Sleepy Hollow Vacation Rentals

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Check prices for these dates

Tonight
Oct 29 - Oct 30
Tomorrow
Oct 30 - Oct 31
This weekend
Oct 31 - Nov 2
Next weekend
Nov 7 - Nov 9

Vacation Rentals in Sleepy Hollow

A heated pool
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
9.2 out of 10, Wonderful, (41)
"Very comfortable… enjoyed the property to the upmost.."
United States
Debra H.
The price is ￥58,433
￥190,491 total
includes taxes & fees
Nov 3 - Nov 4
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
Paper towels
Just remodeled apartment close to airport and mall
Just remodeled apartment close to airport and mall
10.0 out of 10, Exceptional, (15)
"Location was close to airport, restaurants and shopping"
United States
Dorothy J.
The price is ￥20,543
￥38,581 total
includes taxes & fees
Oct 30 - Oct 31
Just remodeled apartment close to airport and mall
Smart TV
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
10.0 out of 10, Exceptional, (3)
"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!"
United States
Cierra F.
The price is ￥19,173
￥32,395 total
includes taxes & fees
Oct 30 - Oct 31
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
3 bedrooms, desk, iron/ironing board, travel crib
- Beautiful Condo - King Bed - Free Waffle Breakfast -
- Beautiful Condo - King Bed - Free Waffle Breakfast -
10.0 out of 10, Exceptional, (19)
"Beautiful place! Every detail was thought of for their guest!"
United States
Libby M.
The price is ￥14,434
￥38,769 total
includes taxes & fees
Nov 3 - Nov 4
- Beautiful Condo - King Bed - Free Waffle Breakfast -
Outdoor dining
✽ Charming Cottage ✽ close to College/Town/Station
✽ Charming Cottage ✽ close to College/Town/Station
10.0 out of 10, Exceptional, (52)
"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!"
United States
Mary
The price is ￥25,869
￥46,929 total
includes taxes & fees
Nov 3 - Nov 4
✽ Charming Cottage ✽ close to College/Town/Station
Smart TV
Fox Valley Farmhouse Overlooking The Fox River!
Fox Valley Farmhouse Overlooking The Fox River!
10.0 out of 10, Exceptional, (41)
"Amazing place, owner was super responsive, no issues at all and the house was so clean!"
United States
David K.
Fox Valley Farmhouse Overlooking The Fox River!
Microwave, dishwasher, coffee/tea maker, toaster
Spacious open concept home w/ game room + firepit
Spacious open concept home w/ game room + firepit
9.8 out of 10, Exceptional, (73)
"Very spacious home, bedrooms good sized, really liked the game room to keep the kids occupied."
United States
Patricia
Spacious open concept home w/ game room + firepit
Smart TV, books
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
2.0 star property
10.0 out of 10, Exceptional, (2)
"Super comfy for families and the nicest host. "
United States
Anonymous traveler
The price is ￥51,494
￥81,624 total
includes taxes & fees
Oct 30 - Oct 31
Schaumburg Modern 4BR Farmhouse w/ Private Master & Sleeps 9. Families & groups
Fridge, microwave, oven, stovetop
Fox River/Chain of Lakes Waterfront Home with Hot Tub
Fox River/Chain of Lakes Waterfront Home with Hot Tub
10.0 out of 10, Exceptional, (38)
"Loved our stay, stocked kitchen, great backyard and big tub. "
United States
Michael S.
Fox River/Chain of Lakes Waterfront Home with Hot Tub
Fridge, microwave, oven, stovetop
Spacious Ranch blocks away from downtown McHenry
Spacious Ranch blocks away from downtown McHenry
9.8 out of 10, Exceptional, (16)
"Great home and perfect location. "
United States
Steve B.
The price is ￥34,238
￥49,832 total
includes taxes & fees
Nov 9 - Nov 10
Spacious Ranch blocks away from downtown McHenry
4 bedrooms, travel crib, free WiFi, bed sheets
Paradise 4BR w/ Pool & Games
Paradise 4BR w/ Pool & Games
10.0 out of 10, Exceptional, (2)
"Everything was very clean, the location was good. My family and I enjoyed it a lot. Check-in was very easy and everything in the house was very up-to-date."
United States
Dayana O.
Paradise 4BR w/ Pool & Games
Living area
In-ground pool, private! In town location near it all. Updated, Clean!
In-ground pool, private! In town location near it all. Updated, Clean!
10.0 out of 10, Exceptional, (4)
"Accommodating hosts, lovely property and location. Great support for our family visit."
United States
Cha Ron S.
In-ground pool, private! In town location near it all. Updated, Clean!
Private kitchen
Spacious Family & Pet-Friendly Getaway in Lake in the Hills
Spacious Family & Pet-Friendly Getaway in Lake in the Hills
9.0 out of 10, Wonderful, (2)
"The place is much nicer and larger than the pictures show. The basement is full of activities for adults and teens, and with the multiple levels it ensures everyone in the family has space"
United States
Richard M.
Spacious Family & Pet-Friendly Getaway in Lake in the Hills
Exterior
Historic home with easy access to Chicago
Historic home with easy access to Chicago
9.8 out of 10, Exceptional, (172)
"A truly memorable stay. I booked this home for a bridal party I was in and the home was perfect for all of us to connect together and relax in between wedding events. One of the best Vrbos I’ve stayed. Would love to come back "
United States
Samantha L.
Historic home with easy access to Chicago
Property grounds
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
9.0 out of 10, Wonderful, (4)
"Everything was as described. House was very spacious and comfortable. This was a work trip but it was a nice place to relax in the evening. Enjoyed the back yard and grilling out for dinner. Would definitely stay here again. Kevin "
United States
James b.
The price is ￥29,399
￥70,359 total
includes taxes & fees
Nov 3 - Nov 4
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Fridge, microwave, oven, stovetop
Bliss in Batavia near the Fox River
Bliss in Batavia near the Fox River
9.8 out of 10, Exceptional, (24)
"We had a lot of fun and the house was nice! "
United States
Karsten Z.
The price is ￥41,771
￥84,587 total
includes taxes & fees
Nov 8 - Nov 9
Bliss in Batavia near the Fox River
Smart TV, books
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
9.4 out of 10, Exceptional, (32)
"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. "
United States
Sarah J.
The price is ￥15,217
￥42,897 total
includes taxes & fees
Nov 3 - Nov 4
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
Property grounds
Friends-Inspired 3 BDR Escape Vintage Vibes & Private Garden Near Chicago
Friends-Inspired 3 BDR Escape Vintage Vibes & Private Garden Near Chicago
10.0 out of 10, Exceptional, (11)
"This was a great place to hang out with friends and our family. A nice selection of sleeping space, a big table to eat or play games together inside, and a well equipped kitchen.We especially enjoyed the backyard- pictures and descriptions are accurate. With the pool, grill, and multiple seating options, it was a great place to have some fun and hang out and visit. We highly recommend staying here!"
United States
Brenda R.
Friends-Inspired 3 BDR Escape Vintage Vibes & Private Garden Near Chicago
1 bedroom, desk, iron/ironing board, free WiFi
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
9.4 out of 10, Exceptional, (23)
"Nice little apartment. We enjoyed our stay. We even enjoyed the setting area outside."
United States
Jerilynn L.
The price is ￥15,065
￥41,124 total
includes taxes & fees
Nov 4 - Nov 5
Close to 3rd St & Train to Chicago/ Pets w fee /WIFI/W&D/Park Free/PrivateEntry
1 bedroom, iron/ironing board, travel crib, WiFi
Sunny 1BR Apartment in the Surburbs
Sunny 1BR Apartment in the Surburbs
5.4 out of 10, (3)
"Clean, quiet neighborhood. Apartment as pictured."
United States
Terri A.
The price is ￥12,478
￥28,524 total
includes taxes & fees
Nov 9 - Nov 10
Sunny 1BR Apartment in the Surburbs
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

Wyndham Garden Schaumburg Chicago Northwest

Wyndham Garden Schaumburg Chicago Northwest

10/10 Excellent
"Great "
Terrance 2-night trip
Posted 2 days ago
Wyndham Garden Schaumburg Chicago Northwest

Find out more about Sleepy Hollow

Search for holiday rentals in Sleepy Hollow on Expedia! You can easily find your home rentals, villas, holiday apartments in Sleepy Hollow using one of the methods below:

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Frequently asked questions

Are there vacation rentals in Sleepy Hollow?

Yes, we offer vacation rentals near popular local attractions in Sleepy Hollow, or you can go with a secluded option if you want a relaxing place to stay. Sleepy Hollow is known for its bars.

What's the top vacation rental that Sleepy Hollow has to offer?

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub: This vacation home rental outside of Sleepy Hollow is located in a rural location and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 larger area, you’ll find Randall Oaks Golf Club and Hemmens Cultural Center.

What’s a vacation rental in Sleepy Hollow like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Sleepy Hollow. Vacation rentals offer extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for small groups.