? Look no further than this newly renovated colonial on a quiet tree-lined street with no through traffic. A park and basketball are just at the end of the street. Trader Joes and other great shopping are a 2 minute drive away. Sacred Heart and Fairfield U are 5 minutes away. We're right across the street in case any of us forgot anything :).

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.

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

Joyful Beach House, viewing The Great South Bay

Private Hudson Valley Country Retreat

midcentury mod * HOT TUB * walk out trail 2 mohonk

Entire Home (private pool), Event Friendly

4Br Mountain Brook House on 130 acres w/ trails

Country Retreat | Fire Pit | BBQ

Port Jefferson Convenient, Cozy and Chic!

Stunning Views, Bucolic Bliss in 1790s Farmhouse
Weekly house rentals

Serene Retreat in the Hills w/Jacuzzi

North Salem Home with Pool & Great Yard

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

Historic wooded 3BD 1 hour from NYC

Nature Lover's Retreat in Mount Kisco

Quiet and Cozy Cottage near NYC with a Pond

A nice place to getaway

Comfortable Mid-Century on Quiet Country Road
Private house rentals

Farmhouse & private yard

Westport: Deco HAUS 5 min to Town /10 min to Beach

Comfy welcoming home in bucolic setting

Modern Tranquil Home In Connecticut- 40 min to NYC

Hilltop Retreat- Lakefront with Dock

Arkadia House Mid-century retreat with pool & view

Meeker Hill House - Country Escape w/ Heated Pool

4Bds Rustic Retreat with hot tub & mini golf
When is the best time to visit Lewisboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $694 AUD | $652 AUD | $694 AUD | $736 AUD | $694 AUD | $725 AUD | $756 AUD | $796 AUD | $694 AUD | $694 AUD | $771 AUD | $734 AUD |
| 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 $93 AUD per night before taxes and fees

Verified guest reviews
Over 1,550 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 outdoor seating Lewisboro
- Fitness-friendly rentals Lewisboro
- Pet-friendly rentals Lewisboro
- Rentals with a washing machine and dryer Lewisboro
- Rentals with lake access Lewisboro
- Rentals with a fireplace Lewisboro
- Rentals with a patio Lewisboro
- Rentals with pools Lewisboro
- Rentals with a fire pit Lewisboro
- Family-friendly rentals Lewisboro
- House rentals Westchester County
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- Times Square
- Rockefeller Center
- Bryant Park
- Madison Square Garden
- Empire State Building
- Columbia University
- Yale University
- MetLife Stadium
- Central Park Zoo
- Jones Beach
- Yankee Stadium
- Mountain Creek Resort
- Fairfield Beach
- Citi Field
- United Nations Headquarters
- Grand Central Terminal
- Rye Beach
- Statue of Liberty
- USTA Billie Jean King National Tennis Center
- Radio City Music Hall
- Canarsie Beach
- Gilgo Beach
- The Metropolitan Museum of Art
- Robert Moses State Park