Photo by Marina Timo

Holiday Homes in Town of Lewisboro

Compare and save

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sep - 28 Sep

Featured Holiday Homes in Town of Lewisboro

Luxury NY Home with Free Parking
Enjoy cooking in this well-equipped kitchen with a stainless steel range, dishwasher, and double sink.

Luxury NY Home with Free Parking

4.0 star property
Luxury NY Home with Free Parking
479 South Benson
Enjoy a serene beach experience with access to the shore, picnic tables, and a lifeguard tower nearby.

479 South Benson

4.0 star property
479 South Benson
The Inn at Fairfield Beach
Front of property

The Inn at Fairfield Beach

3.0 star property
8.2 out of 10, Very good, (523)
"Best location, good value, stayed there 3 times, will return again "
The Inn at Fairfield Beach
Gorgeous Garrison Gem Pool Sauna Hot Tub More
House | 5 bedrooms

Gorgeous Garrison Gem Pool Sauna Hot Tub More

2.0 star property
Gorgeous Garrison Gem Pool Sauna Hot Tub More
Cozy Private Home W Fireplace Outdoor Kitchen
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel range hood, and appliances.

Cozy Private Home W Fireplace Outdoor Kitchen

2.0 star property
Cozy Private Home W Fireplace Outdoor Kitchen
Garrison Gem Pool Sauna Hot Tub Steam
Relax by the serene pool surrounded by lush greenery and a covered patio with comfortable seating.

Garrison Gem Pool Sauna Hot Tub Steam

2.0 star property
Garrison Gem Pool Sauna Hot Tub Steam
Hudson River Views Firepit Patio Dog Run Game Room Stone Manor
Enjoy cooking in this well-lit kitchen with a large island, stainless steel sink, and ample counter space.

Hudson River Views Firepit Patio Dog Run Game Room Stone Manor

2.0 star property
Hudson River Views Firepit Patio Dog Run Game Room Stone Manor
Whimsical Staycation Fire Pit Full House 2 Bedroom Home by RedAwning
Relax by the fire pit in the serene backyard, surrounded by lush greenery and a wooden deck.

Whimsical Staycation Fire Pit Full House 2 Bedroom Home by RedAwning

3.0 star property
Whimsical Staycation Fire Pit Full House 2 Bedroom Home by RedAwning
Gorgeous Garrison Gem Pool Sauna Hot Tub More
Relax by the pool surrounded by lush gardens and a shaded pergola.

Gorgeous Garrison Gem Pool Sauna Hot Tub More

2.0 star property
Gorgeous Garrison Gem Pool Sauna Hot Tub More
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Town of Lewisboro Hotel Reviews

Baymont by Wyndham White Plains - Elmsford

Baymont by Wyndham White Plains - Elmsford

10/10 Excellent
"Toilet wasn’t working but we got transfer to a different room but other that everything was good"
sonny m 1-night trip
Posted 8 hours ago
Baymont by Wyndham White Plains - Elmsford