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Holiday Rentals in Sleepy Hollow

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Our top choices for Sleepy Hollow holiday rentals

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Barrington
9.8 out of 10, Exceptional, (10 reviews)
"Very nice little spot... Host was absolutely wonderful!!! Definitely stay here again!"
United States
Adam B.
The price is €157
includes taxes & fees
16 Jun - 17 Jun
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

Just remodeled apartment close to airport and mall

Just remodeled apartment close to airport and mall
Elk Grove Village
10.0 out of 10, Exceptional, (16 reviews)
"Great place! "
United States
Isabella T.
The price is €223
includes taxes & fees
15 Jun - 16 Jun
Just remodeled apartment close to airport and mall

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (68 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is €276
includes taxes & fees
24 Jun - 25 Jun
✽ Charming Cottage ✽ close to College/Town/Station

King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is €391
includes taxes & fees
15 Jun - 16 Jun
King bed Crystal Lake Mchenry Cary Cozy

Kildahl House - Boutique Farmhouse Suite #4

Kildahl House - Boutique Farmhouse Suite #4
West Dundee
10.0 out of 10, Exceptional, (16 reviews)
"Wonderful place to stay and the host was very welcoming and easy to work with!"
United States
Kevin B.
The price is €231
includes taxes & fees
14 Jun - 15 Jun
Kildahl House - Boutique Farmhouse Suite #4

Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry

Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
Geneva
9.4 out of 10, Exceptional, (26 reviews)
"Nice little apartment. We enjoyed our stay. We even enjoyed the setting area outside."
United States
Jerilynn L.
The price is €273
includes taxes & fees
15 Jun - 16 Jun
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry

Chic 1BR Apt -Arlington Heights

Chic 1BR Apt -Arlington Heights
Arlington Heights
8.0 out of 10, Very good, (1 review)
"Parking was a problem "
United States
Brian W.
Chic 1BR Apt -Arlington Heights

Spacious 3 Bedroom

Spacious 3 Bedroom
Cary
The price is €311
includes taxes & fees
17 Jun - 18 Jun
Spacious 3 Bedroom

Little Fox Cottage - A Cozy Riverview Getaway

Little Fox Cottage - A Cozy Riverview Getaway
Fox River Grove
10.0 out of 10, Exceptional, (18 reviews)
"Host and amenities were great!"
United States
Jeff P.
The price is €218
includes taxes & fees
15 Jun - 16 Jun
Little Fox Cottage - A Cozy Riverview Getaway

124 Lofts #3 - Downtown Dundee - Walk to Dining

124 Lofts #3 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (22 reviews)
"We were in town visiting family and it was the perfect spot to stay for a day or two. We loved that it was right above a local cafe (which was also fantastic by the way!!), and the check-in/out process was a breeze! Owner was very communicative, would definitely stay here again!"
United States
Adamm I.
The price is €213
includes taxes & fees
21 Jun - 22 Jun
124 Lofts #3 - Downtown Dundee - Walk to Dining

Riverfront rental

Riverfront rental
South Elgin
10.0 out of 10, Exceptional, (43 reviews)
"Great place to stay near St. Charles/Geneva. Will definitely stay again next time we visit. Plenty of room, great view, super easy access to west suburbs, North Ave./Randal Rd,/25/31, but tucked away from the hustle and bustle etc. Host was great, respected our privacy. Super hot shower! "
United States
Elsa L.
The price is €208
includes taxes & fees
21 Jun - 22 Jun
Riverfront rental

Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain

Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
Geneva
9.4 out of 10, Exceptional, (34 reviews)
"The host was very welcoming "
United States
Karen B.
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain

Great Value 3BR 2.5BA Game Rm Free Park, Safe Area

Great Value 3BR 2.5BA Game Rm Free Park, Safe Area
Carol Stream
9.4 out of 10, Exceptional, (6 reviews)
"The property was nice. Perfect for our guys trip. "
United States
Jay S.
Great Value 3BR 2.5BA Game Rm Free Park, Safe Area

The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (52 reviews)
"Amazing stay. So close to everything!"
United States
Brittany H.
The price is €252
includes taxes & fees
24 Jun - 25 Jun
The Tailor House

Terrific 3-bedroom family-friendly house close to everything in charming McHenry

Terrific 3-bedroom family-friendly house close to everything in charming McHenry
McHenry
8.4 out of 10, Very good, (7 reviews)
"Cute and cozy little house. Convenient location. I would stay there again if the need ever comes up again. "
United States
holly g.
The price is €254
includes taxes & fees
14 Jun - 15 Jun
Terrific 3-bedroom family-friendly house close to everything in charming McHenry

Kildahl House - Boutique Farmhouse Suite #1

Kildahl House - Boutique Farmhouse Suite #1
West Dundee
9.8 out of 10, Exceptional, (15 reviews)
"This is a lovely place to call “home base” while visiting Chicago and surrounding communities. Comfortable, clean, quiet and nicely decorated. My little dogs even had a welcome basket! I wish I could have stayed a bit longer"
United States
Thea
The price is €231
includes taxes & fees
14 Jun - 15 Jun
Kildahl House - Boutique Farmhouse Suite #1

124 Lofts #1 - Downtown Dundee - Walk to Dining

124 Lofts #1 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (17 reviews)
"Great stay. The loft is situated in an area where it is easy to walk to interesting dining options and stroll the river walk."
United States
Angela D.
The price is €213
includes taxes & fees
21 Jun - 22 Jun
124 Lofts #1 - Downtown Dundee - Walk to Dining

The Main Event Game House on the Huntley Square!

The Main Event Game House on the Huntley Square!
Huntley
10.0 out of 10, Exceptional, (21 reviews)
"Our stay was very comfortable and the game room was great for our big family. The kids didn't want to leave and always ask about going back."
United States
BENJAMIN B.
The price is €257
includes taxes & fees
15 Jun - 16 Jun
The Main Event Game House on the Huntley Square!

- Fully-Equipped Condo - King Bed - Massive yard -

- Fully-Equipped Condo - King Bed - Massive yard -
Geneva
10.0 out of 10, Exceptional, (40 reviews)
"Great place, well appointed, worked well for our needs!! Host was very responsive to any questions/requests. "
United States
Amy C.
The price is €323
includes taxes & fees
15 Jun - 16 Jun
- Fully-Equipped Condo - King Bed - Massive yard -

- Beautiful Condo - King Bed - Free Waffle Breakfast -

- Beautiful Condo - King Bed - Free Waffle Breakfast -
Geneva
10.0 out of 10, Exceptional, (27 reviews)
"Lovely home. We had a group of seven adults. The home was super clean, thoughtfully designed for guest comfort and close to downtown. Would stay again!!"
United States
Julie C.
The price is €284
includes taxes & fees
16 Jun - 17 Jun
- Beautiful Condo - King Bed - Free Waffle Breakfast -
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, apart-hotels, 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 favorite 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 depends 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 €157 per night. Entering your travel dates in the search wizard you might find 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?

Breathtaking home close to Schaumburg, Chicago: This holiday home rental outside of Sleepy Hollow offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 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 terrace, a garden and a selection of games 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 Hemmens Cultural Center and Grand Victoria Casino.

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.