Sleepy Hollow Vacations from $1,080

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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.
Davos Chalet

Davos Chalet

2 out of 5
Price was $1,292, price is now $1,080 per person
$1,080
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Augusta (AGS) to Ironwood (IWD)
8.8/10 Excellent! (94 reviews)
It was such a beauitful place to stay especially with the fall colors. There were community snacks including s’mores which was such a great surprise!

Reviewed on Oct 22, 2025

North Star Retreat-kayak I Swim I Snowmobile

North Star Retreat-kayak I Swim I Snowmobile

2 out of 5
Price was $1,773, price is now $1,590 per person
$1,590
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Augusta (AGS) to Ironwood (IWD)
No reviews
Lakeside Haus in Presque Isle

Lakeside Haus in Presque Isle

2 out of 5
Price was $1,731, price is now $1,564 per person
$1,564
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Augusta (AGS) to Ironwood (IWD)
No reviews
Quality Inn Ironwood

Quality Inn Ironwood

2.5 out of 5
Price was $1,280, price is now $1,173 per person
$1,173
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Augusta (AGS) to Ironwood (IWD)
8.6/10 Excellent! (535 reviews)
I do like an elevator when bring in your suitcase up and Ironwood location does not have that. Also, when traveling with another person, I would like to be able to split the room bill between 2 credit cards.

Reviewed on Sep 14, 2025

Days Inn by Wyndham Hurley

Days Inn by Wyndham Hurley

2 out of 5
Price was $1,296, price is now $1,190 per person
$1,190
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Augusta (AGS) to Ironwood (IWD)
8.4/10 Very Good! (892 reviews)
Was a good place to stay, last time we were in however the hottub was out of order and they did not inform us of this before check-in. That was really the only disappointment. Breakfasts were excellent for a Hotel style free breakfast. Room was clean and our stay was quiet.

Reviewed on Oct 20, 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

Teal Wing - Premier Lakeside Lodging on Lake Gogebic

Teal Wing - Premier Lakeside Lodging on Lake Gogebic

Marenisco MI
10/10 Exceptional! (86 reviews)
Teal Wing is a beautiful home with amazing views out all of the windows. It is a very peaceful setting that invites you to relax and glory in the Beauty all around you. We went out on the dock at night to stargaze and we were treated to a magnificent moon rise across the water. We really enjoyed ...

Reviewed on Sep 25, 2025

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Teal Wing - Premier Lakeside Lodging on Lake Gogebic
Lake front cabin close to UTV/ATV and snowmobile trails.

Lake front cabin close to UTV/ATV and snowmobile trails.

Bergland MI
9.6/10 Exceptional! (63 reviews)
Perfect cozy cabin getaway to explore the Porcupine Mountains, Lake of the Clouds, Agate Falls, Bond Falls, ATV trails, and Gogebic Lake!

Reviewed on Oct 27, 2025

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Lake front cabin close to UTV/ATV and snowmobile trails.
The Clinic

The Clinic

Bruce Crossing MI
9.8/10 Exceptional! (29 reviews)
Very nice stay with our group of 6 adults. Spent a long weekend enjoying the local trails and fall colors. Will stay again!!

Reviewed on Oct 8, 2025

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The Clinic
See all 92 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 $1,080 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.