Sleepy Hollow Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Sleepy Hollow Vacation
Our vacation packages to Sleepy Hollow give you the power to customize your own adventure. Tailor your getaway to suit your interests and needs and make the most of your time in this interesting city. Gillette Country Club, Energy Capital Sports Complex and Rockpile Museum are just some of the many attractions you'll want to check out during your trip to Sleepy Hollow. Whoever you're taking time off with and whatever your budget, your dream Sleepy Hollow vacation is only clicks away with Expedia.
Ready to book your vacation to Sleepy Hollow?
Sleepy Hollow Hotel Deals
Arbuckle Lodge
1400 South Garner Lake Road Gillette WY
Fully refundableReserve now, pay when you stay
CA $133
CA $147 total
Oct 17 - Oct 18
includes taxes & fees
9.2/10 Wonderful! (1,158 reviews)
"Our room was very clean. We enjoyed the breakfast buffet. My husband had never seen one with biscuits and gravy. Interior main room attractively decorated."
Reviewed on Sep 20, 2026
Days Inn by Wyndham Gillette
910 E Boxelder Road Gillette WY
Fully refundableReserve now, pay when you stay
CA $71
CA $78 total
Sep 23 - Sep 24
includes taxes & fees
8/10 Very good! (922 reviews)
"Clean room and very helpful staff. Breakfast was the bare minimum, which is fine. Housekeeping knocked on our door just before 8 am on the day of check out, which seemed weird and very early for that. Otherwise, the stay was fine overall."
Reviewed on Sep 19, 2026
La Quinta Inn & Suites by Wyndham Gillette
450 E Boxelder Rd Gillette WY
Fully refundableReserve now, pay when you stay
CA $119
CA $131 total
Oct 4 - Oct 5
includes taxes & fees
9.6/10 Exceptional! (1,102 reviews)
"The room was lovely and clean. In addition it was very quiet. The breakfast was incredible. Better than at home. ☺️"
Reviewed on Sep 19, 2026
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 many days is enough for Sleepy Hollow?
Usually, a handful of days is enough to see the major attractions during your Sleepy Hollow vacation. However, if you'd like to have time to unwind or take day tours, consider extending your itinerary.
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?
- 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.
- 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.
- 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.
- Bundle your accommodations and airfare: Once you've nailed down your dates and duration, book the perfect Sleepy Hollow vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
