Sleepy Hollow Vacation Rentals

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Vacation Rentals in Sleepy Hollow

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Greenwich CT

$216 nightly

$245 total

Dec 9 - Dec 10

Total with taxes and fees

With a stay at this vacation home in Greenwich, you'll be within a 15-minute drive of E. Gaynor Brennan Golf Course and Yale New Haven Health Long Ridge Medical Center.

Kitchen

Free WiFi

Contemporary Cozy Cottage

Lake Peekskill NY

$367 nightly

$420 total

Dec 9 - Dec 10

Total with taxes and fees

With a stay at this vacation home in Lake Peekskill, you'll be within a 15-minute drive of Regal UA Cortlandt Town Center and Hudson Valley Center for Contemporary Art.

Kitchen

Washer

Spacious Harlem Brownstone Garden 2-Bedroom Apartment with a large rear yard,

New York NY

$346 nightly

$378 total

Jan 7 - Jan 8, 2026

Total with taxes and fees

With a stay at this vacation home in New York (Manhattan), you'll be within a 5-minute drive of Central Park and Yankee Stadium.

Kitchen

Free WiFi

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

New Rochelle NY

With a stay at this vacation home, you'll be centrally located in New Rochelle, within a 10-minute drive of NewYork-Presbyterian - Westchester Hospital and Iona College.

Kitchen

Free WiFi

Spacious 4-bedroom house in charming Rye with AC

Rye NY

$2,499 nightly

$2,499 total

Dec 9 - Dec 10

Total with taxes and fees

Located in Rye, Spacious 4-bedroom house in charming Rye with AC is a 5-minute drive from Rye Playland and 6 minutes from Emelin Theatre.

Pet friendly

Air conditioning

Marvelous 5-bedroom house with AC in Yonkers

Yonkers NY

With a stay at this vacation home in Yonkers (Bryn Mawr), you'll be within a 15-minute drive of Yankee Stadium and NewYork-Presbyterian - Westchester Hospital.

Washer

Dryer

Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.

Nyack NY

Located in Nyack, this vacation home is within a 15-minute walk of Edward Hopper House Art Center and Nyack Hospital.

Washer

Dryer

Ultra-Modern Luxe Sleek & Stunning Stay

White Plains NY

With a stay at this vacation home in White Plains, you'll be within a 15-minute drive of NewYork-Presbyterian - Westchester Hospital and The Westchester Mall.

Kitchen

Washer

Cozy 2 Bedroom, Near NYC, Easy Parking

Yonkers NY

With a stay at this vacation home in Yonkers (Bryn Mawr), you'll be within a 15-minute drive of Yankee Stadium and NewYork-Presbyterian - Westchester Hospital.

Kitchen

Pet friendly

La Casita Bonita near NYC

Yonkers NY

With a stay at this vacation home in Yonkers (Bryn Mawr), you'll be within a 15-minute drive of Yankee Stadium and NewYork-Presbyterian - Westchester Hospital.

Kitchen

Washer

Stylish Beach Home near Stamford Downtown/Beach

Stamford CT

$686 nightly

$729 total

Dec 11 - Dec 12

Total with taxes and fees

A stay at this vacation home places you in the heart of Stamford, within a 5-minute drive of Cove Island Park and Chelsea Piers.

Kitchen

Washer

New Jersey home, close to NY City Fun!

Englewood NJ

Located in Englewood, this vacation home is within a 15-minute drive of American Dream and Yankee Stadium.

Kitchen

Washer

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.