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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.
Modern Luxury Home w GameRoom & Parking
3BR Prime Luxury near NYC w Arcade Room
Luxury NY Home with Free Parking
Luxury 3BR Home Game Room Free Parking
Luxury NYC Home Game Room Free Parking

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

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
$80 nightly
The price is $95 total per night from May 25 to May 26
$95 total
25 May - 26 May
Total with taxes and fees
9.2/10 Wonderful! (4,270 reviews)
Easy walk to the OMNY station and conveniently located just down the road from Yankee Stadium

Reviewed on 16 May, 2026

Highbridge 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
$133 nightly
The price is $153 total per night from May 28 to May 29
$153 total
28 May - 29 May
Total with taxes and fees
8/10 Very Good! (987 reviews)
Good location has big parking lot

Reviewed on 15 May, 2026

Executive Inn - Fort Lee
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303 Orangeburg NY
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $88 total per night from May 28 to May 29
$88 total
28 May - 29 May
Total with taxes and fees
6/10 (2,197 reviews)
Staff was good but not worth it’s too old no proper amenities or food available, hair dryer not working, it smells like burning

Reviewed on 16 May, 2026

Armoni Inn & Suites
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.

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