Vacation Rentals & Villas in Wingdale

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37 Houses

29

Lake House Rental On Your Own Private Lake

New York / Wingdale

Wingdale villa

4 11 4 nights min

  • 4 bedrooms
  • sleeps 11
  • 4 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$625

Price per night from

$625

Great rentals within 20 miles that match your search

Distance approx 12.13 km from Wingdale

32

Lake House with Indoor Spa, 1 hour from Manhattan

New York / Carmel

Carmel house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly

Price per night from

$200

Price per night from

$200

Distance approx 13.66 km from Wingdale

30

South Street 4-BR Cottage with Heated Pool

Connecticut / Washington

Washington house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$696

Price per night from

$696

Distance approx 15.38 km from Wingdale

24

Prana Residence - Spa

Connecticut / Cornwall Bridge

Cornwall Bridge house

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$751

Price per night from

$751

Distance approx 19.65 km from Wingdale

28

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

New York / Stanfordville

Stanfordville log cabin

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

Price per night from

$225

Price per night from

$225

Distance approx 12.39 km from Wingdale

24

Unique New Fairfield House w/ Deck & Lake Views!

Connecticut / New Fairfield

New Fairfield house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$250

Responds fast!
avg. 27 minutes

Price per night from

$250

Distance approx 10.04 km from Wingdale

8

Large Private Apartment

New York / Verbank

Verbank apartment

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child Friendly

Price per night from

$100

Price per night from

$100

Distance approx 19.17 km from Wingdale

19

Harley's Hideaway, A Relaxing Escape

New York / Stanfordville

Stanfordville apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 20 mi
  • Air conditioning
  • Private garden

Price per night from

$140

Price per night from

$140

Distance approx 18.17 km from Wingdale

26

Beautiful Streamside Cottage in Dutchess County

New York / Clinton Corners

Clinton Corners house

2 8 2 nights min

  • 2 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Child Friendly

Price per night from

$250

Price per night from

$250

Distance approx 8.51 km from Wingdale

14

Lake Cottage with Views and Fireplace

Connecticut / Sherman

Sherman house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$199

Responds fast!
avg. 1 hour 16 minutes

Price per night from

$199

Distance approx 10.19 km from Wingdale

20

Frank Lloyd Wright Retreat with Outdoor Pool on 8 Secluded Acres

New York / LaGrangeville

LaGrangeville house

2 3 2 nights min

  • 2 bedrooms
  • sleeps 3
  • 2 nights min

Price per night from

$699

Price per night from

$699

Distance approx 7.83 km from Wingdale

(9) Very Good 

20

Lake Bliss the Perfect Getaway

New York / Holmes

Holmes house

3 10 1 night min

  • 3 bedrooms
  • sleeps 10
  • 1 night min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$250

Price per night from

$250

Distance approx 11.41 km from Wingdale

24

Lakefront New Preston Cottage w/Dock & Fire Pit!

Connecticut / New Preston

New Preston cottage

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$200

Responds fast!
avg. 38 minutes

Price per night from

$200

Distance approx 7.68 km from Wingdale Show on Map

(4) Excellent 

36

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

Connecticut / New Milford

New Milford house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 13 mi
  • Swimming pool
“Wonderful experience!!!” My wife and our two children (10 and 7)spent a wonderful time at this beautiful New Milford retreat. The house was spacious and nicely decorated and we loved the privacy of the place. You couldn't see any neighbors and yet sho
…see more

Price per night from

$286

Responds fast!
avg. 1 hour 37 minutes

Price per night from

$286

Distance approx 17.75 km from Wingdale

(1) Excellent 

16

Wits End Farm

Connecticut / Bethlehem

Bethlehem house

6 12 3 nights min

  • 6 bedrooms
  • sleeps 12
  • 3 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child Friendly

Price per night from

$899

Price per night from

$899

Distance approx 19.28 km from Wingdale

16

Charming Brick House -Hudson Valley

New York / Poughkeepsie

Poughkeepsie house

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$300

Price per night from

$300

Distance approx 17.75 km from Wingdale

(1) Excellent 

14

Wits End Farm B&B

Connecticut / Bethlehem

Bethlehem b and b

5 10 4 nights min

  • 5 bedrooms
  • sleeps 10
  • 4 nights min
  • Child Friendly

Price per night from

$799

Price per night from

$799

Distance approx 18.71 km from Wingdale

19

Converted Barn on 5+ Acres. WiFi & Serenity.

New York / Clinton Corners

Clinton Corners house

4 6 7 nights min

  • 4 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly

Price per night from

$279

Price per night from

$279

Distance approx 18.79 km from Wingdale

12

The FarmHouse

New York / Millerton

Millerton house

2 5 120 nights min

  • 2 bedrooms
  • sleeps 5
  • 120 nights min

Price per night from

$93

Price per night from

$93

Distance approx 18.97 km from Wingdale

13

Quiet Country Contemporary Home on 5 Private Acres

Connecticut / West Cornwall

West Cornwall house

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Nearest beach 6 mi
  • Child Friendly
  • Air conditioning

Price per night from

$405

Price per night from

$405

Distance approx 7.55 km from Wingdale Show on Map

8

Kent Victorian Room 4

Connecticut / Kent

Kent room

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$110

Price per night from

$110

Distance approx 16.08 km from Wingdale

44

1790 Classic Colonial Center Hall home

Connecticut / Sharon

Sharon house

5 11 min stay varies

  • 5 bedrooms
  • sleeps 11
  • min stay varies
  • Child Friendly

Price per night from

$500

Price per night from

$500

Distance approx 11.38 km from Wingdale

(1) Excellent 

23

Rhubarb Hill, a Charming 1850's Farmhouse

Connecticut / New Preston

New Preston house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Car not necessary
  • Pet Friendly

Price per night from

$350

Price per night from

$350

Distance approx 7.55 km from Wingdale Show on Map

8

Kent Victorian Room 3

Connecticut / Kent

Kent room

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$149

Price per night from

$149

Distance approx 7.55 km from Wingdale Show on Map

8

Kent Victorian Room 2

Connecticut / Kent

Kent room

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$149

Price per night from

$149

Distance approx 16.85 km from Wingdale

25

Dutchess County Guest House on Working Horse Farm!

New York / Salt Point

Salt Point house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$280

Responds fast!
avg. 27 minutes

Price per night from

$280

Distance approx 12.2 km from Wingdale

25

Lakefront Warren 'Carriage House' on 25 Acres!

Connecticut / Warren

Warren house

7 14 4 nights min

  • 7 bedrooms
  • sleeps 14
  • 4 nights min
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$1,001

Responds fast!
avg. 22 minutes

Price per night from

$1,001

Distance approx 7.8 km from Wingdale Show on Map

29

Very private,4bdrm house,20x40inground pool, pool house. Paradise!

Connecticut / New Milford

New Milford house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly

Price per night from

$350

Price per night from

$350

Distance approx 7.55 km from Wingdale Show on Map

8

Kent Victorian Room 5

Connecticut / Kent

Kent room

2 3 2 nights min

  • 2 bedrooms
  • sleeps 3
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$159

Price per night from

$159

Distance approx 6.12 km from Wingdale Show on Map

(1) Excellent 

31

Private Lakefront & Pool DeeLuxGlamping. NYC Getaway

New York / Pawling

Pawling camper van

2 8 1 night min

  • 2 bedrooms
  • sleeps 8
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$157

Price per night from

$157

Distance approx 19.58 km from Wingdale

24

Charming Hudson Valley Studio - Walk to Downtown!

New York / Fishkill

Fishkill studio

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$115

Responds fast!
avg. 22 minutes

Price per night from

$115

Distance approx 7.55 km from Wingdale Show on Map

6

Kent Victorian Room 1

Connecticut / Kent

Kent room

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning
  • Private garden

Price per night from

$159

Price per night from

$159

Distance approx 13.87 km from Wingdale

4

Exclusive Rental in Beautiful Amenia!

New York / Amenia

Amenia house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$133

Price per night from

$133

Distance approx 10.83 km from Wingdale

(1)  

32

Must Love Garden and the Sound of Stream

New York / Lanesville

Lanesville house

4 9 1 night min

  • 4 bedrooms
  • sleeps 9
  • 1 night min
  • Child Friendly
  • Pet Friendly

Price per night from

$250

Price per night from

$250

Distance approx 19.81 km from Wingdale

(3) Very Good 

22

Comfortable Rustic Cottage on 4 Wooded Acres with Brook

Connecticut / West Cornwall

West Cornwall cottage

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 12 mi
  • Child Friendly
  • Air conditioning

Price per night from

$150

Price per night from

$150

Distance approx 16.68 km from Wingdale

20

LAKEFRONT COTTAGE ON PRISTINE LAKE

New York / Carmel

Carmel cottage

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Ask about children
  • Air conditioning

Price per night from

$225

Price per night from

$225

Distance approx 16.09 km from Wingdale

7

2 Bedroom Suite with Kitchen

Connecticut / Roxbury

Roxbury hotel apartment

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$249

Price per night from

$249