Holiday rentals in Sleepy Hollow

Peaceful Elgin APT King Bed

Located in a sleepy suburban neighborhood, this freshly renovated apartment offers everything for a weekend getaway, business trip, or extended stay with a full kitchen, open living space & bedroom. Enjoy peace & nature while still being minutes away from restaurants, shopping, outdoor activities & all the Chicago suburbs have to offer. The Tipi BNB is a walkout lower-level basement APT that provides guests with the privacy and accessibility of a separate entrance and self check in/check out

Charming Riverfront Stay | Heart of Downtown

Welcome to The Riverfronts! Three boutique hotel rooms perfectly situated along the river in downtown West Dundee, offering scenic views and modern comforts. ✔ Riverfront Location: Enjoy the scenic riverwalk just steps away. ✔ Prime Downtown Spot: In the heart of downtown Dundee, minutes from top attractions and dining. ✔ Exclusive Group Booking: Reserve just one or all three units for your entire party. ✔ Outdoor Firepit: Unwind by the firepit, perfect for evening gatherings. ✔ Sleeps 4: Each

Master qtr close to nature & easy urban facilities

This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

Penthouse In The Historic Hobbs

Experience luxury and historic charm at the Penthouse in the Historic Hobbs. Built in 1892, and restored in 2023, this new one bedroom corner unit offers a panoramic view of the Aurora skyline. Cook a delicious meal in the fully stocked kitchen. Dine at the bespoke table in the window bay under the iconic onion dome. Relax on the cozy sofa and enjoy a movie on the big screen TV. Rest in the plush king-sized bed. This urban retreat is near coffee, shopping, art and entertainment.

Waterfront Stay w/ Walk to Downtown Entertainment

Apartment overlooking the Fox River. Walking distance to downtown Algonquin. Free wifi & cable TV. Don't impose on family or friends, or settle for the bland experience of a box hotel. Instead, book a comfortable stay with great amenities and enjoy the river and downtown entertainment. You'll be able to relax, get a restful sleep, and enjoy your visit. You'll also notice the little touches and the extra effort made to assure you have an awesome stay. Private Bathroom and Kitchen.

Cozy Lakefront! Hot Tub-Fishing-Kayak &Pool Table

Very large guest suite w/3 separate areas. Just like your own apartment. Great for friends traveling together! ENTRANCE IS THRU THE MAIN PART OF THE HOUSE. This is just for the basement but you have complete privacy down there. Fenced-in yard, hot tub, large patio, bbq, firepit, enjoy fishing or sitting watching the beautiful sunsets. Stocked lake, walking path, 3 parks! Check out the pictures to see all our home has to offer! Full kitchen,laundry room & yard are shared space

Cozy, Comfy, Close to Downtown

Discover serenity in our centrally located guest apartment in our charming St. Charles cottage. The space is pet-friendly with a fenced yard, featuring a spacious kitchen, living room, bath, queen-sized bed, and in-unit laundry. The yard offers views of the Fox River, a peaceful patio, with award-winning parks & biking trails at your doorstep. Note: The unit is studio style located in the lower level of a home. The space is completely private. Only outdoor spaces shared. 😊🪻🏡

124 Lofts - Downtown Dundee - Walk to Dining

124 Lofts is a boutique collection of modern, design-forward lofts set within a beautifully restored historic building in downtown West Dundee. This listing is for Loft #4, a one-bedroom space featuring exposed brick, warm textures, and a comfortable layout that blends industrial character with a relaxed, inviting feel. Each loft includes a king bed, private bath, kitchenette, fast Wi-Fi, and a 60" smart TV, just steps from restaurants, shops, and the Fox River.

Sherwood House

Enjoy the ambience of the Sherwood House, an 1884 Victorian built for Judge David Sherwood. Use of entire first floor apartment including a full kitchen is perfect for longer term stays. Original features include multiple stained glass windows, beautiful wood work, multiple decorative fireplaces and hardwood floors. Located just blocks from downtown Elgin, walk to shops, restaurants, the casino, bike trail or Metra. WiFi and off street parking.

“The remote retreat”

We have a cozy one bedroom apartment that is available on the top floor of the home and has its own independent and separate entrance! Comes with free parking on premises; recently renovated; neighborhood is safe and quiet. Shopping center with grocery store, laundry mat and restaurant is available within walking distance! We are only 5 minutes from the expressway I-88 and 10 minutes from Naperville and the outlet mall in Aurora!

Little Fox Cottage - A Cozy Riverview Getaway

A cozy getaway in the Northwest Suburbs of Chicago. Located 40 miles from the city and just 1.25 miles from the Fox River Grove Metra stop. Get away from the city or 'work from home' in our 1 bedroom cottage with a giant covered outdoor space tucked against the slope of a beautifully terraced hill.

Carriage House

This unique place has a style all its own. Completely renovated 1900 Carriage house . Originally a saloon and dance hall . Totally fenced and great play area for children and pets. The Little Blue House is on same property . It sleeps four and is also available for rent .