Sleepy Hollow Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AEDĀ 5,000 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

Find the Best Sleepy Hollow Vacation Packages

Sleepy Hollow Hotel Deals

Arbuckle Lodge

Arbuckle Lodge

3 out of 5
1400 South Garner Lake Road Gillette WY
Fully refundableReserve now, pay when you stay
The price is AEDĀ 374 per night from Nov 13 to Nov 14
AEDĀ 374
AEDĀ 411 total
13 Nov - 14 Nov
includes taxes & fees
Arbuckle Lodge
Days Inn by Wyndham Gillette

Days Inn by Wyndham Gillette

2 out of 5
910 E Boxelder Road Gillette WY
Fully refundableReserve now, pay when you stay
The price is AEDĀ 178 per night from Nov 18 to Nov 19
AEDĀ 178
AEDĀ 196 total
18 Nov - 19 Nov
includes taxes & fees
8/10 Very Good! (1,006 reviews)
"The room had a comfy bed with nice linens, fridge, and microwave. Had a bathtub with lots of hot water. You could open the window for fresh air and the breakfast had lots of choice. Egg sausage and the regular continental stuff. Staff was very friendly. Carpet and furniture and chair in room was ..."

Reviewed on 12 November 2026

Days Inn by Wyndham Gillette
Summit Suites

Summit Suites

2.5 out of 5
211 Decker Ct Gillette WY
The price is AEDĀ 285 per night from Nov 13 to Nov 14
AEDĀ 285
AEDĀ 314 total
13 Nov - 14 Nov
includes taxes & fees
8.8/10 Excellent! (903 reviews)
"Clean quiet room staff helpful"

Reviewed on 8 November 2026

Summit Suites
See all 52 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 vacation package cost?
You can snap up a vacation package to this top destination on Expedia. However, how much your vacation to Sleepy Hollow costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Sleepy Hollow?
You can usually find reduced prices and greater availability in January, February and March. Browse our cheap Sleepy Hollow vacation packages and you could land some excellent off-season deals.
How to find the best Sleepy Hollow package deals?
Bagging a cheap Sleepy Hollow package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, apply some filters and see what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most economical Sleepy Hollow package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Sleepy Hollow vacation as a package?
You can enjoy significant savings on your Sleepy Hollow retreat by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Sleepy Hollow?
If you're planning a spur-of-the-moment Sleepy Hollow adventure, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Sleepy Hollow?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Sleepy Hollow.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and meals to flights and activities. Your hotel will probably be the largest expense during your trip to Sleepy Hollow.
  3. Decide how long to go away for: Now that you're more familiar with Sleepy Hollow, you can figure out the ideal length of your break. Create a rough itinerary and allocate enough time for all the things you want to do.
  4. Bundle your accommodations and airfare: Once you've nailed down your dates and duration, book the perfect Sleepy Hollow vacation package for you.