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.
Loft in West Dundee
4.97 out of 5 average rating, 437 reviewsHip 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
Guest suite in Bartlett
4.96 out of 5 average rating, 184 reviewsCozy & 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
Guest suite in St. Charles
5.0 out of 5 average rating, 248 reviewsPeaceful 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
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Sleepy Hollow holiday rentals
Other great holiday rentals in Sleepy Hollow
Farm stay in Cherry Valley
4.97 out of 5 average rating, 266 reviewsBed and Breakfast with Horse Hotel at VRR
22–29 Aug
Flat in Cary
5.0 out of 5 average rating, 154 reviewsA Peaceful Get-Away
25 Oct – 1 Nov
Home in South Elgin
4.89 out of 5 average rating, 118 reviewsRiver Front 3 bed 2 bath! Custom luxury getaway!
8–15 Feb
Guest house in Batavia
4.91 out of 5 average rating, 250 reviewsQuaint Batavia Coach House
19–26 Mar
Farm stay in St. Charles
4.96 out of 5 average rating, 182 reviewsKoi Sanctuary & Japanese Gardens Nature Ryokan Spa
30 May – 6 Jun
Flat in Crystal Lake
4.79 out of 5 average rating, 141 reviewsDowntown Living - Minutes to Restaurants!
6–13 Sep
Flat in Elgin
5.0 out of 5 average rating, 30 reviewsPeaceful Elgin APT King Bed
3–10 Sep
Serviced apartment in Algonquin
4.87 out of 5 average rating, 15 reviewsWaterfront 2 Room Studio w/Kitchenette, Downtown
14–21 Jun
Guest house in Hampshire
4.94 out of 5 average rating, 33 reviewsShiloh Place - Two Minutes Off The Highway
7–14 Sep
Flat in Elgin
4.84 out of 5 average rating, 51 reviewsCozy 1B/1B, luxe bed, parking spot walk to train
2–9 Nov
Guest house in Elgin
5.0 out of 5 average rating, 35 reviewsCarriage House
8–15 Jul
Guest suite in Hoffman Estates
4.98 out of 5 average rating, 65 reviewsOne Bedroom - Suite
12–19 Aug
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