Sleepy Hollow Holidays

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  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

Top hotels in Sleepy Hollow

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 S$134 per night from 30 Jul to 31 Jul
S$134
30 Jul - 31 Jul
includes taxes & fees
9.2/10 Wonderful! (1,120 reviews)
"The hotel was nice. It seemed that the majority of the guests were on the same floor. The hallways were not carpeted. Noisy. It was a good place for an overnight stay."

Reviewed on 28 Jul, 2026

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 S$97 per night from 1 Aug to 2 Aug
S$97
1 Aug - 2 Aug
includes taxes & fees
Days Inn by Wyndham Gillette
La Quinta Inn & Suites by Wyndham Gillette

La Quinta Inn & Suites by Wyndham Gillette

3 out of 5
450 E Boxelder Rd Gillette WY
Fully refundableReserve now, pay when you stay
The price is S$161 per night from 2 Aug to 3 Aug
S$161
2 Aug - 3 Aug
includes taxes & fees
La Quinta Inn & Suites by Wyndham Gillette
See all 50 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?
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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.