Vacation rentals in Wingdale

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Top-rated holiday rentals in Wingdale

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

Superhost
Cabin in Pawling
Serene, Peaceful Cabin by the Lake
Take a stroll down to the lake in the crisp morning air, then light the fire and sink into the cherry leather armchair at this rustic log cabin. Touches of soft sage add a soothing side, while patterned rugs and chunky beams keep things homey. Authentic Log cabin, private lake with swimming, kayaking --1000's acres adjacent private land, fishing, hunting-- Enjoy the harvest of the Hudson Valley-- minutes to wineries, Pawling train to NYC, Appalachian trail and hiking, Child safe. Minutes walk to Lake! Private Lake-- We are here to check you in and only if you need us. We respect your privacy and "time-away". The property sits in a private, sprawling lake community minutes from wineries for tastings, Pawling station for trains to New York City, and the Appalachian trail for scenic hiking. Explore Wallkill and Warwick within around an hour's drive. Car, Metro North (train to NYC), Uber, Lyft...
2–9 Apr
$427 NZD per night
4.95 out of 5 average rating, 110 reviews
Guest favourite
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.*
7–14 Nov
$275 NZD per night
4.93 out of 5 average rating, 127 reviews
Guest favourite
Home in Danbury
BEAUTIFUL PRIVATE APARTMENT SUITE IN DANBURY CT!!
Private 1100 sq. Ft. suite staycation located in a beautiful, safe, quiet neighborhood in DanburyModern Kitchen, One Bathroom, One Luxury Queen Size Bed, 55” Smart TV with Cable/Amazon Prime/Netflix, Apple Cable charger next to bed, Wi-Fi, AC, Heat, Refrigerator, Countertop Oven, Microwave, Electric Hot Plate, Keurig Coffee Maker, Hair Dryer, Iron, Ironing Board, Shampoo, Conditioner, Body Wash. The space is nonsmoking inside and outside the premises including vaping. No children or infants
2–9 Feb
$277 NZD per night
4.99 out of 5 average rating, 335 reviews

Popular amenities for Wingdale holiday rentals

Other great holiday rentals in Wingdale

Guest favourite
Farm stay in Ancram
Relaxing secluded stay with loving social animals.
7–14 Oct
$262 NZD per night
4.95 out of 5 average rating, 257 reviews
Guest favourite
Home in Stormville
Private Hudson Valley Country Retreat
9–16 Jan
$1,411 NZD per night
4.94 out of 5 average rating, 156 reviews
Guest favourite
Home in Rhinebeck
Architectural wonder in the woods
14–21 Jun
$959 NZD per night
4.91 out of 5 average rating, 253 reviews
Guest favourite
Home in Pawling
Hobbit House of Pawling
26 Jul – 2 Aug
$1,005 NZD per night
5.0 out of 5 average rating, 184 reviews
Guest favourite
Guest suite in Kent
Bright 1-bedroom in walking distance to town
20–27 Mar
$236 NZD per night
5.0 out of 5 average rating, 52 reviews
Guest favourite
Apartment in Amenia
Amenia Main St Cozy Studio
30 Jun – 7 Jul
$139 NZD per night
5.0 out of 5 average rating, 17 reviews
Superhost
Home in Dover Plains
5 Harts Rd - Newly built home in Dover, NY
24–31 May
$253 NZD per night
4.91 out of 5 average rating, 33 reviews
Guest favourite
Guesthouse in Dover Plains
Spilt Milk Cottage - Hudson Valley, NY
12–19 Jul
$219 NZD per night
4.88 out of 5 average rating, 82 reviews
Guest favourite
Guesthouse in Sharon
Cottage with a Waterfall View
3–10 May
$200 NZD per night
5.0 out of 5 average rating, 58 reviews
Guest favourite
Home in Dover Plains
Somewhere That’s Green, Gameroom/Bar, Fenced yard
14–21 Feb
$676 NZD per night
5.0 out of 5 average rating, 24 reviews
Guest favourite
Guesthouse in New Milford
Luxury in the Litchfield Hills
20–27 Sep
$390 NZD per night
5.0 out of 5 average rating, 40 reviews
Guest favourite
Home in Pawling
Country Village Getaway
26 Oct – 2 Nov
$283 NZD per night
4.95 out of 5 average rating, 21 reviews

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