Sleepy Hollow Holidays

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  • Better together

    Save up to S$1,300 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.
  • Reception
    Jul 3 - Jul 6

    Seasons Florida Resort + Flight

    Kissimmee
    3 nights
    2.0 star property
    9.0/10 - Wonderful (3,583 reviews)
    "First time staying here but was impressed by how quiet it was and the cleanliness of the room. Was only there one night but we would definitely stay there again."
    Reviewed May 27, 2026
    Return • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Direct MCO - BOS • Direct
    S$763
    S$519
    per traveller
    found 18 hours ago
    Seasons Florida Resort
  • Terrace/patio
    Jul 3 - Jul 6

    The Delaney Hotel + Flight

    South Orange
    3 nights
    3.5 star property
    9.6/10 - Exceptional (1,110 reviews)
    "My stay at The Delaney was amazing. Everyone was so kind. I will also like to mention how pleasurable it is to hear a staff member mention to another guest how much they enjoyed working there. I will definitely book again."
    Reviewed May 26, 2026
    Return • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Direct MCO - BOS • Direct
    S$953
    S$687
    per traveller
    found 18 hours ago
    The Delaney Hotel
  • View from room
    Jul 3 - Jul 6

    Waldorf Astoria Orlando - An Official Walt Disney World® Hotel + Flight

    Orlando
    3 nights
    5.0 star property
    9.4/10 - Exceptional (523 reviews)
    "Staff was extremely helpful. New hotel. Nice to have cafe etc. -best meal of trip was teriyaki salmon at bar!!! Great for a Disney vacay( free transfer to parks) with LESS little kids. Eventually may be nice to have sundries shop, another restaurant but great hotel. Also suggest a few suites with washer dryer would be helpful."
    Reviewed May 25, 2026
    Return • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Direct MCO - BOS • Direct
    S$1,299
    S$1,011
    per traveller
    found 18 hours ago
    Waldorf Astoria Orlando - An Official Walt Disney World® Hotel
  • 2 outdoor pools, pool loungers
    Jul 3 - Jul 6

    Hilton Orlando Lake Buena Vista - Disney Springs® Area + Flight

    Lake Buena Vista
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,623 reviews)
    "Everything was exceptional."
    Reviewed May 27, 2026
    Return • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Direct MCO - BOS • Direct
    S$852
    S$682
    per traveller
    found 18 hours ago
    Hilton Orlando Lake Buena Vista - Disney Springs® Area
  • Aerial view
    Jul 3 - Jul 6

    The Grove Resort & Water Park Orlando + Flight

    Winter Garden
    3 nights
    4.0 star property
    8.0/10 - Very good (10,013 reviews)
    "Staff was extremely rude while checking in, was NOT informed there was an additional $300 hold on a major credit card, women at front desk refused to use a debit card while talking badly in Spanish not realizing I speak fluent Spanish. Extremely unprofessional. We arrived Saturday- house keeping didn’t clean/replace towels, until Monday night when we left Tuesday morning. My watch and money was missing from the room which we locked one of the bedroom doors prior to heading down to the..."
    Reviewed May 27, 2026
    Return • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Direct MCO - BOS • Direct
    S$1,200
    S$983
    per traveller
    found 18 hours ago
    The Grove Resort & Water Park Orlando

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
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Fly In Spruce Creek

While Fly In Spruce Creek isn't home to many top sights, Spruce Creek Country Club and Airport Road Park are some notable places to visit nearby.

Find hotels in Fly In Spruce Creek

Top hotels in Sleepy Hollow

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 S$169 per night from 10 Jun to 11 Jun
S$169
10 Jun - 11 Jun
includes taxes & fees
7.4/10 Good! (4,892 reviews)
"The room was horrible, the beds were so uncomfortable and hard for it be a Hilton and you could hear the roaring AC from our room 24/7 and the carpet was damp feeling everywhere in the whole room."

Reviewed on 26 May, 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 S$274 per night from 10 Jun to 11 Jun
S$274
10 Jun - 11 Jun
includes taxes & fees
9.2/10 Wonderful! (4,675 reviews)
"Staff was great, rooms were clean"

Reviewed on 26 May, 2026

Daytona Grande Oceanfront Resort
Nautilus Inn

Nautilus Inn

2.5 out of 5
1515 S Atlantic Ave Daytona Beach FL
The price is S$180 per night from 10 Jun to 11 Jun
S$180
10 Jun - 11 Jun
includes taxes & fees
9.2/10 Wonderful! (3,166 reviews)
"Efficient, convenient hotel"

Reviewed on 27 May, 2026

Nautilus Inn
See all 8,174 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.

Frequently asked questions

How much does a Sleepy Hollow holiday 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 holiday 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 Centre of Port Orange in this neighbourhood, 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 holiday?
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 travelling 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 holiday is only a couple of clicks away.
Can I choose my airline with a Sleepy Hollow Expedia holiday 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 holiday 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

Daytona Beach: Luau with Polynesian Dinner and Live Show

Daytona Beach: Luau with Polynesian Dinner and Live Show

S$67
per adult
92% of travellers recommend
Daytona Beach: Luau with Polynesian Dinner and Live Show
Zipline Adventure through Tuscawilla Park

Zipline Adventure through Tuscawilla Park

S$75
per adult
100% of travellers recommend
Zipline Adventure through Tuscawilla Park
Small-Group Sailing Tour in Daytona Beach

Catamaran Sailing Dolphin/Manatee Watch in Daytona Beach

S$88
per adult
98% of travellers recommend
Catamaran Sailing Dolphin/Manatee Watch in Daytona Beach
See all activities in Port Orange

* 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.