Vacation rentals in Sleepy Hollow

Townhouse in Hoffman Estates

4.97 out of 5 average rating, 34 reviews

Game Room | Exercise Area | Firepit | Sanitized

Make yourself at home in this cozy, private townhouse, perfect for families and groups! Conveniently located 20 min from O’Hare, 40 min to downtown Chicago, and near NOW Arena, Schaumburg Convention Center, Woodfield Mall and St. Alexius Hospital. Sanitized after each guest, it features a full kitchen, family games, foosball table, walking pad, Smart TVs, fireplace, laundry room, and a yard with a firepit. With extra futons in the basement, there’s plenty of space. Message me with any questions!

4.99 out of 5 average rating, 76 reviews

Apartment in Elgin

Peaceful Elgin APT King Bed

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

4.96 out of 5 average rating, 369 reviews

Loft in West Dundee

Hip Urban Loft-Small Town Charm - 124 LOFTS #1

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. Book one Loft or all four.

4.96 out of 5 average rating, 74 reviews

Apartment in West Dundee

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

Guest suite in Carpentersville

4.93 out of 5 average rating, 14 reviews

Cozy Countryside Cottage with private patio

Escape to our charming cottage, the perfect retreat for a relaxing countryside getaway in DUNDEE. This hideaway is designed for travellers seeking tranquility, featuring all comforts of home. Immerse yourself in nature and enjoy the peaceful atmosphere from your PRIVATE PATIO. Discover charming shops and restaurants in downtown Dundee and Algonquin offering local cuisine and unique finds. Enjoy outdoor activities at the nearby Fox River Trail. This house is ideal for unwinding and recharging.

4.96 out of 5 average rating, 213 reviews

Guest suite in Bartlett

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.

4.99 out of 5 average rating, 659 reviews

Guest suite in Geneva

A Suite within a Cozy cottage in Geneva Illinois.

Cozy private suite in the lower level. Guests have the suite to themselves. The bathroom is adjacent to the room and is private. There is a small fridge, a coffee maker, and a microwave oven. We are in Geneva, Illinois. We are LGBTQ+friendly. Our space is ideal for shorter stays and visitors on the go . Not suitable for staycations. Quiet area. Hosts live on the upper level and guests pass through our space to get to the suite. In a bind we can accommodate a 3rd guest and a pet. Welcome.

4.82 out of 5 average rating, 49 reviews

Apartment in East Dundee

Charming Historic 2BR/1BA Getaway #2 in E. Dundee

You can't beat the location of this charming 4-flat that used to be a school house. 2BR/1BA, hardwood flooring throughout. Has all the charm you would expect East Dundee to offer. Literally steps away from everything Downtown East Dundee Has to offer. Great new bakery, to grab breakfast in the morning, right around the corner. The bike path is just a block away. Rockhaus, just 3 blocks. No need to even pay for an uber. Ask me about our 2nd unit right next door. I can send the link

4.79 out of 5 average rating, 121 reviews

Apartment in Algonquin

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. (be sure to see our guidebook!) 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.

4.79 out of 5 average rating, 169 reviews

Apartment in Elgin

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.

4.94 out of 5 average rating, 31 reviews

Townhouse in Elgin

Fully Renovated and Updated Home

Escape to this inviting 3-bedroom townhome, your perfect Elgin retreat. Unwind in style with two plush queen beds and a comfortable full bed, ensuring restful nights. Two modern bathrooms offer convenience and privacy. Electric vehicle owners will appreciate the dedicated charger. Explore the vibrant city of Chicago, just a 45-minute drive away. With Route 90 just 5 minutes away, you're well-connected to explore the area.

5 out of 5 average rating, 6 reviews

Home in Crystal Lake

In Ground Pool, Full Ranch Home

In ground pool!! Rent this entire home, experienced hosts, near town, 5 min drive to Crystal Lake main beach OR Three Oaks Beach/Recreation. Clean, Updated Home, with fenced in yard and pet friendly. 4 beds total (3 bedrooms) and 1 full bath. Fully stocked kitchen with all cooking supplies that you need. Basketball hoop in driveway, bags set in yard, great summertime home! Walk to Marianos/CVS/Walgreens, near it all!

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Other great vacation rentals in Sleepy Hollow

5 out of 5 average rating, 40 reviews

Private room in Elgin

Ashiana #3 Private Bedroom Private Bathroom

SamanthaRating, 5 stars2 months ago

I felt drawn to this listing the moment I set eyes on it. Nazneen & Mehtab went above & beyond as hosts. From staying up late to welcome me into their home even after my schedule was delayed, to sparking engaging conversations over breakfast in the morning, to inviting me to sit in on their family’s Zoom wedding—their hospitality & flexibility is unmatched. I thoroughly enjoyed staying here and won’t hesitate to do so again the next time I’m in Elgin. Nikah Mubarak to Areeb & Zoha!

Private room in Mount Prospect

4.89 out of 5 average rating, 114 reviews

S2 Private studio in the house. 15min to O'Hare

MitchRating, 5 stars2 weeks ago

Enjoyed our short stay near ORD. Lots of options nearby as well, such as a park, CVS, and restaurants. Room was spacious, clean and comfortable. Thanks!

4.93 out of 5 average rating, 165 reviews

Private room in Cary

Casa de Cary 1 (private driveway/entrance/wifi)

BrianRating, 5 stars4 months ago

What a wonderful place to stay. Everything was fantastic, the bed the TV and cozy warm room. They went out of their way to make sure my entrance and driveway was snow free. would love to stay again soon.

Hotel room in Bloomingdale

4.8 out of 5 average rating, 86 reviews

Renovated Comfortable Room l NO Cleaning Fee

AyeshaRating, 5 stars2 weeks ago

We stayed for 2 nights and had a great experience. The place was clean, peaceful, and very comfortable—just what we were looking for. The host was very welcoming and proactive, which made the stay even better. It would be a nice touch to include a couple of water bottles and some hand wash, but overall everything was lovely. Highly recommend!

4.85 out of 5 average rating, 62 reviews

Private room in Bartlett

My House is Your House

EricRating, 5 stars3 weeks ago

Debbie was very nice and the place was very clean. Would stay there again.

Private room in West Chicago

4.89 out of 5 average rating, 62 reviews

Stay Long Term @ The Resting Place - Narragansett

LuckyRating, 5 stars2 weeks ago

Great place to stay -- Was greeted by a super friendly cat! Awesome walk in kitchen to use, nice room -- felt like in a hotel suite! Nice living space to relax and bathroom nearby if needed. Loved the additional code lock on the bedroom door for privacy! Overall great place, great hosts as well -- recommend checking out their local guidebook for Food as well. Highly Recommended.

Private room in Schaumburg

4.96 out of 5 average rating, 53 reviews

Stylish Room in the Chicagoland Area

GabeRating, 5 stars1 week ago

I enjoyed my stay at Ana's place, she's wonderful and respectful of one's privacy. The place was clean, organized and close to many businesses, parks and food places. Would love to stay here again. Thank you Ana!