Holiday rentals in Sleepy Hollow

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Top-rated holiday rentals in Sleepy Hollow

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Loft in West Dundee

4.97 out of 5 average rating, 437 reviews

Hip Urban Loft - Small Town Charm -124 LOFTS #2

Luxury one-bedroom loft in the heart of downtown Dundee. Newly renovated 125-year-old building with timber ceilings, exposed brick walls and beautifully restored hardwood floors. Tastefully decorated and features a king-size Beautyrest mattress, luxury bed linen, private bathroom, kitchenette with under counter refrigerator, Kuerig coffee maker and lightning fast Wi-Fi for streaming your favorite shows on the 60” LED smart TV. 124 LOFTS offers 4 separate luxury lofts. Loft 2 is our most spacious

13–20 Oct

$198 SGD per night
Guest favourite

Guest suite in Bartlett

4.96 out of 5 average rating, 184 reviews

Cozy & Spacious Suite in Quiet Neighborhood

This 950 sq. ft. guest suite is in a quiet, upscale neighborhood, less than 1/2 mile from Bartlett Hills Golf Club and a mile from Metra Train Station. 50 min. train ride to downtown Chicago. 10 min. walk to downtown Bartlett. A private entrance makes check-in easy and convenient, while offering privacy during your stay. Full kitchen, accessible bathroom, WIFI, and cable provided. Washer/Dryer available upon request. Pool is for registered guests only. Owners on site to assist if needed.

27 Nov – 4 Dec

$147 SGD per night
Guest favourite

Guest suite in St. Charles

5.0 out of 5 average rating, 248 reviews

Peaceful Private Coach-House in St. Charles

Enjoy our cozy and peaceful Coach-house , private entrance with everything you need for a wonderful stay. Newly renovated and updated throughout. Queen bed, studio area includes blue ray player, reverse osmosis drinking water, Keurig coffee machine and quick-set lock. Even though you are less than a mile from downtown St. Charles and 4 miles to the Geneva train station you have a private area. You may see deer out your window overlooking the pool and tennis. Not suitable for children or pets.

28 Aug – 4 Sep

$125 SGD per night

Popular amenities for Sleepy Hollow holiday rentals

Stay near Sleepy Hollow's top sights

Spring Hill Mall3 locals recommend
Burnt Toast Restaurant4 locals recommend
Sushi Station3 locals recommend
Jimmy's Charhouse3 locals recommend
Village Pizza and Pub4 locals recommend
Rookies Sports Bar & Grill (Elgin)3 locals recommend

Other great holiday rentals in Sleepy Hollow

Guest favourite

Farm stay in Cherry Valley

4.97 out of 5 average rating, 266 reviews

Bed and Breakfast with Horse Hotel at VRR

22–29 Aug

$133 SGD per night
Guest favourite

Flat in Cary

5.0 out of 5 average rating, 154 reviews

A Peaceful Get-Away

25 Oct – 1 Nov

$171 SGD per night
Guest favourite

Home in South Elgin

4.89 out of 5 average rating, 118 reviews

River Front 3 bed 2 bath! Custom luxury getaway!

8–15 Feb

$225 SGD per night
Guest favourite

Guest house in Batavia

4.91 out of 5 average rating, 250 reviews

Quaint Batavia Coach House

19–26 Mar

$113 SGD per night
Guest favourite

Farm stay in St. Charles

4.96 out of 5 average rating, 182 reviews

Koi Sanctuary & Japanese Gardens Nature Ryokan Spa

30 May – 6 Jun

$414 SGD per night
Superhost

Flat in Crystal Lake

4.79 out of 5 average rating, 141 reviews

Downtown Living - Minutes to Restaurants!

6–13 Sep

$224 SGD per night
Guest favourite

Flat in Elgin

5.0 out of 5 average rating, 30 reviews

Peaceful Elgin APT King Bed

3–10 Sep

$175 SGD per night
Superhost

Serviced apartment in Algonquin

4.87 out of 5 average rating, 15 reviews

Waterfront 2 Room Studio w/Kitchenette, Downtown

14–21 Jun

$112 SGD per night
Guest favourite

Guest house in Hampshire

4.94 out of 5 average rating, 33 reviews

Shiloh Place - Two Minutes Off The Highway

7–14 Sep

$119 SGD per night
Guest favourite

Flat in Elgin

4.84 out of 5 average rating, 51 reviews

Cozy 1B/1B, luxe bed, parking spot walk to train

2–9 Nov

$167 SGD per night
Guest favourite

Guest house in Elgin

5.0 out of 5 average rating, 35 reviews

Carriage House

8–15 Jul

$210 SGD per night
Guest favourite

Guest suite in Hoffman Estates

4.98 out of 5 average rating, 65 reviews

One Bedroom - Suite

12–19 Aug

$154 SGD per night

Destinations to explore

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  3. Illinois
  4. Kane County
  5. Sleepy Hollow