Sleepy Hollow Vacations from $220

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Your Sleepy Hollow Vacation

Booking a tailor-made Sleepy Hollow vacation package is a good way to know the ins and outs of this neighborhood. From its hot spots to its little-known delights, there's a lot to delve into. Hoping to head out and see the sights during your trip to Sleepy Hollow? Be sure to stop by nearby attractions like Go-Kart City, Port Orange Sport Complex and First United Methodist Church of Port Orange. Don't just dream it — do it! Reserve your ultimate Sleepy Hollow vacation with Expedia and travel your way.

The Latest Sleepy Hollow Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Price was $568, price is now $220 per person
$220
per person
Jan 4 - Jan 9
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
9/10 Wonderful! (1,681 reviews)
The parking and resorts fees cost more than any 5 star Hotel and this is no five star resort. Again get insurance on your trip or pay triple to move to different place. Its not really set up for events. And say no to eighth floor it smells.

Reviewed on Nov 30, 2025

Residence Inn by Marriott Daytona Beach Oceanfront

Residence Inn by Marriott Daytona Beach Oceanfront

3 out of 5
Price was $1,374, price is now $478 per person
$478
per person
Jan 30 - Feb 4
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
The outside of the building could use some tlc but inside was clean and updated. Staff was attentive, polite, & helpful. Breakfast was surprisingly better than I anticipated with hot options outside of the traditional continental options. Furniture around pool was pressure washed every morning and plentiful. There are no seating options for the beach however we would definitely stay here again.

Reviewed on Nov 30, 2025

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was $1,092, price is now $495 per person
$495
per person
Feb 4 - Feb 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.2/10 Wonderful! (2,232 reviews)
Great staff, great location. Very clean. I would definatelly stay here again!

Reviewed on Nov 30, 2025

I-Drive Hotel at Universal

I-Drive Hotel at Universal

2.5 out of 5
International Drive District
Price was $645, price is now $294 per person
$294
per person
Jan 25 - Jan 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
6.8/10 (1,002 reviews)
The staff was very polite. All the facilities worked. Breakfast was good. If you are on a budget, will not find a better hotel than this.

Reviewed on Nov 27, 2025

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $1,229, price is now $568 per person
$568
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (500 reviews)
No Beach view but beach is an10m walk so not too bad. Beach chairs falling apart. The pools and tiki bar were awesome. The two room suite was okay and for the most part pretty clean. But there were some dead bugs which is not what I expected for the price point.

Reviewed on Nov 6, 2025

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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

If you're looking for some top things to see and do in Fly In Spruce Creek and surrounding area, you can visit Spruce Creek Country Club and Crane Lakes Golf and Country Club.

Find hotels in Fly In Spruce Creek

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
$101 nightly
The price is $114 total per night from Dec 30 to Dec 31
$114 total
Dec 30 - Dec 31
Total with taxes and fees
7.2/10 Good! (5,074 reviews)
Staff was really great. Room has the most beautiful view. Really enjoyed the stay.

Reviewed on Nov 29, 2025

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
$157 nightly
The price is $176 total per night from Dec 1 to Dec 2
$176 total
Dec 1 - Dec 2
Total with taxes and fees
9.2/10 Wonderful! (4,172 reviews)
I loved everything about this hotel! The room decor was beachy and cozy! The bathroom was huge! Front desk staff were awesome and the bartender was top notch!

Reviewed on Nov 26, 2025

Daytona Grande Oceanfront Resort
Hard Rock Hotel Daytona Beach

Hard Rock Hotel Daytona Beach

4 out of 5
918 N Atlantic Ave. Daytona Beach FL
Fully refundableReserve now, pay when you stay
$177 nightly
The price is $194 total per night from Dec 7 to Dec 8
$194 total
Dec 7 - Dec 8
Total with taxes and fees
9/10 Wonderful! (1,616 reviews)
Room was very clean, very quiet, easily accessible. Very pleasant atmosphere

Reviewed on Nov 24, 2025

Hard Rock Hotel Daytona Beach
See all 7,534 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Sleepy Hollow

Spruce Creek Country Club featuring signage and a garden

Spruce Creek Country Club

Play a round of golf at Spruce Creek Country Club and enjoy other activities in Samsula-Spruce Creek such as biking. Stroll along the seaside in this family-friendly area, or check out its lively bars.

Spruce Creek Country Club
The ruins of this pre Civil War plantation are now maintained as a free to visit botanical garden. This was the last hibiscus flower and I had to get it’s close up!

Sugar Mill Botanical Gardens

Explore the lovely green spaces of Sugar Mill Botanical Gardens and also enjoy the biking trails in Port Orange. Stroll along the waterfront or discover the beautiful sunrises in this family-friendly area.

Sugar Mill Botanical Gardens

Crane Lakes Golf and Country Club

Play a round of golf at Crane Lakes Golf and Country Club and enjoy other activities in Port Orange such as biking. Attend a sporting event or discover the beautiful sunrises in this family-friendly area.

Crane Lakes Golf and Country Club

Things to do

Courses are not too easy, but not too hard, just right for recreational fun.

Zipline Adventure through Tuscawilla Park

$59
per adult
84% of travellers recommend
Zipline Adventure through Tuscawilla Park
Discovery Dolphin Boat Tour

Discovery Dolphin Boat Tour

$35
per adult
Discovery Dolphin Boat Tour
Segway Beach Ride in Daytona Beach

Segs On The Beach Segway Cruise

$69
per adult
100% of travellers recommend
Segs On The Beach Segway Cruise
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.