Sleepy Hollow Vacations 2026 from CA $992

Sleepy Hollow flight + hotel packages

Price found within the past 48 hours. Click for updated prices.

Hyatt Regency Greenwich

CA $992

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to White Plains (HPN)

Book a stay at this business-friendly hotel in Old Greenwich. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions E. Gaynor Brennan Golf Course and Mianus Park are located nearby.

Delamar Greenwich Harbor

CA $1,385

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to White Plains (HPN)

Book a stay at this beach hotel in Greenwich. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Greenwich Ferry Dock and Bruce Museum of Arts and Science are located nearby.

Hyatus Luxury Residences Stamford

Downtown Stamford

CA $1,305

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to White Plains (HPN)

Book a stay at this luxury aparthotel in Stamford. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Stamford Town Center and Stamford Center for the Arts are located nearby.

Delamar Southport

CA $1,137

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to White Plains (HPN)

Book a stay at this spa hotel in Southport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Sasco Hill Beach and Southport Beach are located nearby.

Delamar Westport

CA $1,030

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to White Plains (HPN)

Stay at this hotel in Westport. Enjoy free breakfast, free valet parking, and free train station pick-up. Popular attractions Southport Beach and Burying Hill Beach are located nearby.

Top Sleepy Hollow hotels deals

Radio Hotel

2420 Amsterdam Ave New York NY

Free cancellation

Reserve now, pay when you stay

CA $262

CA $344 total

Sep 28 - Sep 29

includes taxes & fees

Book a stay at this business-friendly hotel in New York. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Yankee Stadium and Central Park are located nearby.

Pet-friendly

Restaurant

DoubleTree by Hilton Fort Lee - George Washington Bridge

2117 Route 4 Eastbound Fort Lee NJ

Free cancellation

Reserve now, pay when you stay

CA $184

CA $211 total

Oct 26 - Oct 27

includes taxes & fees

Book a stay at this business-friendly hotel in Fort Lee. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Yankee Stadium and Central Park are located nearby.

Tarrytown House Estate

49 E Sunnyside Lane Tarrytown NY

CA $225

CA $293 total

Oct 4 - Oct 5

includes taxes & fees

Book a stay at this business-friendly hotel in Tarrytown. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Lyndhurst Mansion and Westchester County Center are located nearby.

Highbridge Hotel

1263 Edward L Grant Highway Bronx NY

Free cancellation

Reserve now, pay when you stay

CA $191

CA $224 total

Sep 30 - Oct 1

includes taxes & fees

Book a stay at this business-friendly hotel in Bronx. Enjoy free breakfast, free WiFi, and a rooftop terrace. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Yankee Stadium and Central Park are located nearby.

Breakfast included

Free WiFi

Armoni Inn & Suites

329 Route 303 Orangeburg NY

Get rates

Book a stay at this business-friendly hotel in Orangeburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. Popular attractions Lyndhurst Mansion and Tallman Mountain State Park are located nearby.

Westchester Marriott

670 White Plains Rd Tarrytown NY

Free cancellation

Reserve now, pay when you stay

CA $275

CA $315 total

Oct 4 - Oct 5

includes taxes & fees

Book a stay at this spa hotel in Tarrytown. Enjoy free parking, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Westchester County Center and Orange Trailhead are located nearby.

Spa

Parking included

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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.

Stay near popular Sleepy Hollow attractions

A lighthouse and a large bridge with construction cranes.

Tarrytown Lighthouse

8.4/10 (104 reviews)

You can learn about the history of Sleepy Hollow with a stop at Tarrytown Lighthouse. Stroll along the riverfront in this quaint area, or check out its top-notch restaurants.

See properties

Sleepy Hollow Vacations

Even if you're the most impulsive traveler, it's still a wise idea to know a few things about Sleepy Hollow before you go. Have a look at it on the map, investigate its main attractions and let the excitement begin!

Sleepy Hollow is a neighborhood in White Plains. You'll find it 7 miles (11 kilometers) northwest of the downtown area.

White Plains is home to some 57,000 residents.

Places to visit in Sleepy Hollow

Admire ornate tombstones and poetic epitaphs at Sleepy Hollow Cemetery. Need more nearby options? What year was it made and what went on there? Try to find the answers to these questions when visiting Philipsburg Manor, a historically significant building. And that's not all there is. If you'd like to find a little spiritual enlightenment on your travels, stop by Old Dutch Church of Sleepy Hollow. You never know, you may even find the answers to some of life's greatest questions!

Where do you fly into for Sleepy Hollow?

Landing at LaGuardia Airport (LGA)? Sleepy Hollow is just 20 miles (32 kilometers) away. Grab some nibbles, hop in a cab and you'll arrive before you know it!

Frequently asked questions

How much are vacation packages to Sleepy Hollow?

Travelocity offers flight and hotel vacation packages from an incredible CA $992. With such amazing deals, you'll be saying hello to Sleepy Hollow in a flash.

Where can I get the best vacation package deals for Sleepy Hollow?

You'll discover a terrific range of Sleepy Hollow package deals on Travelocity. With as many as 400 airlines and 1,000,000 properties across the globe, piecing together the ultimate escape will be a breeze.

Why should I purchase my Sleepy Hollow vacation bundle with Travelocity?

From incredible destinations to memorable experiences, we have everything you need to satisfy your travel desires. Our friendly 24/7 customer support will also make sure you're being taken care of before, during and after your getaway. And don't fret if you notice a cheaper price on your booking, we'll match it. That's our Price Match Guarantee.

Can I save on my Sleepy Hollow car rental if I book it with hotels and flights?

With a Sleepy Hollow vacation package, you can bundle your flight, car and hotel bookings and save a tidy sum. If you want to discover the best of this impressive destination, why not start with Liberty Bell Center? This top sight is 161 kilometers from Sleepy Hollow. With your own wheels, you'll be there in no time.

Which airport is best for Sleepy Hollow?

John F. Kennedy Intl. Airport (JFK) is one of the busiest airports in Sleepy Hollow. It's around 48 kilometers south of the downtown area. Other options open to you are Liberty Intl. Airport (EWR) (48 kilometers away from central Sleepy Hollow) and LaGuardia Airport (LGA) (32 kilometers away from central Sleepy Hollow).