Sleepy Hollow Vacations from $719

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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.

The Latest Sleepy Hollow vacation packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Gillette

Days Inn by Wyndham Gillette

2 out of 5
Price was $1,085, price is now $719 per person
$719
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Houston (IAH) to Gillette (GCC)
8.2/10 Very Good! (569 reviews)
Great value and great staff.

Reviewed on Sep 1, 2025

Summit Suites

Summit Suites

2.5 out of 5
Price was $1,201, price is now $789 per person
$789
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Houston (IAH) to Gillette (GCC)
9/10 Wonderful! (498 reviews)
Nice stay, quiet and comfortable and good breakfast options. Would stay here again.

Reviewed on Sep 1, 2025

Howard Johnson by Wyndham Gillette

Howard Johnson by Wyndham Gillette

2 out of 5
Price was $1,093, price is now $725 per person
$725
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Houston (IAH) to Gillette (GCC)
6.8/10 (659 reviews)
Good hotel, I would stay again.

Reviewed on Aug 29, 2025

Baymont by Wyndham Gillette

Baymont by Wyndham Gillette

2.5 out of 5
Price was $1,106, price is now $744 per person
$744
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Houston (IAH) to Gillette (GCC)
7.2/10 Good! (377 reviews)
This hotel seems to be in the process of being updated, and overall, it was a pleasant and clean place to stay. The room was comfortable, amenities were solid, and the continental breakfast was decent. It was an affordable and convenient stop during our long road trip. We were satisfied with our stay and appreciated the cleanliness and value.

Reviewed on Aug 11, 2025

Red Lion Hotel Gillette

Red Lion Hotel Gillette

3 out of 5
Price was $1,094, price is now $736 per person
$736
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Houston (IAH) to Gillette (GCC)
6/10 (209 reviews)
Nice place, good breakfast.

Reviewed on Sep 2, 2025

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Discover the most popular places to visit in Sleepy Hollow

CAM-PLEX Multi-Event Facilities

You can make plans for a show at CAM-PLEX Multi-Event Facilities during your trip to Gillette. While in this family-friendly area, you can savor the top-notch restaurants.

CAM-PLEX Multi-Event Facilities

Eagle Butte Coal Mine

Find out about the history of Gillette when you spend time at Eagle Butte Coal Mine. While in this family-friendly area, you can savor the top-notch restaurants.

Eagle Butte Coal Mine

Gillette Country Club

Enjoy a round of golf in Gillette at Gillette Country Club. While in this family-friendly area, you can savor the top-notch restaurants.

Gillette Country Club

Sleepy Hollow Hotel Deals

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
$51 nightly
The price is $56 total per night from Sep 7 to Sep 8
$56 total
Sep 7 - Sep 8
Total with taxes and fees
Days Inn by Wyndham Gillette
Arbuckle Lodge

Arbuckle Lodge

3 out of 5
1400 South Garner Lake Road, Gillette, WY
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $108 total per night from Sep 7 to Sep 8
$108 total
Sep 7 - Sep 8
Total with taxes and fees
Arbuckle Lodge
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
$91 nightly
The price is $100 total per night from Sep 21 to Sep 22
$100 total
Sep 21 - Sep 22
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Gillette
See all 45 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.

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Frequently asked questions

How much does a Sleepy Hollow vacation package cost?
Offering great value package deals from $719 on Expedia, you'll be surprised at how little a vacation to Sleepy Hollow costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Sleepy Hollow?
You can typically find lower rates and better availability in February, November and December. Explore our cheap Sleepy Hollow vacation packages and you could get some great off-season deals.
How many days is enough for Sleepy Hollow?
The ideal length for your Sleepy Hollow vacation depends on what you'd like to see and do. Usually, a handful of days to a week will give you enough time to hit all the leading attractions and explore some hidden spots 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 vacation package well in advance.
Is it cheaper to book a Sleepy Hollow vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and accommodations individually. Better still, you can personalize 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 vacation 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.
Does Expedia offer Book Now, Pay Later Sleepy Hollow vacation packages?
Set off on your dream trip to Sleepy Hollow with help from Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait for payday — we've joined forces with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans let you spread the cost over 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily stick to your budget and snag great deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.