
House vacation 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!

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!

Luxury Lake House Sauna 1h From NYC
Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC

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

Private Hudson Valley Country Retreat

Entire Home (private pool), Event Friendly

Gameroom, backyard + pool! 7m to train + downtown

Midcentury Modern ZenHouse Sculptor Studio

North Salem Home with Pool & Great Yard

Port Jefferson Convenient, Cozy and Chic!

Stunning Views, Bucolic Bliss in 1790s Farmhouse

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

Pet friendly Scenic Home

❤️ Your Silvermine Hideaway, nestled in nature.

Historic wooded 3BD 1 hour from NYC

Nature Lover's Retreat in Mount Kisco

4 Seasons By The Lake 3 bedroom Luxurious Home

Quiet and Cozy Cottage near NYC with a Pond

A nice place to getaway

Nature Retreat Airbnb
Private house rentals

5 Minute Walk to Beach & Downtown Fairfield

Historic Designer City Getaway

Serene Retreat in the Hills w/Jacuzzi

Modern Tranquil Home In Connecticut- 40 min to NYC

Riverfront Cottage-Pool-Hot Tub-Fireplace 35m>NYC

Arkadia House Mid-century retreat with pool & view

Cozy studio quiet and safe

Magical Weston Retreat
When is the best time to visit Lewisboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $629 CAD | $591 CAD | $629 CAD | $666 CAD | $629 CAD | $657 CAD | $685 CAD | $721 CAD | $629 CAD | $629 CAD | $699 CAD | $665 CAD |
| 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 vacation rentals
Explore 80 vacation rentals in Lewisboro

Nightly prices starting at
Lewisboro vacation rentals start at $84 CAD per night before taxes and fees

Verified guest reviews
Over 1,550 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
80 of Lewisboro vacation 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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- Rentals with a patio Lewisboro
- Rentals with a fireplace Lewisboro
- Rentals with a washer and dryer Lewisboro
- Pet-friendly rentals Lewisboro
- Rentals with a firepit Lewisboro
- Rentals with pools Lewisboro
- Fitness-friendly rentals Lewisboro
- Rentals with lake access Lewisboro
- Family-friendly rentals Lewisboro
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- Times Square
- Rockefeller Center
- Madison Square Garden
- Bryant Park
- New York Public Library - Bloomingdale Library
- Grand Central Terminal
- Columbia University
- Central Park Zoo
- Yale University
- MetLife Stadium
- Jones Beach
- Mountain Creek Resort
- Yankee Stadium
- United Nations Headquarters
- Citi Field
- Fairfield Beach
- Empire State Building
- Statue of Liberty
- Radio City Music Hall
- Canarsie Beach
- USTA Billie Jean King National Tennis Center
- Rye Beach
- The Metropolitan Museum of Art
- Astoria Park




