Best Vacation Homes in Lewisboro
Cottage
9.6(7 Reviews)
1 Bedroom
1 Bath
6 Guests
950 ft²
Fireplace/Heating
Ocean View
Balcony/Terrace
View
US $311/Night
7 Nights - US $2,175
House
10.0(1 Review)
4 Bedrooms
4 Baths
8 Guests
5102.09 ft²
Oceanfront
Hot Tub
Spa- Fireplace/Heating
US $1,023/Night
7 Nights - US $7,164
Bed & Breakfast
9.8(54 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Breakfast
Kitchen
US $430/Night
7 Nights - US $3,009
Cottage
9.4(42 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Fireplace/Heating
Pet Friendly- Kitchen
Parking
US $281/Night
7 Nights - US $1,967
House
6.0(1 Review)
1 Bedroom
1 Bath
6 Guests
947.22 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
US $319/Night
7 Nights - US $2,233
Apartment
3.0(4 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $195/Night
7 Nights - US $1,368
Hotel
10.0(2 Reviews)
1 Bath
- Fireplace/Heating
- Breakfast
- Parking
Air Conditioner
US $472/Night
7 Nights - US $3,302
Hotel
10.0(1 Review)
1 Bath
- Fireplace/Heating
- Breakfast
- Parking
- Air Conditioner
US $486/Night
7 Nights - US $3,404
Lewisboro Luxury Rentals
House
10.0(1 Review)
8 Bedrooms
4 Baths
12 Guests
5000 ft²
Private Pool- Hot Tub
- Fireplace/Heating
Pool
US $3,375/Night
7 Nights - US $23,623
House
10.0(6 Reviews)
5 Bedrooms
4 Baths
10 Guests
5400 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $1,457/Night
7 Nights - US $10,198
House
9.6(49 Reviews)
6 Bedrooms
6 Baths
15 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Ocean View
US $1,267/Night
7 Nights - US $8,872
House
10.0(9 Reviews)
3 Bedrooms
2 Baths
7 Guests
- Private Pool
- Spa
- Fireplace/Heating
- Pool
US $982/Night
7 Nights - US $6,874
US $884/Night
7 Nights - US $6,186
House
9.6(5 Reviews)
4 Bedrooms
2 Baths
8 Guests
3450 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $815/Night
7 Nights - US $5,708
Hotel
2 Baths
- Balcony/Terrace
- Breakfast
- Kitchen
- Parking
US $727/Night
7 Nights - US $5,089
House
9.0(9 Reviews)
3 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $563/Night
7 Nights - US $3,944
Lewisboro Pet Friendly Vacation Rentals
House
9.8(6 Reviews)
3 Bedrooms
2 Baths
5 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $362/Night
7 Nights - US $2,534
New
House
1 Bedroom
2 Baths
6 Guests
18836.84 ft²
Private Beach- Oceanfront
- Fireplace/Heating
- Ocean View
US $451/Night
7 Nights - US $3,159
Apartment
9.8(6 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $305/Night
7 Nights - US $2,135
Hotel
8.6(39 Reviews)
9 Baths
314.55 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
US $322/Night
7 Nights - US $2,254
Cottage
4 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Parking
US $787/Night
7 Nights - US $5,506
House
3 Bedrooms
3 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Pet Friendly
US $893/Night
7 Nights - US $6,254
House
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
Internet
US $345/Night
7 Nights - US $2,415
House
8.8(8 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $262/Night
7 Nights - US $1,834
Lewisboro Large Vacation Homes
House
5.0(1 Review)
5 Bedrooms
4 Baths
8 Guests
- Private Pool
- Pool
- Kitchen
- Air Conditioner
US $949/Night
7 Nights - US $6,643
House
2.0(1 Review)
6 Bedrooms
5 Baths
12 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
US $659/Night
7 Nights - US $4,610
House
5 Bedrooms
3 Baths
12 Guests
- Air Conditioner
- Child Friendly
Laundry
Bedding/Linens
US $750/Night
7 Nights - US $5,250
Why Choose Rent By Owner for your Lewisboro Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Lewisboro
When should you plan your Vacation Rentals stay?
Choosing the optimal time to vacation here ensures you experience the region's natural beauty and tranquility at its best, making your stay in Lewisboro, New York, truly memorable.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this period, the area experiences warm daytime temperatures ideal for outdoor activities and exploring the scenic countryside.
Average Temperature Daytime: 70°F - 80°F - Nighttime: 50°F - 60°F
Autumn (September to October)
This season offers vibrant fall foliage, making it a popular time for taking in the natural beauty of the region while enjoying comfortable weather.
Average Temperature Daytime: 65°F - 75°F - Nighttime: 45°F - 55°F
Off-Season Highlights
Winter (December to February)
The colder months bring fewer visitors, providing a peaceful retreat with crisp air and a serene winter landscape for those seeking quiet relaxation.
Average Temperature Daytime: 30°F - 40°F - Nighttime: 20°F - 30°F
Late Fall to Early Winter (November)
As the region transitions into winter, fewer travelers visit, creating a perfect opportunity for those who prefer a tranquil getaway before the holiday rush.
Average Temperature Daytime: 45°F - 55°F - Nighttime: 35°F - 45°F
Weekly Weather Forecast for Lewisboro
How to Book Your Lewisboro Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Lewisboro
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor seating area perfect for relaxing and dining amidst the natural beauty of the region.
- Take advantage of spacious gardens or lawns ideal for outdoor activities and family gatherings.
- Make the most of a swimming pool to cool off during warm days in this scenic destination.
- Benefit from a covered patio or veranda that offers a comfortable spot to enjoy the fresh air regardless of the weather.
- Discover opportunities for outdoor grilling with a dedicated barbecue area, perfect for socializing with friends or family.
- Explore nearby walking trails or nature paths conveniently accessible from your rental house or cabin.
- Relax by a fire pit in the evenings, creating memorable moments under the stars in this peaceful part of the region.
Top Attractions Around Lewisboro
What attractions are nearby?
In this inviting destination, you can explore outdoor activities such as hiking and birdwatching at nearby parks, or enjoy tranquil moments by scenic lakes just a short drive away, offering a perfect blend of natural beauty and outdoor recreation for your stay.
Family Activities
- Lewisboro Nature Walks: Explore scenic trails around the area, perfect for family hikes and outdoor adventures that connect you with nature.
- Bear Mountain State Park: Visit this nearby park offering family-friendly activities like picnicking, biking, and enjoying the picturesque views of the Hudson River.
- Local Farm Visits: Experience the charm of regional farms where children can learn about agriculture and participate in seasonal farm activities.
- Community Events and Festivals: Engage with the area's vibrant community through seasonal festivals, outdoor concerts, and family-oriented celebrations hosted locally.
Adult Activities
- Hiking at Ward Pound Ridge Reservation: Explore scenic trails and enjoy the natural beauty that makes this destination a perfect spot for outdoor enthusiasts seeking adventure in nature.
- Golf at the Whitestone Golf Club: Tee off on well-maintained courses designed for players of all skill levels, providing a relaxing yet active day here in the region.
- Visit the John Jay Homestead State Historic Site: Discover the rich history of the area through guided tours and exhibits at this historic site dedicated to one of America’s founding fathers.
- Attend local art and cultural events: Engage with the vibrant arts scene by attending festivals and exhibitions that showcase regional talent and creativity throughout the area.
Lewisboro Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Nature: Take advantage of the scenic outdoor spaces nearby to enjoy activities like hiking or picnicking, making your stay in this area truly refreshing.
- Visit Seasonal Events: Check out local events and festivals during your visit to immerse yourself in the region's vibrant community atmosphere.
- Plan Your Transportation: Arrange reliable transportation options early to easily access the attractions and amenities within the region without hassle.
- Choose the Right Vacation Rental: Select a well-located rental property that offers comfort and convenience, ensuring a memorable experience here.
Transportation Options
- Metro-North Railroad: This commuter train service offers convenient access to New York City and surrounding areas, ideal for exploring the region from your vacation rental.
- Local Bus Services: Regional bus lines provide affordable transportation within the area, making it easy to navigate here without a car.
- Rental Car Services: Numerous car rental agencies operate nearby, giving you the flexibility to explore more remote spots at your own pace during your stay.
- Taxi and Ride-Sharing Services: Taxis and ride-sharing options like Uber and Lyft are readily available, providing quick transportation around this destination's local attractions.
Local Customs Options
- Local Harvest Festivals: In the region, annual harvest festivals celebrate community and agricultural traditions, offering a glimpse into the area's rural heritage.
- Historical Preservation Customs: Respect for historical sites and preservation efforts are prominent here, reflecting the community’s dedication to maintaining its local history.
- Community Volunteer Events: Participating in neighborhood cleanup days and charity events is a common way residents show their commitment to the area's well-being.
- Regional Culinary Traditions: Dining customs often highlight locally sourced ingredients, showcasing the area’s farm-to-table culinary scene that visitors can enjoy during their stay.
Lewisboro Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Lewisboro?
There are a lot of options in Lewisboro. If you plan on staying in the Lewisboro area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Lewisboro:
- Charming Cottage located on Historic Estate 1 Hour from NYC!
- Peaceful Light-Filled Guesthouse 1 Hour From NYC
- ✔️ Couples escapesn✔️ Family gatheringsn✔️ Private retreatsn✔️ Celebration stays
- The West Lane Inn - Double Queen Room
- Gorgeous Westchester Home with Pool, Hot Tub, Steam Room & Tennis!
- Mountain Vista Luxury Retreat!
- The West Lane Inn - Deluxe Fireplace King
- The West Lane Inn - King Room
- West Lane Inn
- 4 Seasons By The Lake
2. Which vacation homes in Lewisboro are best for families?
If you are looking for a family-friendly vacation home in Lewisboro, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Lewisboro:
3. How many Rentbyowner vacation rentals are available in Lewisboro?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 42 in the Lewisboro area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Lewisboro.
4. What is the cancellation policy for vacation rentals in Lewisboro, New York?
Cancellation policies vary by property, so it’s best to review the specific listing details or contact the owner directly to understand the options and any applicable fees.
5. How do I find the most suitable vacation rental in Lewisboro near popular attractions?
You can filter search results based on your preferred amenities, price range, and location within the area to find a vacation rental that best fits your needs.
6. Are there any additional fees I should be aware of when booking vacation accommodations here?
Additional fees such as cleaning, service charges, or security deposits are typically specified in the listing. Always check the detailed property description or contact the owner for clarification.
7. What safety measures are in place for vacation rentals in Lewisboro?
Safety features and protocols are outlined in each listing, including information about secure entrances, smoke detectors, and other safety equipment; confirm these details with the property owner if needed.
8. How can I confirm the availability of my desired vacation rental in this region?
Availability can be checked through the booking platform by entering your travel dates and contacting the owner if necessary to ensure the property is reserved for your stay.
Lewisboro Top Rated Vacation Rentals
House
10.0(20 Reviews)
3 Bedrooms
1 Bath
5 Guests
1800 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $470/Night
7 Nights - US $3,287
House
4.7(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
2100 ft²
- Private Pool
- Pool
- Pet Friendly
- Kitchen
US $716/Night
7 Nights - US $5,012
House
4 Bedrooms
5 Baths
8 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,000/Night
7 Nights - US $7,000
House
3 Bedrooms
3 Baths
6 Guests
2099 ft²
- Pool
- Kitchen
- Air Conditioner
- Child Friendly
US $549/Night
7 Nights - US $3,843
House
2 Bedrooms
2 Baths
6 Guests
2000 ft²
- Hot Tub
- Fireplace/Heating
- Pool
Lake View
US $458/Night
7 Nights - US $3,206
House
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $296/Night
7 Nights - US $2,070
