Sleepy Hollow Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 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
Top hotels in Sleepy Hollow
Arbuckle Lodge
1400 South Garner Lake Road Gillette WY
Fully refundableReserve now, pay when you stay
S$133
7 Oct - 8 Oct
includes taxes & fees
9.2/10 Wonderful! (1,152 reviews)
"With the exception that they ran out of several foods before 8:30am on our second morning our stay was great. Rooms are spacious and you get all the feels of welcome home"
Reviewed on 12 Sept, 2026
Days Inn by Wyndham Gillette
910 E Boxelder Road Gillette WY
Fully refundableReserve now, pay when you stay
S$71
14 Sept - 15 Sept
includes taxes & fees
8/10 Very good! (903 reviews)
"WiFi showed available but could not connect. There were several pieces of hair in our bed when we arrived. Otherwise it was ok."
Reviewed on 10 Sept, 2026
Wingate by Wyndham Gillette
1801 Cliff Davis Dr. Gillette WY
Fully refundableReserve now, pay when you stay
S$123
11 Oct - 12 Oct
includes taxes & fees
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?
Offering great value package deals on Expedia, you'll be surprised at how little a holiday to Sleepy Hollow costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Sleepy Hollow?
January, February and March are great times to search for cheap Sleepy Hollow holiday packages. Choosing to travel in quieter periods means you can generally find lower prices on hotels and flights.
How many days is enough for Sleepy Hollow?
The ideal length of your Sleepy Hollow holiday depends on what you'd like to do. Usually, a handful of days to a week will give you time to check out all the main attractions and explore some hidden treasures along the way.
How to find the best Sleepy Hollow package deals?
Use Expedia's filter tool to find some of the best Sleepy Hollow package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Sleepy Hollow package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your holiday package well in advance.
Is it cheaper to book a Sleepy Hollow holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging flights and accommodation individually. Better still, you can personalise your Sleepy Hollow getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a holiday package to Sleepy Hollow?
If you're planning a spur-of-the-moment Sleepy Hollow getaway, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Sleepy Hollow?
- Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Sleepy Hollow.
- Work out your budget: Make sure you have enough money to cover everything from transportation and meals to flights and experiences. Your accommodation will probably be the biggest expense during your trip to Sleepy Hollow.
- Work out your trip length: Consider how long you want to spend exploring Sleepy Hollow. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
- Combine your airfare and accommodation: After you've settled on your trip dates and duration, lock in the ideal Sleepy Hollow holiday package for you.
* 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.
