Sleepy Hollow Vacations

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to ¥109,000 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
Price found within the past 48 hours. Click for updated prices.
  • Jul 3 - Jul 6

    The Delaney Hotel + Flight

    South Orange
    3 nights
    3.5 star property
    9.6/10 - Exceptional (1,106 reviews)
    "From the moment we checked in, everything about this hotel stay was amazing. The hotel was spotless, beautifully decorated, and so relaxing. The rooms were clean, comfortable, and smelled fresh the entire stay. The staff was welcoming and made sure we had everything we needed. Definitely one of the most beautiful and peaceful hotel experiences we’ve had. Can’t wait to come back!"
    Reviewed May 19, 2026
    Roundtrip Detroit (DTW) - Orlando (MCO)
    DTW - MCO1 stop MCO - DTW1 stop
    ¥110,333
    ¥76,379
    per traveler
    found 1 day ago
    The Delaney Hotel
  • Jul 3 - Jul 6

    Florida Hotel & Conference Center in the Florida Mall + Flight

    Orlando
    3 nights
    3.5 star property
    9.2/10 - Wonderful (1,353 reviews)
    "Loved everything about this hotel"
    Reviewed May 19, 2026
    Roundtrip Detroit (DTW) - Orlando (MCO)
    DTW - MCO1 stop MCO - DTW1 stop
    Save 100% on your flight
    ¥125,557
    ¥81,744
    per traveler
    found 1 day ago
    Florida Hotel & Conference Center in the Florida Mall
  • Aug 13 - Aug 17

    Mission to Mars + Flight

    Loughman
    4 nights
    4.0 star property
    Roundtrip Tokyo (NRT) - Orlando (MCO)
    NRT - MCO1 stop MCO - NRT1 stop
    Save 100% on your flight
    ¥1,489,257
    ¥1,107,127
    per traveler
    found 0 hours ago
    Mission to Mars
  • Jul 13 - Jul 19

    Seasons Florida Resort + Flight

    Kissimmee
    6 nights
    2.0 star property
    9.0/10 - Wonderful (3,558 reviews)
    "The staff was great and the room was clean. The price was reasonable and close to other things."
    Reviewed May 18, 2026
    Roundtrip Tokyo (HND) - Orlando (MCO)
    HND - MCO1 stop MCO - HND1 stop
    ¥263,807
    ¥209,964
    per traveler
    found 15 hours ago
    Seasons Florida Resort
  • Jul 13 - Jul 19

    Palazzo Lakeside Hotel + Flight

    Kissimmee
    6 nights
    3.0 star property
    8.2/10 - Very Good (5,137 reviews)
    "For the price I was pleasantly surprised and enjoyed the night my kids and I spent. It’s an odd looking building, kinda looks like a pyramid or prison lol. The decor inside was clean, very modern and fancy. My kids thought the kids club room with the Xbox’s was awesome and so did I. The outside area was nice with the lake, gazebos, play area, and pool. There is some sort of construction going on but the staff said they are making an outdoor movie area by the pool which I thought was cool...."
    Reviewed May 19, 2026
    Roundtrip Tokyo (HND) - Orlando (MCO)
    HND - MCO1 stop MCO - HND1 stop
    ¥261,493
    ¥213,426
    per traveler
    found 12 hours ago
    Palazzo Lakeside Hotel

Where to stay in Sleepy Hollow

Find the best Sleepy Hollow areas and neighborhoods for the activities you enjoy most. Learn more about Sleepy Hollow

Sleepy Hollow Hotel Deals

Hilton Daytona Beach Oceanfront Resort

Hilton Daytona Beach Oceanfront Resort

4 out of 5
100 N Atlantic Ave Daytona Beach FL
Fully refundableReserve now, pay when you stay
The price is ¥16,090 per night from May 31 to Jun 1
¥16,090
¥22,576 total
May 31 - Jun 1
includes taxes & fees
7.4/10 Good! (4,863 reviews)
"good breakfast buffet but pricey, hotel is outdated and needs maintenance"

Reviewed on May 20, 2026

Hilton Daytona Beach Oceanfront Resort
Daytona Grande Oceanfront Resort

Daytona Grande Oceanfront Resort

4 out of 5
422 N Atlantic Ave Daytona Beach FL
Fully refundableReserve now, pay when you stay
The price is ¥23,522 per night from Jun 3 to Jun 4
¥23,522
¥32,726 total
Jun 3 - Jun 4
includes taxes & fees
9.2/10 Wonderful! (4,657 reviews)
"Yrs"

Reviewed on May 20, 2026

Daytona Grande Oceanfront Resort
Nautilus Inn

Nautilus Inn

2.5 out of 5
1515 S Atlantic Ave Daytona Beach FL
Fully refundableReserve now, pay when you stay
The price is ¥14,197 per night from May 25 to May 26
¥14,197
¥15,971 total
May 25 - May 26
includes taxes & fees
9.2/10 Wonderful! (3,156 reviews)
"Nice view"

Reviewed on May 20, 2026

Nautilus Inn
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.

Frequently asked questions

How much does a Sleepy Hollow vacation package cost?
From just , you can customize your Sleepy Hollow package the way you want. Simply combine hotels, flights and rental cars and we'll reward you with discounts.
How do I get a cheap travel package to Sleepy Hollow?
Browse and book everything in one place with our Sleepy Hollow vacation packages. You'll find bargains on flights, hotels, tours and more that'll keep your pocketbook happy and your adventurous spirit full. And, with more than 550 partner airlines and 1,000,000 hotel options around the globe to pick from, you have countless opportunities to mix and match all you want.
Where should I stay in Sleepy Hollow?
With popular attractions such as Go-Kart City and Halifax Health Medical Center of Port Orange in this neighborhood, look for a hotel positioned near them. Port Orange Sport Complex is another Sleepy Hollow hot spot that people flock to.
What are the top hotels in Sleepy Hollow?
If it's comfort and convenience you'd like, you can't go wrong with Cute Cottage With Pool. Close To The Beach - No Water Or Wind Damage From Ian. Spend your evenings unwinding here and your days discovering Sleepy Hollow's finest sights.
How far in advance should I book my Sleepy Hollow vacation?
It's hard to pick the ideal time for airfares, but we generally suggest the earlier, the better. Most international journeys on Expedia become available to compare up to a year in advance. If you're booking at the last minute, don't fret. Low prices appear from time to time just weeks before departure dates.
What does an Expedia Sleepy Hollow travel package include?
Flights, rental cars and hotels, or any combination of them — it's up to you! Whether you're exploring Sleepy Hollow on a family road trip or traveling solo, there's a bundle to match your budget and style. Once you've made your booking, why not add on a few tours or activities?
What should I know before booking a Sleepy Hollow travel package?
You can save a tidy sum by combining your hotels, airfares and rental cars. Once you've created your package, add on fun stuff like activities or sightseeing tours. Your next unforgettable vacation is only a couple of clicks away.
Can I choose my airline with a Sleepy Hollow Expedia vacation package?
Definitely. Expedia has more than 550 airline partners to select from across the world. With so much choice, finding the perfect carrier to whisk you away to Sleepy Hollow won't be difficult.
If I'm not able to travel, can I cancel my Sleepy Hollow vacation package?
If your travel plans in Sleepy Hollow have changed, it's good to know that it is possible to amend or cancel your booking. If you made your booking in the last 24 hours, you may be eligible to receive a refund. If your booking is older than that, your airline, hotel or car rental company may charge a fee. For more details, check our Customer Service Portal.

Things to do

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