How much does a Sleepy Hollow vacation package cost?

You'll find cheap prices from $339 on Expedia for your Sleepy Hollow getaway. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Sleepy Hollow costs.

What are the cheapest months to go to Sleepy Hollow?

If you're hoping to book a cheap Sleepy Hollow vacation package, consider planning a trip in January, February and October. You'll usually find lower rates on accommodations and flights during these months — perfect for a budget-friendly getaway.

How many days is enough for Sleepy Hollow?

With a well-organized travel plan, you can easily hit the main Sleepy Hollow sights in a handful of days. But if you'd like to venture off the beaten track or go on day tours, think about booking your Sleepy Hollow vacation for longer.

Is it worth booking a vacation package to Sleepy Hollow?

Sleepy Hollow has everything you need for an awesome break — nature, culture and history are just the start. Whether you'd like to check out sights like Tarrytown Lighthouse and Old Dutch Church of Sleepy Hollow , or take the path less traveled, you'll find plenty to see and do on your Sleepy Hollow vacation.

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 customize 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 vacation as a package?

An Expedia vacation 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 vacation 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?

Choose when to travel: Check your calendar and get your bags packed. Your favorite season and the available activities will also help you decide when to escape to Sleepy Hollow. Work out your budget: Make sure you have enough money to pay for everything from dining out and transportation to flights and activities. Your accommodations will probably be the largest expense during your trip to Sleepy Hollow. Explore Sleepy Hollow with our trip planning tool : Gain insights into the top attractions and best hotels for your trip to Sleepy Hollow. You can also save your favorite places, collaborate with your group and organize your plans in one place. Decide how long to go for: Now that you know more about Sleepy Hollow, you can figure out the perfect length of your vacation. Pull together a rough itinerary and give yourself enough time for all the things you want to do. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a personalized Sleepy Hollow vacation package. Book any activities or excursions: Here's the fun part — locking in everything you want to do and see. Explore some of the exciting things to do in Sleepy Hollow and reserve your tickets in advance to save time (and maybe some dollars too!).

Does Expedia offer Book Now, Pay Later Sleepy Hollow vacation packages?

Jet off on your perfect escape to Sleepy Hollow with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait for payday — we've teamed up with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans mean you can spread the cost across 3, 6 or 12 months. With no late payment fees or extra charges, you can easily stick to your budget and snap up bargains before they disappear.

Sleepy Hollow Vacation Packages 2025/2026 from $367

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.

EVEN Hotel Norwalk by IHG

Save 100% on your flight

per person

Sep 19 - Sep 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to White Plains (HPN)

8.4/10 Very Good! (1,005 reviews)

Hotel is fine. Areas a little wonky

Reviewed on Aug 9, 2025

The Armon Stamford Hotel & Conference

Ridgeway-Bullshead

Save 100% on your flight

per person

Oct 12 - Oct 15

found 20 hours ago

Roundtrip flight included

Dallas (DFW) to White Plains (HPN)

7.8/10 Good! (503 reviews)

The hotel was very nice, with clean huge rooms. The hotel design is a hollow cube, so all the rooms look out over an indoor area. This area would be nice for a conference or maybe a wedding. The hotel has all the expected amenities (gym, etc). It is a reasonably priced and well situated hotel. I would go there again.

Reviewed on Aug 2, 2025

The Stamford Hotel

Downtown Stamford

Save 100% on your flight

per person

Oct 28 - Nov 4

found 1 day ago

Roundtrip non-stop flight included

Dallas (DAL) to White Plains (HPN)

7.8/10 Good! (1,088 reviews)

Parking horrible, its $25 No complementary breakfast Oudated hotel

Reviewed on Aug 10, 2025

Global Luxury Suites White Plains

per person

Oct 29 - Nov 1

found 19 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to White Plains (HPN)

6.8/10 (31 reviews)

Nice view from the apartment and great for business trip.

Reviewed on Dec 16, 2024

Hotel NoMa, Trademark Collection by Wyndham

Save 100% on your flight

per person

Oct 30 - Nov 2

found 19 hours ago

Roundtrip flight included

Charlotte (CLT) to White Plains (HPN)

8/10 Very Good! (1,004 reviews)

Marie and her staff were super helpful! Kevin(server) was awesome! And good was delicious! Convient to train. Definitely would stay there again. Thank you.

Reviewed on Aug 8, 2025

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Sleepy Hollow Hotel Deals

Hampton Inn White Plains/Tarrytown

200 West Main Street, Elmsford, NY

Fully refundableReserve now, pay when you stay

$127 nightly

$145 total

Sep 1 - Sep 2

Total includes taxes and fees

7.8/10 Good! (1,095 reviews)

"Great place to stay. Breakfast was good. Easy access to Highways."

Reviewed on Aug 5, 2025

Baymont by Wyndham White Plains - Elmsford

540 Saw Mill River Rd, Elmsford, NY

Fully refundableReserve now, pay when you stay

$144 nightly

$164 total

Aug 17 - Aug 18

Total includes taxes and fees

8.2/10 Very Good! (1,389 reviews)

"Super comfy bed breakfast was great"

Reviewed on Aug 7, 2025

Executive Inn - Fort Lee

2339 Route 4, Fort Lee, NJ

Fully refundableReserve now, pay when you stay

$104 nightly

$119 total

Aug 11 - Aug 12

Total includes taxes and fees

7.6/10 Good! (349 reviews)

"It was perfect and affordable!"

Reviewed on Aug 9, 2025

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.

Things to do near Sleepy Hollow

Sleepy Hollow offers a picturesque setting perfect for outdoor and romantic getaways. Visitors can enjoy a variety of activities including shopping, skiing, and walking tours. The area is particularly vibrant during Halloween, featuring special events and cemetery tours that delve into the town's rich history. Whether you're looking for a day trip or unique experiences, Sleepy Hollow has something to captivate everyone.

Shopping

For shopping in Sleepy Hollow, visit Rockland Bakery, a great spot for delicious treats just 7 miles away. If you're up for a drive, check out Palisades Center, 5 miles away, or Westchester's Ridge Hill, 8 miles away, both offering a variety of shops and family-friendly vibes.

Recreation

Experience the vibrant atmosphere at Tarrytown Music Hall, where live performances will uplift your spirits. For a blend of culture and romance, enjoy a show at Westchester Broadway Theatre, just 2 miles away, offering family-friendly entertainment in a charming setting.

Adventure

Experience excitement at Legoland Discovery Center Westchester, 8 miles from Sleepy Hollow, with thrilling arcade games for the whole family. For outdoor fun, tackle the zipline and ropes course at Palisades Climb Adventure, located 5 miles away. Don't miss the karting at Grand Prix New York, 12 miles from town.

Nightlife

Sleepy Hollow's nightlife offers a charming mix of entertainment and romance. Enjoy drinks at Stonewall Inn, Dave & Buster's, or 51-53 Christopher Street, each providing a vibrant atmosphere perfect for unwinding and socializing after a day of exploring this historic area.

*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 charming blend of outdoor adventures and cultural experiences, perfect for romantic getaways or family trips. Explore the scenic beauty of local parks, visit the historic Sleepy Hollow Cemetery, and admire the iconic lighthouse. With its captivating landscapes and rich history, Sleepy Hollow is an ideal destination for those seeking to immerse themselves in nature and culture.

Westchester County Center: Located 5 miles from Sleepy Hollow, this vibrant arts center offers a mix of performances and events, highlighting local culture and talent. It’s a great venue to experience the artistic heartbeat of Westchester County.
Lyndhurst Mansion: Just 2 miles away, this stunning historic estate features beautiful architecture and lush gardens. Visitors can explore its rich history and enjoy guided tours that delve into the lives of its former residents.
Tarrytown Lighthouse: Situated within Sleepy Hollow, this charming lighthouse not only provides picturesque views of the Hudson River but also tells the story of maritime history in the region, making it a lovely spot for photography and exploration.

Best time to go to Sleepy Hollow

The best time to visit Sleepy Hollow is dependant 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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	30.6°F (-0.8°C)	Light Rain	Mostly Sunny	Low	Slightly Low
February	32.2°F (0.1°C)	Light Rain	Mostly Sunny	Low	Slightly Low
March	39.6°F (4.2°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	50.5°F (10.3°C)	Light Rain	Mostly Sunny	Average	Average
May	60.8°F (16.0°C)	Light Rain	Mostly Sunny	Average	Average
June	69.4°F (20.8°C)	Light Rain	Mostly Sunny	Average	Average
July	76.1°F (24.5°C)	Light Rain	Mostly Sunny	Average	Average
August	74.5°F (23.6°C)	Light Rain	Mostly Sunny	High	Average
September	67.6°F (19.8°C)	Light Rain	Mostly Sunny	High	Slightly High
October	56.8°F (13.8°C)	Light Rain	Mostly Sunny	High	Slightly High
November	45.0°F (7.2°C)	Light Rain	Mostly Sunny	Average	Average
December	36.9°F (2.7°C)	Light Rain	Mostly Sunny	Low	Slightly 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.