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Top Holiday Rentals in Sleepy Hollow

WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (188)
"ITS A VERY NICE AND UPBEAT ESTABLISHMENT.......I ENJOYED THE STAY ONLY THING I DIDNT LIKE WAS THERE HOUSE KEEPING SCHEDULE BUT OTHER THAN THAT ITS A NICE QUIET LOCATION WITH NICE PEOPLE"
The price is £75
includes taxes & fees
5 Jun - 6 Jun
WoodSpring Suites Chicago Addison
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, (9)
"Great location with two master suites with king beds. Breakfast buffet was good. Next time I will request first floor as there is no elevator."
The price is £169
includes taxes & fees
3 Jun - 4 Jun
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
9.8 out of 10, Exceptional, (24)
"The house is so big and beautiful, and we enjoyed our weekend staying there, thank you."
The price is £2,147
includes taxes & fees
27 Jun - 28 Jun
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
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Game room/King Bed /Wi-Fi/Deck + Fire Pit
10.0 out of 10, Exceptional, (14)
"Relaxing, quiet and clean neighborhood. Love the retro decor. Kitchen is well equipped for those that might want to cook. A few branches were down in backyard, furniture wasn't set out yet such as outdoor dining table and chairs or gazebo, but overall property was in good condition. Thank you for a relaxing place to stay."
The price is £342
includes taxes & fees
3 Jun - 4 Jun
Game room/King Bed /Wi-Fi/Deck + Fire Pit
Riverfront rental with fun activities
10.0 out of 10, Exceptional, (18)
"Cozy with lots of beds. A great pick for patio gathering and fun at the river. place was clean and had lots of little amenities on site."
The price is £227
includes taxes & fees
3 Jun - 4 Jun
Riverfront rental with fun activities
Glen Ellyn Country Side Home
9.4 out of 10, Exceptional, (9)
"This place was great. So much space, it was clean and super quiet area. It was close to everything we needed and our host responded within minutes of request. If you have kids tons of space with pool. We travel year round coast to coast for lacrosse tournaments using vrbo. This house by far one of the best. We will be back!"
Glen Ellyn Country Side Home
Modern Open Concept Home with Pool Table by Train Station
9.4 out of 10, Exceptional, (11)
"The home was very comfortable - it was modern and the beds were good. Unfortunately the repairs to make it rentable were not high quality. The bathroom sink in the half bath was leaking when we arrived. The door frame of the basement bathroom had fallen off & was lying on the floor when we arrived. The shower door in the upstairs bathroom would not stay on the track. However , none of these problems would deter me from renting again. They were just inconveniences."
Modern Open Concept Home with Pool Table by Train Station
Fox Valley Farmhouse Overlooking The Fox River!
10.0 out of 10, Exceptional, (23)
"We had a wonderful stay! Beautiful home and extremely clean. Close location to both downtown St. Charles and Geneva shopping and restaurants. The host was very friendly and helpful with suggestions and the check in/check out process was beyond easy. Would recommend 100% and hope to be back again someday!"
Fox Valley Farmhouse Overlooking The Fox River!
✽ Charming Cottage ✽ close to College/Town/Station
10.0 out of 10, Exceptional, (31)
"Great house thank you"
The price is £235
includes taxes & fees
25 Jun - 26 Jun
✽ Charming Cottage ✽ close to College/Town/Station
Fox River Retreat
9.6 out of 10, Exceptional, (5)
"Very understanding owner "
Fox River Retreat
Great Amenities Onsite! Pool, Private Parking, Free Breakfast, Close to Legoland
8.0 out of 10, Very good, (2)
"We enjoyed our stay with plenty of space for two couples. Separate bedrooms/baths were perfect. Furnature in the living room needs updating."
The price is £183
includes taxes & fees
3 Jun - 4 Jun
Great Amenities Onsite! Pool, Private Parking, Free Breakfast, Close to Legoland
Historic home with easy access to Chicago
9.6 out of 10, Exceptional, (152)
"Lots of space"
Historic home with easy access to Chicago
Breathtaking home close to Schaumburg, Chicago
9.8 out of 10, Exceptional, (37)
"It was a perfect location and plenty of space for family of 8 plus visiting friends. Mike was a great host and we got to enjoy some firewood he had set up for us to have a fire. Highly recommend! The description says 4 bathrooms and there are 3 bathrooms…the only discrepancy."
Breathtaking home close to Schaumburg, Chicago
Spacious open concept home w/ game room + firepit
9.8 out of 10, Exceptional, (38)
"great house to relax and be together with the family."
Spacious open concept home w/ game room + firepit
Peaceful and Relaxing Water Front Home with Outdoor Pool Sleeps 12
9.8 out of 10, Exceptional, (9)
"We stayed at this property for 6 nights to celebrate the Thanksgiving holiday with my family. The property was clean, well maintained, and had every cooking equipment that we needed. We had a terrific time."
Peaceful and Relaxing Water Front Home with Outdoor Pool Sleeps 12
Log Cabin with HGTV Style Backyard INCREDIBLE property
8.2 out of 10, Very good, (16)
"Perfect amount of space for adults wanting to hang out, but not be on top of each other. Very relaxing. Would go back!"
Log Cabin with HGTV Style Backyard INCREDIBLE property
Pet-Friendly Bartlett Farmhouse w/ Deck!
9.4 out of 10, Exceptional, (3)
"Well equipped. Lots of amenities, farmhouse ambience, comfortable beds. Good location."
Pet-Friendly Bartlett Farmhouse w/ Deck!
Comforting Retreat Near Woodfield Mall by RedAwning
10.0 out of 10, Exceptional, (5)
"Clean, nice place"
Comforting Retreat Near Woodfield Mall by RedAwning
House with great location!
10.0 out of 10, Exceptional, (12)
"Alyssa is just amazing. Cannot say enough about how great she is. Super accommodating and understanding. When something isn’t right, she will fix it!"
The price is £212
includes taxes & fees
30 Jun - 1 Jul
House with great location!
St. Charles Riverview Retreat
10.0 out of 10, Exceptional, (8)
"Close to a nice walking trail by the Fox river. Stairs are a bit steep, but one bedroom is on the main floor."
The price is £367
includes taxes & fees
1 Jul - 2 Jul
St. Charles Riverview Retreat
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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.

Sleepy Hollow Holiday Rental Travel Info

Other types of properties in Sleepy Hollow you may be interested in

Hyatt Regency Schaumburg Chicago
4.0 star property
8.0 out of 10, Very good, (1008)
"I like the actual room. It was spacious. I was glad Wi-Fi was free. However, the cabinet door for the cabinet that held the safe was off it's hinges and fell off just from being touched. There was also an unused mini-fridge in the closet, don't understand why that was there. Also, there was no Do Not Disturbed sign available and I had to request one. I was surprised the buffet cost money. I originally thought it was free."
The price is £107
includes taxes & fees
2 Jul - 3 Jul
Hyatt Regency Schaumburg Chicago
Best Western O'Hare/Elk Grove Hotel
3.0 star property
8.2 out of 10, Very good, (1003)
"I booked through Expedia and i found the communication from the hotel to be great. I received a text explaining how to activate shuttle ride from the airport, along with explanation on where to meet the driver. I will say they might need to update those instructions as it was slightly different than what desk clerk told me when i called to let them know i had arrived. I appreciated the text. Breakfast was varied, with some hot items (eggs, potatoes, sausage) and i liked that they had some...
The price is £77
includes taxes & fees
2 Jun - 3 Jun
Best Western O'Hare/Elk Grove Hotel
Motel 6 Rolling Meadows, IL - Chicago Northwest
2.0 star property
6.6 out of 10, (1005)
"Okay"
The price is £50
includes taxes & fees
6 Jun - 7 Jun
Motel 6 Rolling Meadows, IL - Chicago Northwest
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.

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 £75 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?

Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking: This holiday home rental outside of Sleepy Hollow is located in the city centre, and offers a BBQ, air conditioning and cable TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 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.

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