A wooden structure with a bridge over a body of water, surrounded by trees.

Sleepy Hollow Vacation Packages

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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.

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

    Photo by Bob Westerfield

    Tarrytown Lighthouse

    Rating: 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.

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    A white house with a wooden deck and a wooden bridge over a river.

    Philipsburg Manor

    Rating: 8.2/10 (40 reviews)

    You can find out about the history of Sleepy Hollow with a trip to Philipsburg Manor. Wander the riverfront in this quaint area.

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    A historic stone building with a tower and a black iron fence.

    Old Dutch Church of Sleepy Hollow

    Rating: 8.6/10 (74 reviews)

    You can learn about the history of Sleepy Hollow with a trip to Old Dutch Church of Sleepy Hollow. Wander the riverfront in this family-friendly area.

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    What to do in Sleepy Hollow

    Helicopter landing in a field in New York

    Introductory Helicopter Flight Lesson from Westchester

    CA $1,046

    per traveller

    0% of travellers recommend

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    Sleepy Hollow Hotel Deals

    Sleepy Hollow Hotel, a Dolce by Wyndham

    A spacious room with a stone fireplace, white sofas, and a large window offering a view of the outdoors.
    • Address: 455 S Broadway, Tarrytown, NY, 10591, US
    • Location: 2.8 km from Sleepy Hollow
    • Star rating: 3.5/5
    • Guest rating: 7/10 (Good, 1007 reviews)
    • Price: CA $189, CA $217 total, includes taxes & fees, Dec 8 - Dec 9

    SpringHill Suites by Marriott Tarrytown Westchester County

    A hotel with a modern facade, a prominent signage for SpringHill Suites Marriott, and a covered entrance area with seating.
    • Address: 480 White Plains Rd, Tarrytown, NY, 10591, US
    • Location: 2.8 km from Sleepy Hollow
    • Star rating: 3/5
    • Guest rating: 8.8/10 (Excellent, 1000 reviews)
    • Price: CA $222, CA $254 total, includes taxes & fees, Dec 14 - Dec 15
    • Review: Nice clean hotel. Staff was friendly. Breakfast was quite good.

    Sheraton Tarrytown Hotel

    A spacious lobby with a reception desk, sofas, and a coffee table. There are multiple seating areas and a large window providing natural light.
    • Address: 600 White Plains Rd, Tarrytown, NY, 10591, US
    • Location: 3.2 km from Sleepy Hollow
    • Star rating: 3.5/5
    • Guest rating: 8.4/10 (Very good, 1003 reviews)
    • Price: CA $193, CA $221 total, includes taxes & fees, Nov 22 - Nov 23
    • Review: The room was clean quiet and comfortable with tasteful decor. Nice area. Felt safe

    Tarrytown House Estate

    A historic stone building with a turret, arched entrance, and a covered patio area.
    • Address: 49 E Sunnyside Lane, Tarrytown, NY, 10591, US
    • Location: 4 km from Sleepy Hollow
    • Star rating: 3.5/5
    • Guest rating: 8.2/10 (Very good, 1435 reviews)
    • Price: CA $267, CA $342 total, includes taxes & fees, Nov 22 - Nov 23

    Holiday Inn Express & Suites Hawthorne Elmsford North by IHG

    A modern reception area with a wooden reception desk, a blue accent wall, and a large glass door leading to an outdoor seating area.
    • Address: 20 Saw Mill River Rd., Hawthorne, NY, 10532, US
    • Location: 3.6 km from Sleepy Hollow
    • Star rating: 2.5/5
    • Guest rating: 9/10 (Wonderful, 1003 reviews)
    • Price: CA $158, CA $181 total, includes taxes & fees, Dec 14 - Dec 15
    • Review: Clean facility, friendly staff

    Hotel Nyack, a JdV by Hyatt Hotel

    A modern bar area with a bar counter, multiple stools, and a seating area with a sofa and chairs.
    • Address: 400 High Avenue, Nyack, NY, 10960, US
    • Location: 6.1 km from Sleepy Hollow
    • Star rating: 4/5
    • Guest rating: 8.6/10 (Excellent, 1333 reviews)
    • Price: CA $166, CA $229 total, includes taxes & fees, Nov 29 - Nov 30

    Baymont by Wyndham White Plains - Elmsford

    A modern hotel lobby with a kitchen area, seating arrangements, and large windows offering a view of the outdoors.
    • Address: 540 Saw Mill River Rd, Elmsford, NY, 10523, US
    • Location: 3.9 km from Sleepy Hollow
    • Star rating: 2.5/5
    • Guest rating: 8.2/10 (Very good, 1902 reviews)
    • Price: CA $192, CA $219 total, includes taxes & fees, Dec 13 - Dec 14
    • Review: "3/5 Stars: Clean Room, But the "Heated" Pool Was a Major Letdown We chose Baymont by Wyndham Elmsford / White Plains specifically because we wanted to unwind in their advertised indoor heated pool, and we were willing to pay a little extra for that perk. Unfortunately, that turned out to be our biggest disappointment of the stay. The Pool (Biggest Letdown): From the parking area, you can see right into the pool area, and my husband and I kept wondering why it was always completely empty. Once...

    Days Inn by Wyndham Elmsford / White Plains

    A breakfast area with multiple tables and chairs, a kitchen area with appliances, and a sign for Daybreak Breakfast.
    • Address: 25 Valley Ave, Elmsford, NY, 10523, US
    • Location: 4.6 km from Sleepy Hollow
    • Star rating: 2/5
    • Guest rating: 7.4/10 (Good, 1043 reviews)
    • Price: CA $156, CA $178 total, includes taxes & fees, Nov 22 - Nov 23
    • Review: The room was clean, and the parking was ok. Very close to attractions.

    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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    Frequently Asked Questions

    How much does a Sleepy Hollow vacation package cost?

    You can snap up a vacation package to this popular destination from CA $997 on Expedia. However, how much your vacation to Sleepy Hollow costs will depend on the season, length of stay and hotel choice.

    What are the cheapest months to go to Sleepy Hollow?

    January, February and March are the best times to search for cheap Sleepy Hollow vacation packages. Travelling in less busy periods means you can generally find lower prices on flights and accommodations.

    How many days is enough for Sleepy Hollow?

    With a well-planned schedule, you can easily tick off 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 trips, consider booking your Sleepy Hollow vacation for longer.

    Is it worth booking a vacation package to Sleepy Hollow?

    Popular for its nature, culture and history, a Sleepy Hollow vacation is a hit with all kinds of travellers. Be sure to visit leading sights like Tarrytown Lighthouse and Old Dutch Church of Sleepy Hollow, and consider renting a set of wheels for day trips to experience even more.

    How to find the best Sleepy Hollow package deals?

    Begin your search for a Sleepy Hollow package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Sleepy Hollow package deal straight away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Sleepy Hollow adventure off to a flying start.

    Is it cheaper to book a Sleepy Hollow vacation as a package?

    Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component individually. And you'll still have the flexibility to create a customized Sleepy Hollow vacation by choosing your favourite airline, accommodation type and car class.

    When to book a vacation package to Sleepy Hollow?

    Score incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Sleepy Hollow trip.

    How to plan a trip to Sleepy Hollow?

    1. Pick your travel dates: The things you plan to do in Sleepy Hollow and your favourite season can help you decide when to go.
    2. Set your budget: Consider costs such as flights, transportation and food when calculating how much to set aside for your trip to Sleepy Hollow. Then, pick a hotel that suits your budget, whether that's a wallet-friendly option or a high-end retreat.
    3. Work out your trip length: Think about how much time you'd like to spend exploring Sleepy Hollow. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
    4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to pick a Sleepy Hollow vacation package that brings all your bookings together.

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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.