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Vacation Rentals & Villas in Wingdale

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37 Houses

Lake House Rental On Your Own Private Lake

Wingdale villa

4 bedrooms / 3 bathrooms / sleeps 11

Price per night from

$726

Great rentals within 20 miles that match your search

Quiet Country Contemporary Home – Ideal Respite From The City

West Cornwall house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$430

2 Bedroom Suite with Kitchen

Roxbury hotel apartment

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$287

Exclusive Rental in Beautiful Amenia!

Amenia house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$153

The FarmHouse

Millerton house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$288

1790 Classic Colonial Center Hall home

Sharon house

5 bedrooms / 3 bathrooms / sleeps 11

Price per night from

$805

Kent Victorian Room 1

Kent private room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$183

Kent Victorian Room 3

Kent private room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$172

Tentrr - Cooke's Creek

East Fishkill tented camp

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$160

Serene haven in the country

Washington house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$552

Charming Brick House -Hudson Valley

Poughkeepsie house

3 bedrooms / 1 bathroom / sleeps 7

Responds fast! avg. 1 hour 47 minutes

Price per night from

$458

Night Light Lake House

New Fairfield house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$389

Kent Victorian Room 2

Kent private room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$173

Kent Victorian Room 5

Kent private room

2 bedrooms / 1 bathroom / sleeps 3

Price per night from

$184

Kent Victorian Room 4

Kent private room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$128

Tentrr Signature Site - Holmestead Woods

Southeast tented camp

1 bedroom / 1 bathroom / sleeps 8

Responds fast! avg. 3 hours 30 minutes

Price per night from

$104

Tentrr Signature Site - Driftways Farm

Millerton tented camp

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 30 minutes

Price per night from

$144

Tentrr Signature Site - A Riverwalk

Stanfordville tented camp

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 30 minutes

Price per night from

$144

Tentrr Signature Site - Private Peaceful Farm Venture

Bangall tented camp

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 30 minutes

Price per night from

$132

Tentrr Signature Site - Creekside Solitude

Clinton Corners tented camp

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 30 minutes

Price per night from

$98

Dainty New Preston Cottage w/ Dock & Lake Views!

New Preston cottage

3 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 23 minutes

Price per night from

$247

Tentrr Signature Site - Hudson Valley Hilltop 1

Pine Plains tented camp

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 30 minutes

Price per night from

$194

NEW! Enchanting Hudson Valley Farmhouse w/ Views!

Salt Point house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 23 minutes

Price per night from

$320

Prana Residence - Spa

Cornwall Bridge house

3 bedrooms / 3 bathrooms / sleeps 7

Price per night from

$860

Harley's Hideaway, A Relaxing Escape

Stanfordville apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$161

Tentrr Signature Site - Hudson Valley Hilltop 2

Pine Plains tented camp

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 30 minutes

Price per night from

$194

Sherman Home w/Lakefront Deck & Swimming Dock

Sherman house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 23 minutes

Price per night from

$726

NEW! Whimsical Cottage in Washington w/ Fire Pit!

Washington Depot cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 23 minutes

Price per night from

$277

NEW! Secluded Home w/Fire Pit: Sip, Ski & Explore!

Salt Point house

6 bedrooms / 2 bathrooms / sleeps 11

Responds fast! avg. 2 hours 23 minutes

Price per night from

$178

Sunset Manor

Mahopac Falls house

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$860

Family Getaway w/ Fireplace in Sherman on 4 Acres!

Sherman house

7 bedrooms / 5 bathrooms / sleeps 16

Responds fast! avg. 2 hours 23 minutes

Price per night from

$887

NEW! Chic & Spacious Riverfront Reprieve w/ Dock!

Bridgewater house

6 bedrooms / 5 bathrooms / sleeps 17

Responds fast! avg. 2 hours 23 minutes

Price per night from

$939

NEW! Modern Home w/ Views By Hudson Valley Hiking

Stormville house

5 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 2 hours 23 minutes

Price per night from

$290

NEW! 2,438 Sq Ft Washington House - Pets Welcome!

Washington Depot cottage

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 23 minutes

Price per night from

$377

Dutchess County Guest House on Working Horse Farm!

Salt Point house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 23 minutes

Price per night from

$296

Newly Listed Lake House! Private Beach on Candlewood Lake, New Construction Beau

New Fairfield house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$115

Tentrr Signature Site - Maybrook Farm - The Ridge

Poughquag tented camp

1 bedroom / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 30 minutes

Price per night from

$114

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