What are the top rated Cottage 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 Cottage Rentals in Lewisboro: <a href="/property/serenity-with-pool-in-pound-ridge-ny/HA-3212184824" class="class="static-page-link"">Serenity with Pool in Pound Ridge, NY</a> <a href="/property/mid-century-modern-getaway-only-1hr-from-the-city/HA-3213249884" class="class="static-page-link"">Mid- Century Modern getaway - only 1hr from the city!</a> <a href="/property/poolside-paradise-luxe-5-bedroom-w-peloton-gym/HA-3212701585" class="class="static-page-link"">Poolside Paradise: Luxe 5-Bedroom w/Peloton Gym</a> <a href="/property/picturesque-south-salem-lakehouse-w-pool-yard/HA-1219622242" class="class="static-page-link"">Picturesque South Salem Lakehouse w/ Pool &amp; Yard!</a> <a href="/property/english-cottage-and-gardens-in-pound-ridge/HA-3212949362" class="class="static-page-link"">English Cottage and Gardens in Pound Ridge</a> <a href="/property/large-lakehouse-fishing-kayaking-heated-pool-fireplaces-multiple-bedrooms/HA-3213695751" class="class="static-page-link"">Large lakehouse, fishing, kayaking, heated pool, fireplaces multiple bedrooms!</a> <a href="/property/private-colonial-oasis-for-summer-2022-heated-saltwater-pool-hot-tub-office/HA-3212186286" class="class="static-page-link"">Private colonial oasis for Summer 2022 : heated saltwater pool, hot tub, office</a> <a href="/property/3-bedroom-lakefront-house-w-pool-lakeside-dock-sunset-views/HA-3214468907" class="class="static-page-link"">3-bedroom Lakefront House w/Pool, Lakeside Dock, Sunset Views</a> <a href="/property/the-west-lane-inn-family-suite-with-kitchenette/HA-3212001876" class="class="static-page-link"">The West Lane Inn - Family Suite with Kitchenette</a> <a href="/property/historic-summer-cottage-close-to-private-beach-for-rent-by-the-month-or-week/HA-3211631665" class="class="static-page-link"">Historic Summer cottage, close to private beach for rent by the month or week</a>

How much does it cost to rent a cottage in Lewisboro?

The average cost for a cottage rental in Lewisboro is $588 per night. Lakesresorts has a wide list of great cottages near Lewisboro that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Lewisboro that allow pets?

Yes, here are the top cottage rentals in Lewisboro that allow you to bring your pet: Peaceful Light-Filled Guesthouse 1 Hour From NYC Mountain Vista Luxury Retreat! West Lane Inn Rain, Snow, or Shine! Fun, Comfort, and Luxury await inside. <a href="/all/usa/new-york/lewisboro" class="class="static-page-link"">See all pet-friendly vacation rentals in Lewisboro on Lakesresorts</a>

Do you have any rental cottages in Lewisboro that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Lewisboro to find one that works for you.

Are there quality cottages in Lewisboro that have indoor swimming pools?

As of 2026, the data from Lakesresorts shows that there are Over 43 private swimming pools or cottages with indoor pools in the Lewisboro area along with other great amenities.

Lewisboro Cottage Rentals By Owner

Peaceful Light-Filled Guesthouse 1 Hour From NYC

From US $850

10.0 (9 Reviews)

House

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Air Conditioner
Parking
Pool

Lewisboro Cottage Rentals & Holiday Homes

Find the best cottages in Lewisboro - We found 43 exact matches

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