Sleepy Hollow Vacations from $476

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Sleepy Hollow Vacation

Lock in a custom vacation package to Sleepy Hollow and get ready for your next great escape. Stay in the neighborhood of Northwest Yonkers, which is great for nature and culture, for a real taste of this interesting city. Lyndhurst Mansion, Tarrytown Music Hall and Sleepy Hollow Cemetery are just some of the many sights worth checking out during your trip to Sleepy Hollow. Whatever your travel plans or budget, organizing a tailored Sleepy Hollow vacation is a walk in the park with Expedia.

The Latest Sleepy Hollow vacation packages

Price found within the past 48 hours. Click for updated prices.
Home & Away Hotel-Style

Home & Away Hotel-Style

2 out of 5
West Norwalk
Price was $646, price is now $476 per person
$476
per person
Jan 7 - Jan 10
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to White Plains (HPN)
10/10 Exceptional! (2 reviews)
Newly renovated, nice place

Reviewed on Oct 4, 2026

3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking

2 out of 5
Price was $3,889, price is now $2,871 per person
$2,871
per person
Dec 21 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
6/10 (1 review)
Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected.

Reviewed on Mar 30, 2026

Spacious Retreat with Game Room

Spacious Retreat with Game Room

2.5 out of 5
West Norwalk
Price was $1,087, price is now $816 per person
$816
per person
Jan 7 - Jan 10
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to White Plains (HPN)
10/10 Exceptional! (2 reviews)
We loved the home. I wholeheartedly recommend.

Reviewed on Sep 9, 2026

Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking

3.5 out of 5
Southeast Yonkers
Save 100% on your flight
Price was $3,669, price is now $2,804 per person
$2,804
per person
Dec 13 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to White Plains (HPN)
5/10 (12 reviews)
Though the privous occupants refused to vacate the property in time but the landlord was suupportive went out of their way and provided a refund option and an alternative...we took the alternative which happen to be better than the originally booked property ... Will use this management and property owner in our upcoming short terms rentals.....

Reviewed on Sep 13, 2026

Stamford Marriott

Stamford Marriott

3.5 out of 5
Downtown Stamford
Price was $639, price is now $503 per person
$503
per person
Jan 7 - Jan 10
found 11 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to White Plains (HPN)
8/10 Very Good! (1,000 reviews)

Don't see what you're looking for?
See all available trips from Columbus to Sleepy Hollow
View all trips

Stay near popular Sleepy Hollow attractions

A lighthouse with a white and red base, a black top, and a metal railing.
Photo by Bob Westerfield
Open Photo by Bob Westerfield

Tarrytown Lighthouse

8.4/10 (104 reviews)
This historic 1883 beacon on the Hudson River showcases a unique caisson design and maritime heritage. Climb its five stories to enjoy panoramic river views and glimpse the fascinating life of lighthouse keepers past.
See properties

What to do in Sleepy Hollow

Sleepy Hollow Ghost Tour

Sleepy Hollow Ghost Tour (Self-Guided Audio Driving/Walking Tour)

$10
per adult
Sleepy Hollow Ghost Tour (Self-Guided Audio Driving/Walking Tour)
See all activities in Sleepy Hollow

Sleepy Hollow Hotel Deals

Highbridge Hotel

Highbridge Hotel

2 out of 5
1263 Edward L Grant Highway Bronx NY
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $118 total per night from Nov 3 to Nov 4
$118 total
Nov 3 - Nov 4
Total with taxes and fees
Highbridge Hotel
Radio Hotel

Radio Hotel

4 out of 5
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
$178 nightly
The price is $207 total per night from Nov 22 to Nov 23
$207 total
Nov 22 - Nov 23
Total with taxes and fees
Radio Hotel
Executive Inn - Fort Lee

Executive Inn - Fort Lee

3.5 out of 5
2339 Route 4 Fort Lee NJ
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $142 total per night from Nov 3 to Nov 4
$142 total
Nov 3 - Nov 4
Total with taxes and fees
8/10 Very Good! (1,623 reviews)
"shower had rust around the drain. There was a sheet and no comforter on the bed. One elevator was under construction, so you had to wait longer than usual for the second one to come."

Reviewed on Nov 1, 2026

Executive Inn - Fort Lee
See all 1,846 properties in Sleepy Hollow
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.

Find the Best Sleepy Hollow Vacation Packages

Things to do near Sleepy Hollow

Sleepy Hollow, New York, is perfect for outdoor adventures and family or romantic getaways. Visitors can explore vibrant shopping areas and enjoy local theater. Notable activities include engaging Halloween events, scenic day trips, walking tours, and cemetery tours, all of which highlight the town's rich history and folklore. Embrace the charm of Sleepy Hollow as you discover its unique attractions and experiences.

Shopping

In Sleepy Hollow, you can shop at Rockland Bakery, just 7 miles away, for delightful baked goods. If you're up for a drive, head to Palisades Center, 5 miles away, for a variety of shops and entertainment, or visit Westchester's Ridge Hill, 8 miles away, for more family-friendly options.

Recreation

Tarrytown Music Hall offers an enchanting atmosphere filled with live performances, perfect for an entertaining night out. The Westchester Broadway Theatre provides a charming blend of culture and romance, showcasing captivating productions that delight families. For sports enthusiasts, Yankee Stadium delivers an electrifying experience just 18 miles away.

Adventure

Experience the excitement at Legoland Discovery Center Westchester, 8 miles from Sleepy Hollow, with family-friendly arcade adventures. Challenge yourself at Palisades Climb Adventure, located 5 miles away, featuring thrilling zipline and ropes courses. For high-speed fun, head to Grand Prix New York / Spins Bowl, 12 miles away, for karting excitement.

Nightlife

Experience the vibrant nightlife in Sleepy Hollow with a visit to the Stonewall Inn or Dave & Buster's, both offering great drinks and a lively atmosphere about 24 to 25 miles away. For a unique vibe, check out 51-53 Christopher Street, where entertainment and romance thrive.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Sleepy Hollow

Sleepy Hollow, New York, offers a delightful blend of outdoor activities and cultural experiences for families, couples, and solo travelers. Explore the picturesque Sleepy Hollow Lighthouse and the historic Sleepy Hollow Cemetery, or enjoy the scenic beauty of local parks and preserves. Whether you're seeking adventure or a relaxing getaway, Sleepy Hollow has something for everyone to enjoy amidst its charming surroundings.

  • Westchester County Center: Located 5 miles from Sleepy Hollow, this vibrant arts center hosts a variety of cultural events, including concerts and art exhibitions. Its welcoming atmosphere and diverse programming make it a hub for creativity and community engagement, perfect for art enthusiasts and families alike.
  • Lyndhurst Mansion: Just 2 miles away, this stunning historic mansion offers a glimpse into the opulence of the 19th century. Surrounded by beautiful gardens and scenic views of the Hudson River, visitors can explore its rich architecture and learn about its fascinating history through guided tours.
  • Tarrytown Lighthouse: Situated within Sleepy Hollow, this iconic lighthouse is a picturesque spot for photography and relaxation. With its charming design and historical significance, it's a perfect location to enjoy the river views and immerse yourself in local maritime history.

Best time to go to Sleepy Hollow

The best time to visit Sleepy Hollow is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January30.6°F (-0.8°C)Light RainMostly SunnyLowSlightly Low
February32.2°F (0.1°C)Light RainMostly SunnyLowSlightly Low
March39.6°F (4.2°C)Light RainMostly SunnyAverageSlightly Low
April50.5°F (10.3°C)Light RainMostly SunnyAverageAverage
May60.8°F (16.0°C)Light RainMostly SunnyAverageAverage
June69.4°F (20.8°C)Light RainMostly SunnyAverageAverage
July76.1°F (24.5°C)Light RainMostly SunnyAverageAverage
August74.5°F (23.6°C)Light RainMostly SunnyHighAverage
September67.6°F (19.8°C)Light RainMostly SunnyHighSlightly High
October56.8°F (13.8°C)Light RainMostly SunnyHighSlightly High
November45.0°F (7.2°C)Light RainMostly SunnyAverageAverage
December36.9°F (2.7°C)Light RainMostly SunnyLowSlightly High

Tips to save on your trip to Sleepy Hollow

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically January to March) for more affordable package holidays to Sleepy Hollow.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Sleepy Hollow Essential Information

Language
English
Currency
U.S dollars
Closest Airport
John F. Kennedy Intl. Airport (JFK)
Population
10,200
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Rockefeller Archive Center, Lyndhurst Mansion and Tarrytown Music Hall

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

What are the top things to do in Sleepy Hollow?
A Sleepy Hollow vacation offers a blend of historic sites, scenic outdoor spaces, and family-friendly attractions:

Browse and book things to do in Sleepy Hollow on Expedia.
How can I save money on a Sleepy Hollow vacation package?
When you bundle, you can save up to 30%*. To save money on a Sleepy Hollow package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
Do you need to rent a car in Sleepy Hollow, or is public transport enough?
A rental car is generally recommended for a Sleepy Hollow vacation package, offering the most flexibility to explore the region's outdoor and historic attractions. While the central village area is walkable, and local taxis are available, many of the scenic and family-friendly sites are spread out. For instance, a car makes it easy to visit Lyndhurst Mansion, about 1 mile away, or venture further to Bear Mountain State Park, about 16 miles from central Sleepy Hollow. If your Sleepy Hollow vacation packages with flights include a stay in a local hotel or motel, having your own vehicle becomes particularly useful for day trips and reaching various points of interest. Travelers often arrive via New York, NY (JFK-John F. Kennedy Intl.), Newark Liberty Intl. Airport (EWR), or White Plains, NY (HPN-Westchester County).
Can I change or cancel my Sleepy Hollow vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Sleepy Hollow vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Sleepy Hollow vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Sleepy Hollow vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Sleepy Hollow?
To find last-minute vacation packages to Sleepy Hollow, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Sleepy Hollow vacation packages?
Free cancellation on a Sleepy Hollow vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Sleepy Hollow vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Sleepy Hollow getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Sleepy Hollow vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.