Sleepy Hollow Holiday Rentals

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Holiday Rentals in Sleepy Hollow

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
The price is AU$639
includes taxes & fees
19 Oct - 20 Oct
King bed Crystal Lake Mchenry Cary Cozy
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
9.4 out of 10, Exceptional, (30)
"Our stay was great. Had an issue with the breaker but was able to get a hold of the host and fix the issue with no problems. "
The price is AU$438
includes taxes & fees
20 Oct - 21 Oct
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
Hip Urban Loft-Small Town Charm -124 LOFTS #4
10.0 out of 10, Exceptional, (11)
"The loft is a great place to stay and we can’t wait to return! "
The price is AU$327
includes taxes & fees
20 Oct - 21 Oct
Hip Urban Loft-Small Town Charm -124 LOFTS #4
The Tailor House
10.0 out of 10, Exceptional, (46)
"As advertized. Cozy and clean. Good food near by."
The price is AU$450
includes taxes & fees
28 Oct - 29 Oct
The Tailor House
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
9.6 out of 10, Exceptional, (21)
"Nice little apartment. We enjoyed our stay. We even enjoyed the setting area outside."
The price is AU$418
includes taxes & fees
2 Nov - 3 Nov
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
- Fully-Equipped Condo - King Bed - Massive yard -
10.0 out of 10, Exceptional, (34)
"Nice place. Just close enough to walk to 3rd Street. Comfortable beds. Would stay again."
The price is AU$432
includes taxes & fees
22 Oct - 23 Oct
- Fully-Equipped Condo - King Bed - Massive yard -
✽ Charming Cottage ✽ close to College/Town/Station
10.0 out of 10, Exceptional, (51)
"We loved how cute this house was! It was very convenient for visiting our daughter and nice to have plenty of space and amenities. Our host was very prompt communication. Would definitely stay here again!"
The price is AU$470
includes taxes & fees
27 Oct - 28 Oct
✽ Charming Cottage ✽ close to College/Town/Station
- Beautiful Condo - King Bed - Free Waffle Breakfast -
10.0 out of 10, Exceptional, (17)
"A wonderful stay!! Good location. Very clean. Well stocked with everything we needed to enjoy ourselves! So many little touches made it a really nice place to stay. Comfortable and charming! "
The price is AU$399
includes taxes & fees
20 Oct - 21 Oct
- Beautiful Condo - King Bed - Free Waffle Breakfast -
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra
9.6 out of 10, Exceptional, (7)
"The place was just like it was described and it’s pictures. Clean, cozy, and in a nice quiet area. Would stay again! "
The price is AU$427
includes taxes & fees
3 Nov - 4 Nov
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra
Riverfront rental
9.8 out of 10, Exceptional, (32)
"Luci was an excellent host and our stay was great!"
The price is AU$393
includes taxes & fees
26 Oct - 27 Oct
Riverfront rental
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
2.0 star property
10.0 out of 10, Exceptional, (1)
"Super comfy for families and the nicest host. "
The price is AU$833
includes taxes & fees
20 Oct - 21 Oct
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
Little Fox Cottage - A Cozy Riverview Getaway
10.0 out of 10, Exceptional, (15)
"Really great place, the host thought of all the little things you would need which really makes it home away from home!"
The price is AU$359
includes taxes & fees
20 Oct - 21 Oct
Little Fox Cottage - A Cozy Riverview Getaway
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
10.0 out of 10, Exceptional, (2)
"Barrington was an adorable town tucked away just an hour out of Chicago. This property is the perfect spot for a getaway with your loved one. My boyfriend and I had an amazing weekend and will definitely stop by again in the future!"
The price is AU$329
includes taxes & fees
29 Oct - 30 Oct
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Chic 4BR Escape w/ Game Room – LCP Collection
2.0 star property
The price is AU$848
includes taxes & fees
20 Oct - 21 Oct
Chic 4BR Escape w/ Game Room – LCP Collection
The Main Event Game House on the Huntley Square!
9.8 out of 10, Exceptional, (18)
"Beautiful, accommodating, activities for all ages"
The price is AU$459
includes taxes & fees
21 Oct - 22 Oct
The Main Event Game House on the Huntley Square!
Spacious Ranch blocks away from downtown McHenry
9.8 out of 10, Exceptional, (16)
"Very nice place and host is great "
The price is AU$508
includes taxes & fees
23 Oct - 24 Oct
Spacious Ranch blocks away from downtown McHenry
Cozy Outdoor Space + BBQ | LCP Collection
9.0 out of 10, Wonderful, (2)
"Good"
The price is AU$825
includes taxes & fees
10 Nov - 11 Nov
Cozy Outdoor Space + BBQ | LCP Collection
Charming Downtown Farmhouse Apartment #1
10.0 out of 10, Exceptional, (12)
"This place has been done so well. A home away from home, close restaurants, beautiful walking friendly neighborhood. Can’t wait to return. "
The price is AU$379
includes taxes & fees
20 Oct - 21 Oct
Charming Downtown Farmhouse Apartment #1
Modern Suburban Oasis- 14 guest House. Family Friendly!
10.0 out of 10, Exceptional, (1)
The price is AU$1,692
includes taxes & fees
20 Oct - 21 Oct
Modern Suburban Oasis- 14 guest House. Family Friendly!
Just remodeled apartment close to airport and mall
10.0 out of 10, Exceptional, (14)
"Location was close to airport, restaurants and shopping"
The price is AU$397
includes taxes & fees
26 Oct - 27 Oct
Just remodeled apartment close to airport and mall
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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Top Sleepy Hollow Hotel Reviews

Find out more about Sleepy Hollow

Everything you need to know about Sleepy Hollow holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sleepy Hollow holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sleepy Hollow holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Sleepy Hollow holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sleepy Hollow. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sleepy Hollow holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sleepy Hollow holiday rentals we have selected for you start as low as AU$329 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Sleepy Hollow rentals

At Expedia, we put the best Sleepy Hollow holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Sleepy Hollow rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sleepy Hollow holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sleepy Hollow. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Sleepy Hollow?

Yes, there are holiday rentals close to the most popular sights in Sleepy Hollow, or you can select a more secluded option if you're looking for a relaxing stay. Sleepy Hollow is known for its bars.

What are some of the best holiday rentals that Sleepy Hollow has to offer?

Fox River/Chain of Lakes Waterfront Home with Hot Tub: This holiday home rental outside of Sleepy Hollow is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What’s there to see and do in Sleepy Hollow?

While exploring the area, visit family-friendly sights like Santa's Village, or get outside and enjoy nature at Elgin Sports Complex. In the wider area, you’ll find Randall Oaks Golf Club and Hemmens Cultural Center.

What’s a holiday rental in Sleepy Hollow like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sleepy Hollow. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for family trips.