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Vacation rentals in Chappaqua

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Top-rated vacation rentals in Chappaqua

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

Home in Armonk
Bucolic 3 Bed/2 Bath Cottage On 2+ Lush Acres
Welcome to Long House Farm! Take it easy at this serene getaway, situated on 2+ acres including a meadow, old growth maple and spruce trees, and adjacent to two acres of protected beautiful wetlands. Once an old dairy farm, this home has been completely remodeled head to foot and features 3 bedrooms & 2 full bathrooms, front & back patio, HVAC, fully stocked kitchen, and brand new washer/dryer. Other amenities include high speed internet, two TVs and full cable package. *No Walk-throughs.
$200 per night
Private room in Mount Kisco
Easterly suite in large house
Easterly suite in large house on private 4 acre property. Plenty parking space. A great getaway suite in a perfectly situated Westchester home, just 50 minutes away from New York City. Kindly note that we request photo ID documents to be presented upon check-in from all adults in your party. We request detailed, verifiable information from new member guests with zero feedback, and/or applicants under age of 25. Due to Covid 19, our kitchen access is limited now.
$96 per night
Private room in Ossining
Freshly updated room
Nicely renovated and clean room to relax after the day. New full bed, perfect for one. Nice deck to sit and enjoy your morning coffee among the fall foliage. My house is in a quiet family neighborhood. Close to trains, highways, hiking, biking. Shopping, restaurants, and hospitals are nearby too. Car needed. Please no unregistered guests. Quiet time is 10 pm to 6 am. Scheduled showers. There is a half bath in your room. I do have a friendly dog.
$50 per night

Stay near Chappaqua's top sights

Photo of Crabtree's Kittle House Restaurant & Inn
Crabtree's Kittle House Restaurant & Inn6 locals recommend
Photo of Gedney Park
Gedney Park6 locals recommend
Photo of DeCicco & Sons
DeCicco & Sons4 locals recommend
Photo of Lexington Square Cafe
Lexington Square Cafe5 locals recommend
Photo of Hacienda la Paloma
Hacienda la Paloma4 locals recommend
Photo of Craft Pizza & Beer
Craft Pizza & Beer4 locals recommend

Other great vacation rentals in Chappaqua

Private room in Pound Ridge
Adirondacks in Westchester 2
$102 per night
Private room in Armonk
Spacious Room With a View
$56 per night
Private room in Valhalla
Valhalla, NY Pvt Dbl Rm #2 Travel Nurses & NYMC!
$76 per night
Cottage in Valhalla
Charming private 1BR apt. Easy access to NYC
$101 per night
Private room in Armonk
Country Hideaway off Windmill Road.
$56 per night
Barn in Mount Kisco
NY Rustic Cottage Getaway
$135 per night
Rental unit in Mount Kisco
Cozy 1 Bdrm Apt; Privt Entry; 5 min walk to train
$125 per night
Guest suite in Ossining
Comfortable Studio Apartment
$88 per night
Private room in Elmsford
1-1 INSIDE OF new Westchester home
$100 per night
Home in Pleasantville
Beautiful 3 bedroom apt in great location
$175 per night
Earthen home in Ossining
The Babbling Brook
$120 per night
Guest suite in Armonk
Cozy, In Nature
$76 per night
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