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Vacation rentals in Wingdale

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Top-rated vacation rentals in Wingdale

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

Apartment in Kent
Loft 22
Apartment/loft located above the garage in a private home. Set in the rolling hills of Kent, this 2 bedroom loft is cozy enough for anyone looking to explore this quaint little town. Sleeps 3 comfortably. Centrally located to all three private schools. 11 minute drive to Harlem Valley/Wingdale (NY) train station. *Pool is not solely for the use of the Air BNB. *Dogs on property. All friendly. *IF STAYING IN WINTER MONTHS. You must have 4 Wheel drive vehicle. Driveway/Road is long dirt road.*
$150 per night
Guest suite in Sherman
Cozy Scenic New England country retreat w/ hiking
Cozy and private studio in attached guest house on 3 bucolic acres w/pond. Two free kayaks parked by the lake town beach (only 3 miles away). Self check-in with private entrance. Enjoy scenic views of pond and farms from deck & patio with your own grill & fire pit. Mosey or bike (2 bikes provided) along our scenic road to nature preserve. 3 miles to quaint town with restaurants & coffee. Close to Appalachian trail & other great hiking. Pets welcome. Inquire about min stay requirements.
$114 per night
Cabin in Sherman
The Cove Cabin
An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, SUP, two inflatable two person kayaks, and two wooden boats are available for use.
$314 per night

Other great vacation rentals in Wingdale

Home in Pawling
Appalachian Trail House! Easy access to NYC trains
$148 per night
Cabin in Pawling
Serene, Peaceful Cabin by the Lake
$225 per night
Cottage in Kent
NEW - Hot Tub - Mohawk Mtn - Appalachian Trl
$87 per night
Cabin in New Fairfield
The Little Lake Cabin— hot tub, fire pit, & kayaks
$261 per night
Apartment in Dover Plains
*The Ridge House*
$160 per night
Farm stay in Kent
(°) The Wandering Peacock (°)
$279 per night
Apartment in Millbrook
The Haley Cabin
$150 per night
Home in Cornwall
Secluded modern forest cabin with private brook
$196 per night
Home in Carmel Hamlet
Lux Bungalow on the Lake
$187 per night
Guesthouse in New Milford
Luxury in the Litchfield Hills
$230 per night
Cottage in Pawling
Twin Lakes Designer A-frame Stone Cottage
$299 per night
Guest suite in Pawling
Charming Private Studio Apartment Retreat
$158 per night

Destinations to explore

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  2. United States
  3. New York
  4. Dutchess County
  5. Wingdale