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Vacation rentals in Lewisboro

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Top-rated vacation rentals in Lewisboro

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest suite in Wilton
Serene Pond Views charming private patio…
Country Charm Awaits. 45 miles north of George Washington Bridge. Our 2 room efficacy apartment w. microwave, mini fridge & private entrance + parking space. Great WiFi, Apple TV. Enjoy views overlooking Henderson Pond. 1/4 walk to Query State Park, 36 acres w. trails. Our apartment is 4 miles from town of Ridgefield, 3 miles from Wilton town center, 6 miles from New Caanan & 8 miles from Westport Town Center. We have a couple of small puppies who will welcome you too. So we don’t allow pets…
$93 per night
Cottage in Bedford
Clover Cottage
Our beautiful cozy cottage has lots of character and charm: stone foundation, old stone fireplace, cedar shingle roof and large eat-in kitchen. Large living room with french doors opening to a sizable deck. Upstairs is a bedroom with a king bed and bathroom. The best feature of the cottage is the location: we are right in Bedford Village - guests can walk to restaurants, shops, the Bedford Playhouse, the library and post office. Located 10 minutes from Metro-north and a 1-hr drive from NYC.
$189 per night
Cottage in South Salem
Private cottage in horse country &1 hour from NYC!
Private cozy cottage located in horse country on the the NY/CT borders ( New Canaan, Ridgfield, Wilton ) It is a perfect quiet getaway for couples or a friends night out , a great pit stop for travelers /skiers , fine dining , shopping /antiquing , Ridgefield Playhouse , hiking ,and a short ride to Grace Farms . 1 hour train ride to NYC . We provide organic fruit,breakfast snacks, coffee and tea . It is your home away from home and more :)
$198 per night

Stay near Lewisboro's top sights

Photo of Ridgefield Playhouse
Ridgefield Playhouse32 locals recommend
Photo of King Kone
King Kone11 locals recommend
Photo of The Inn at Pound Ridge
The Inn at Pound Ridge47 locals recommend
Photo of Muscoot Tavern
Muscoot Tavern10 locals recommend
Photo of Prospector Theater
Prospector Theater15 locals recommend
Photo of Bareburger
Bareburger13 locals recommend

Other great vacation rentals in Lewisboro

Rental unit in Pound Ridge
The Suite at Pound Ridge
$199 per night
Private room in Katonah
Sweet Suite, walk to train and Katonah
$101 per night
Rental unit in Mount Kisco
Cozy 1 Bdrm Apt; Privt Entry; 5 min walk to train
$125 per night
Private room in Danbury
Private Room - Danbury
$50 per night
Guesthouse in South Salem
Newly renovated 1-bedroom guesthouse
$250 per night
Barn in Mount Kisco
NY Rustic Cottage Getaway
$132 per night
Private room in Danbury
Contemporary Peaceful Home in Great Location!
$45 per night
Private room in Bethel
Comfortable Room in Historic Bethel Queen Bed.
$50 per night
Private room in Danbury
Getaway Room
$53 per night
Private room in Croton-on-Hudson
Comfortable Bedroom + Bathroom with Parking
$87 per night
Private room in Pound Ridge
Adirondacks in Westchester 2
$105 per night
Private room in Mount Kisco
Easterly suite in large house
$96 per night
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