
Holiday rentals in Shorewood
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Top-rated holiday rentals in Shorewood
Guests agree: these stays are highly rated for location, cleanliness and more.

*The Belltower Haven*Large*Family Friendly*Wi-Fi
Our remodeled spacious apartment is located on Plainfield Road, minutes away from 1-80 & 1-55. Near: Rialto Theatre, Haley Mansion, Jacob Henry Mansion, Train Station, College of St. Francis, Joliet Junior College, Slammers Minor League Baseball and St. Joe's Hospital, New Lenox Sports Complex Minutes away from: Chicagoland Speedway, Hollywood Casino, Lewis University and Silver Cross Hospital. 30 minutes from Chicago 3 br (3 Queens beds 1 queen sleeper sofa, queen air mattress), 1 full bath

The Garden House - Murals and more
Our garden-themed house🌿 located on busy Plainfield Road is minutes away from 1-80 & 1-55. Near: Rialto Theatre, Haley Mansion, Jacob Henry Mansion, Joliet Union Station, College of St. Francis, Joliet Junior College, Slammers Minor League Baseball & St.Joe's Hospital. Minutes from: Chicagoland Speedway, Hollywood Casino, Lewis University & Silver Cross Hospital. 30 miles SW of Chicago. 🏡Entire house: 2 Bdr (2 Bd & 1 Futon), Bathroom (new shower), Living Room, Kitchen, Front Deck

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.

Historic Pioneer House
Relive the early days of Plainfield by staying at the historic Pioneer House! Charming cottage built in 1834 has tons of character. 2 bedrooms, 1 bath, kitchen, living room, dining room, laundry facilities, and outdoor living. Parking off street for 2 cars. Mature landscaping with outdoor seating. Walking distance to downtown Plainfield, loaded with coffee shops, boutiques and restaurants. Stay in a quiet, safe neighborhood with easy access to all that Chicago has to offer.

*Charming Canal-Port Cottage* ~ No Cleaning fees~
Escape to our **Cozy Canal Port Cottage**, where nature meets relaxation. Nestled on the historic I&M Canal and minutes from downtown Morris, this charming 2-bedroom retreat offers peace, comfort, and wildlife views. Enjoy a fully equipped kitchen, grilling area, comfy beds, and a serene setting near Starved Rock and Buffalo Rock. Perfect for couples or small families to unwind, explore, and recharge. We can not wait for you to stay with us.

“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!

Spacious 4BR, 2 Living Rooms Family & Pet Friendly
😴 A calm, spacious retreat where families truly sleep well. 🛏️ 4 private bedrooms (2 King, 2 Queen) with extra-comfy, plush furniture. ✨ Spotless & pristine, top to bottom. 🛋️ 2 living areas—room for grandparents to relax while kids play. 🌳 Peaceful, tree-lined street, just 45 min to Chicago. 🐾 Pet-friendly w/ private yard. 🔑 Effortless self check-in. 🚗 Free parking. Your restful home base awaits!

Cozy Lakeview Studio with Private Access
Enjoy luxury and comfort in this cozy lakefront studio with a private entrance, attached to a home where the friendly hosts reside. The studio offers a plush queen bed, a kitchenette with a mini fridge, microwave, induction cooktop, and a full bathroom. Located in one of Naperville’s safest neighborhoods, it’s just moments from cafes, restaurants, markets, and a biking trail, with easy access to I-88.

Lockports Famous Hideaway ~ 2bdrm Guest House Flat
A history buff’s dream filled with antiques & artifacts relating to Chicago, Joliet, Lockport, the I & M Canal & "Route 66"! Family & Business Friendly. The entire upstairs 1,500 sq ft vintage 2-bedroom house apartment is all your own space. The flat is NOT shared with other guests/host. Private-entrance/self-check-in. Have a 'historic' stay at the "Hideaway"! Can accommodate up to 6 guests.

Modern Comfort, Ideal for Business or Family Trips
Relax in this stylish, spacious, and peaceful home, perfect for families, small groups, or extended stays. Enjoy bright living areas, a fully equipped kitchen, and clean modern bathrooms. Conveniently located near shopping, dining, and parks, this calm, welcoming home is designed for comfort, privacy, and a stress-free stay.

Comfy 1-bedroom apartment in Joliet
This cozy apartment in the Cathedral Area of Joliet offers modern amenities like a walk-in shower, king-size bed, and fiber internet. You'll also appreciate the historic neighborhood and gorgeous sunsets from the front stoop.

Engler’s Escape- Catfish cabin
Take a break and unwind at this peaceful oasis. Enjoy the natural beauty and sounds that surround this little getaway. Relax riverside and recharge.
Popular amenities for Shorewood holiday rentals
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Destinations to explore
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- Wrigley Field
- Soldier Field
- United Center
- Lincoln Park
- Grant Park
- Navy Pier
- Millennium Park
- 875 North Michigan Avenue
- The Field Museum
- University of Chicago
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Matthiessen State Park
- Donald E Stephens Convention Center
- Union Park
- Garfield Park Conservatory
- Byline Bank Aragon Ballroom
- Oak Street Beach
- University of Illinois At Chicago
- Northwestern University
- Chicago Theatre





