Sleepy Hollow Vacations from $415

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Your Sleepy Hollow Vacation

Our vacation packages to Sleepy Hollow provide countless opportunities to enjoy new sights, sounds and flavors. And with all the details worked out, you can breathe easy and enjoy your city break without a worry in the world. Every trip to Sleepy Hollow should include some sightseeing. Bond Falls is a popular place to start your exploring. Browse Expedia's extensive range of travel options and start planning your dream vacation to Sleepy Hollow today.

The Latest Sleepy Hollow vacation packages

Price found within the past 48 hours. Click for updated prices.
Love Hotels Silver Street by OYO at Hurley WI

Love Hotels Silver Street by OYO at Hurley WI

2.5 out of 5
per person
Oct 4 - Oct 8
found 12 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Ironwood (IWD)
5.2/10 (107 reviews)
there was a disagreement in the parking lot shortly after we arrived.

Reviewed on Jun 25, 2025

AmericInn by Wyndham Silver City

AmericInn by Wyndham Silver City

2.5 out of 5
per person
Oct 4 - Oct 8
found 12 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Ironwood (IWD)
9/10 Wonderful! (904 reviews)
Great location. On-site restaurant has an extensive menu with great service and wonderful lake views. Breakfast included was much greater than a normal continental breakfast.

Reviewed on Jul 14, 2025

Days Inn by Wyndham Hurley

Days Inn by Wyndham Hurley

2 out of 5
per person
Oct 4 - Oct 8
found 12 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Ironwood (IWD)
8.4/10 Very Good! (832 reviews)
It was a overnight stop, worked well in our travel plans.

Reviewed on Jul 6, 2025

Quality Inn

Quality Inn

2.5 out of 5
per person
Oct 4 - Oct 8
found 12 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Ironwood (IWD)
8.6/10 Excellent! (488 reviews)
Our family stayed here and it was decent. The breakfast was good with waffles, eggs, sausage, and several other options.

Reviewed on Jul 7, 2025

AmericInn by Wyndham Ironwood

AmericInn by Wyndham Ironwood

2.5 out of 5
per person
Oct 4 - Oct 8
found 12 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Ironwood (IWD)
9/10 Wonderful! (689 reviews)
On arrival they said I had no reservation. Even after showing my confirmation number. She said That Expedia had not sent it over. So we had to wait Otherwise nice place.

Reviewed on Jul 7, 2025

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Discover the most popular places to visit in Sleepy Hollow

Beautiful falls with many opportunities for unique photos throughout the year.

Bond Falls

5/5(1 review)

Commune with nature and explore the great outdoors at Bond Falls during your travels in Bruce Crossing. Wander the forest or discover the area's waterfalls.

Bond Falls

Paulding Light

5/5(2 reviews)

You can learn about the history of Bruce Crossing with a trip to Paulding Light. Wander the forest or discover the area's waterfalls.

Paulding Light

Sleepy Hollow Hotel Deals

Two Rivers Motel and Cabins
Two Rivers Motel and Cabins
2 out of 5
2920 Old M28, Trout Creek, MI
9.6/10 Exceptional! (29 reviews)
"Good Wi-FI, microwave and Mini-Fridge."

Reviewed on Jul 3, 2025

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Two Rivers Motel and Cabins
Rustic Cozy Cottage! Snowmobile,ATV Trails, Bond & Agate Falls, Bruce Crossing!
Rustic Cozy Cottage! Snowmobile,ATV Trails, Bond & Agate Falls, Bruce Crossing!
Trout Creek
9.8/10 Exceptional! (118 reviews)
Just as advertised
"Liked the small town and out of the way location. It is on a main highway which allowed us to easily drive everywhere. Bond Falls is a must see and is only a few minutes drive."

Reviewed on Jul 11, 2025

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Rustic Cozy Cottage! Snowmobile,ATV Trails, Bond & Agate Falls, Bruce Crossing!
Come Stay Off-Grid in Michigan's Beautiful Upper Peninsula
Come Stay Off-Grid in Michigan's Beautiful Upper Peninsula
Bruce Crossing
10/10 Exceptional! (7 reviews)
Great little place, Great hosts
"Nice, relaxing property that is centrally located to resultants, hiking, and exploring the Upper Peninsula. Hosts were very responsive, bed was cozy, front porch was perfect and the fire pit made the stay a place to create memories during the evening hours."

Reviewed on Jul 9, 2025

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Come Stay Off-Grid in Michigan's Beautiful Upper Peninsula
See all 96 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.

Find the Best Sleepy Hollow Vacation Packages

Sleepy Hollow Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Sleepy Hollow vacation package cost?
Offering great value package deals from $415 on Expedia, you'll be surprised at how little a vacation to Sleepy Hollow costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Sleepy Hollow?
You can generally find reduced prices and greater availability in October, November and December. Take a look at our cheap Sleepy Hollow vacation packages and you could get some great off-season discounts.
How many days is enough for Sleepy Hollow?
The ideal duration for your Sleepy Hollow vacation depends on what you'd like to see and do. Generally, a handful of days to a week will give you plenty of time to visit all the major attractions and explore some hidden spots along the way.
How to find the best Sleepy Hollow package deals?
Use Expedia's filters to find some tempting Sleepy Hollow package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Sleepy Hollow package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Sleepy Hollow vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking stays and flights separately. Better still, you can customize your Sleepy Hollow trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Sleepy Hollow?
If you have your Sleepy Hollow travel dates confirmed, book as early as you can to grab some fantastic deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for traveling on a whim.
How to plan a trip to Sleepy Hollow?

  1. Choose when to travel: Check your calendar and get packing. Your favorite time of year and the activities on offer will also help you decide when to visit Sleepy Hollow.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and food to airfares and activities. Your accommodations will likely be the largest expense during your trip to Sleepy Hollow.
  3. Explore Sleepy Hollow with our trip planning tool: Gain insights into the most popular attractions and best stays for your trip to Sleepy Hollow. You can also save your favorite locations, collaborate with family and friends and manage your plans in one place.
  4. Decide how long to go for: Now that you know more about Sleepy Hollow, you can figure out the perfect length of your break. Pull together a rough plan and allocate enough time for all the things you want to do.
  5. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored Sleepy Hollow vacation package.
  6. Book any day trips or activities: Now to the fun part --- organizing everything you want to do and see. Check out some of the top things to do in Sleepy Hollow and reserve your tickets early to save time (and maybe some money too!).

Does Expedia offer Book Now, Pay Later Sleepy Hollow vacation packages?
If you're like us, you love discovering new places but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Sleepy Hollow break over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.