Sleepy Hollow Holidays

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Things to do near Sleepy Hollow

Sleepy Hollow offers a delightful blend of outdoor activities ideal for families and couples alike. Visitors can enjoy a vibrant shopping area and theatre, alongside exciting attractions such as live music events, fun tours, and time sightseeing. Don't miss the lively block party, which showcases the community's spirit and charm. This charming destination promises a memorable experience filled with entertainment and exploration.

Shopping

For a delightful shopping experience in Sleepy Hollow, explore local boutiques and shops. If you're up for a drive, Westfield Garden State Plaza and The Outlets at Bergen Town Center, both located 25.7km away, offer a variety of shops and entertainment. Riverside Square Mall is also 24.1km away.

Recreation

Experience the serene greens at Sprain Lake Golf Course, just 11.3km away, perfect for a relaxing round of golf amidst nature. Enjoy captivating performances at Tarrytown Music Hall, only 966m away, for an enriching cultural encounter. For sports enthusiasts, Yankee Stadium, 29.0km away, offers thrilling games.

Adventure

Experience the thrill of Legoland Discovery Center Westchester, an arcade adventure zone 12.9km from Sleepy Hollow, perfect for family fun. Explore the Orange Trailhead for outdoor adventure 3.2km away, or hike the scenic Yellow Trailhead, located 4.8km from Sleepy Hollow, for breathtaking views.

Nightlife

In Sleepy Hollow, nightlife offers a charming atmosphere with venues like Dave & Buster's, Stonewall Inn, and 51-53 Christopher Street, all providing a blend of romance and entertainment vibes. Explore these local pubs for a delightful evening filled with drinks and lively conversations.

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

Find the best attractions near Sleepy Hollow

Sleepy Hollow, New York, is ideal for outdoor, family, and romantic getaways. Explore popular attractions such as urban parks, modern colleges, and nature reserves that cater to diverse interests. Essential activities include visiting the iconic Sleepy Hollow Cemetery and discovering local attractions, ensuring a well-rounded cultural and family experience in this charming village.

  • Fordham University: Experience the vibrant atmosphere of Fordham University, a modern institution located 25.7km from Sleepy Hollow. Stroll through its picturesque campus, where urban energy meets academic excellence, providing an engaging environment for exploration.
  • George Washington Bridge: At 27.4km from Sleepy Hollow, the historic George Washington Bridge offers stunning views and a glimpse into its cultural significance. Walk across this engineering marvel and soak in the rich history that surrounds this iconic landmark.
  • Van Cortlandt Park: Just 20.9km away, Van Cortlandt Park is a delightful urban retreat perfect for families. Enjoy outdoor activities amidst scenic landscapes, making it an ideal spot for picnics, leisurely walks, and engaging in nature.

Best time to go to Sleepy Hollow

The best time to visit Sleepy Hollow can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Sleepy Hollow falls in July, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Sleepy Hollow falls in January, 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 to Sleepy Hollow during the low season (January to March) for more affordable options.
  • 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.

Top hotels in Sleepy Hollow

Highbridge Hotel

Highbridge Hotel

2 out of 5
1263 Edward L Grant Highway Bronx NY
Fully refundableReserve now, pay when you stay
The price is S$110 per night from 16 Nov to 17 Nov
S$110
16 Nov - 17 Nov
includes taxes & fees
9.2/10 Wonderful! (4,333 reviews)
"Thank you to all the staff who made sure from head to foot ,everything was ok from front desk service, to even to the cooks the whole entire team. Down to the guys how do the ground work Thanks."

Reviewed on 8 Nov, 2026

Highbridge Hotel
Radio Hotel

Radio Hotel

4 out of 5
2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
The price is S$263 per night from 23 Nov to 24 Nov
S$263
23 Nov - 24 Nov
includes taxes & fees
8.4/10 Very good! (2,343 reviews)
"Love the restaurant!"

Reviewed on 8 Nov, 2026

Radio Hotel
LIV Hotel Bronx - Newly Built

LIV Hotel Bronx - Newly Built

3 out of 5
3530 Webster Ave Bronx NY
Fully refundableReserve now, pay when you stay
The price is S$166 per night from 11 Nov to 12 Nov
S$166
11 Nov - 12 Nov
includes taxes & fees
7.2/10 Good! (1,249 reviews)
"Sheet had a hole, little stains on pillow"

Reviewed on 8 Nov, 2026

LIV Hotel Bronx - Newly Built
See all 1,757 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.

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

Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

S$901
per traveller
Introductory Helicopter Flight Lesson from Westchester
See all activities in Sleepy Hollow

Frequently asked questions

How much does a Sleepy Hollow holiday package cost?
You'll find cheap prices on Expedia for your Sleepy Hollow getaway. However, factors like the hotel choice, length of stay and season will influence how much your holiday to Sleepy Hollow costs.
What are the cheapest months to go to Sleepy Hollow?
If you're looking to book a cheap Sleepy Hollow holiday package, consider visiting in January, February and March. You're likely to find lower rates on flights and hotels during these months — perfect for budget-conscious travellers.
How many days is enough for Sleepy Hollow?
With a well-planned schedule, you can easily hit the main Sleepy Hollow sights in a few days. But if you'd like to discover hidden spots or take day trips, think about booking your Sleepy Hollow holiday for longer.
Is it worth booking a holiday package to Sleepy Hollow?
Sleepy Hollow has everything you need for an awesome trip — nature, culture and history are just the start. Whether you want to check out sights like Tarrytown Lighthouse and Old Dutch Church of Sleepy Hollow, or venture off the beaten track, you'll find plenty to see and do on your Sleepy Hollow holiday.
How to find the best Sleepy Hollow package deals?
Landing a cheap Sleepy Hollow package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, apply a few filters and browse what's available. You can customise your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most economical Sleepy Hollow package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Sleepy Hollow holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging flights and hotels separately. Better still, you can tailor your Sleepy Hollow getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Sleepy Hollow?
If you've got your Sleepy Hollow travel dates finalized, book as early as you can to score some fantastic deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Sleepy Hollow?

  1. Pick your dates: What you'd like to do in Sleepy Hollow and your preferred season can help you decide when to go.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and food to flights and experiences. Your hotel will likely be the biggest expense during your trip to Sleepy Hollow.
  3. Decide how long to go away for: Now that you know more about Sleepy Hollow, you can figure out the right length of your break. Put together a rough plan and give yourself enough time for all the things you want to do.
  4. Combine your airfare and accommodation: After you've settled on your dates and duration, book the perfect Sleepy Hollow holiday package for you.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.