Wingdale Vacation Rentals, Houses & More


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1 / 29

Lake House Rental On Your Own Private Lake

  • 4
  • 11
  • 4 nights min

$625

Details

Great rentals within 30 miles that match your search

1 / 21

Private Lakefront & Pool DeeLuxGlamping. NYC Getaway

  • 2
  • 12
  • Min stay varies

$157

Details

11
1 / 73

Pawling 1900 house near Darryl house,Thunder ridge

  • 3
  • 6
  • 2 nights min

$174

Details

9
1 / 20

Lake Bliss the Perfect Getaway

  • 3
  • 10
  • 1 night min

$250

Details

1 / 20

Frank Lloyd Wright Retreat with Outdoor Pool on 8 Secluded Acres

  • 2
  • 3
  • 2 nights min

$459

Details

4
1 / 24

20'x40' inground private pool just for you&house with 4bedrooms

  • 4
  • 8
  • 7 nights min

$286

Details

1 / 14

Lake Cottage with Views and Fireplace

  • 2
  • 5
  • 2 nights min

$199

Details

1 / 20

Five Bedroom Country Home

  • 5
  • 10
  • 3 nights min

$475

Details

2
1 / 8

Beautiful Family Farm in the Heart of Hunt Country, Millbrook NY

  • 5
  • 10
  • 2 nights min

$750

Details

1 / 4

Exclusive Rental in Beautiful Amenia!

  • 3
  • 6
  • 30 nights min

$134

Details

1 / 20

LAKEFRONT COTTAGE ON PRISTINE LAKE

  • 2
  • 4
  • 7 nights min

$225

Details

1 / 24

NEW! 3BR New Preston Cottage - Lakefront w/ Dock!

  • 3
  • 6
  • Min stay varies

$256

Details

1
1 / 23

Rhubarb Hill, a Charming 1850's Farmhouse

  • 3
  • 6
  • 3 nights min

$250

Details

1 / 6

Charming Cottage in a lovely lake community

  • 2
  • 4
  • 7 nights min

$200

Details

1 / 16

Charming Brick House -Hudson Valley

  • 3
  • 7
  • 2 nights min

$325

Details

1 / 25

‘Carriage House’ Lakefront Warren 7BR on 25 Acres!

  • 7
  • 16
  • 4 nights min

$795

Details

1 / 26

Beautiful Streamside Cottage in Dutchess County

  • 2
  • 8
  • 2 nights min

$250

Details

1 / 35

NEW! Cozy Fishkill Studio - Walk to Downtown!

  • Studio
  • 2
  • Min stay varies

$115

Details

1 / 19

Converted Barn on 5+ Acres. WiFi & Serenity.

  • 4
  • 6
  • 7 nights min

$279

Details

1 / 24

NEW! Historic 3BR Home in Fishkill w/ Private Yard

  • 3
  • 10
  • 3 nights min

$300

Details

1 / 14

House on Top of the Hill

  • 3
  • 5
  • 7 nights min

$100

Details

1 / 24

Exceptional Beauty on the Water! House Sleeps 6 Wifi, Hot Tub, billiards

  • 3
  • 6
  • 14 nights min

$515

Details

1 / 57

Hudson Valley Villa - Modern Masterpiece Cantilevered Over Hudson River Bluff

  • 4
  • 8
  • 3 nights min

$1369

Details

1 / 30

South Street 4-BR Cottage with Heated Pool

  • 4
  • 8
  • Min stay varies

$696

Details

1 / 32

New! 3BR Cornwall Bridge Villa w/Spa & Indoor Pool

  • 3
  • 7
  • Min stay varies

$650

Details

1
1 / 35

Restful Rhinebeck cottage

  • 1
  • 4
  • 3 nights min

$120

Details

1 / 15

Nature Lovers Getaway

  • 3
  • 6
  • 7 nights min

$150

Details

1 / 28

Hudson Valley Cabin - Romantic & Secluded Log Cabin with Private Lake - 85 acres

  • 1
  • 2
  • 2 nights min

$225

Details

1 / 21

Harley's Hideaway, A Relaxing Escape

  • 1
  • 2
  • 1 night min

$140

Details

1 / 22

Woodland House - sleeps 10 in luxury

  • 5
  • 10
  • Min stay varies

$499

Details

1 / 17

Sun-Filled House & Yard Near Rhinebeck

  • 4
  • 6
  • 3 nights min

$265

Details

1 / 21

Prana Residence - Spa

  • 3
  • 7
  • 2 nights min

$750

Details

1
1 / 29

Secluded Country Getaway

  • 2
  • 6
  • 2 nights min

$100

Details

1 / 1

Base Camp - Dutch Colonial Estate

  • 1
  • 2
  • 2 nights min

$225

Details

1 / 21

Lovely Victorian Jacuzzi Spa, Walk to Town, Train to NYC

  • 3
  • 4
  • 2 nights min

$189

Details

1 / 19

Historic Heartsease Mansion on Hudson River!

  • 7
  • 13
  • 2 nights min

$1800

Details

12
1 / 18

Hudson Valley 40 Acres With Lake And Hiking

  • 4
  • 12
  • Min stay varies

$550

Details

1 / 7

Chic Beacon Bungalow 3 Blocks Off Main St

  • 3
  • 7
  • 7 nights min

$390

Details

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