Sleepy Hollow Vacation Packages 2026 from $996

Sleepy Hollow flight + hotel vacation packages

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

Modern Comfort in the Heart of NYC

Southeast Yonkers

$996

per person

Nov 25 - Nov 30

found 23 hours ago

Roundtrip flight included

Orlando (MCO) to White Plains (HPN)

This apartment doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the laundry service. Laundry facilities and a virtual front desk are also provided.

Luxury NYC Home with Free Parking for 12

Save 100% on your flight

$1,237

per person

Nov 16 - Nov 18

found 4 hours ago

Roundtrip non-stop flight included

San Juan (SJU) to White Plains (HPN)

This villa doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the laundry service. A garden, laundry facilities, and a virtual front desk are also on offer.

Delamar Greenwich Harbor

$1,156

per person

Dec 26 - Dec 30

found 13 hours ago

Roundtrip flight included

Orlando (MCO) to White Plains (HPN)

This boutique hotel features a full-service spa, a marina, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free valet parking. Enjoy the 24-hour gym and perks like free self parking and a free area shuttle.

Luxury NY Home with Free Parking

Save 100% on your flight

$2,330

per person

Dec 27 - Dec 31

found 14 hours ago

Roundtrip non-stop flight included

Fort Myers (RSW) to White Plains (HPN)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. Families will appreciate the onsite laundry facilities and in-room childcare. Dry cleaning and luggage storage are also provided.

3BR Prime Luxury NY - Free Parking

Save 100% on your flight

$2,091

per person

Dec 27 - Dec 31

found 14 hours ago

Roundtrip non-stop flight included

Fort Myers (RSW) to White Plains (HPN)

Top Sleepy Hollow hotels deals

Highbridge Hotel

1263 Edward L Grant Highway Bronx NY

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$141 total

Oct 19 - Oct 20

Total with taxes and fees

This hotel features a gym and a rooftop terrace. Business travelers can take advantage of the free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Breakfast included

Free WiFi

Executive Inn - Fort Lee

2339 Route 4 Fort Lee NJ

Free Cancellation

Reserve now, pay when you stay

$124 nightly

$142 total

Oct 15 - Oct 16

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the express check-out and onsite conference space. There's luggage storage and multilingual staff can provide around-the-clock assistance.

Parking included

Free WiFi

Baymont by Wyndham White Plains - Elmsford

540 Saw Mill River Rd Elmsford NY

$135 nightly

$155 total

Nov 2 - Nov 3

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

Pool

Breakfast included

Radio Hotel

2420 Amsterdam Ave New York NY

Free Cancellation

Reserve now, pay when you stay

$244 nightly

$283 total

Nov 12 - Nov 13

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the express check-out and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Pet friendly

Restaurant

LIV Hotel Bronx - Newly Built

3530 Webster Ave Bronx NY

Free Cancellation

Reserve now, pay when you stay

$161 nightly

$188 total

Oct 15 - Oct 16

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and concierge services are on offer.

Parking included

Free WiFi

Sleepy Hollow Hotel, a Dolce by Wyndham

455 S Broadway Tarrytown NY

$143 nightly

$164 total

Nov 10 - Nov 11

Total with taxes and fees

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Bring the family and enjoy the arcade/game room and kid-friendly dining. Enjoy the sauna and perks like free self parking.

Pool

Spa

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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 with a white and red base, a black top, and a metal railing.

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

Frequently asked questions

How much are vacation packages to Sleepy Hollow?

Travelocity offers flight and hotel vacation packages from an incredible $996. 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 100 mi 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 30 mi south of the downtown area. Other options open to you are Liberty Intl. Airport (EWR) (30 mi away from central Sleepy Hollow) and LaGuardia Airport (LGA) (20 mi away from central Sleepy Hollow).