
Holiday rentals in Lakewood Shores
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Top-rated holiday rentals in Lakewood Shores
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Starved Rock Retreat w/hot tub & full-fenced yard!
2-bedroom, 1-bathroom pet-friendly townhouse with fenced yard in a quiet neighborhood close to everything. Ideal for couples, yet comfortable for all travelers. Safe, private, and well-suited for remote work. Enjoy an open floor plan and a new patio with a year-round hot tub & seating area. Fully fenced yard with a 6-ft vinyl privacy fence is exclusively yours. No pet restrictions. Includes in-unit laundry and two bedrooms - one set up as an office/workout space. Peaceful and made for unwinding.

Get Your Kicks in Our Cozy Cottage Near Route 66
Enjoy the comforts of home when you have to be away. Our fully furnished cottage is located 4 miles from Rt 53 / Historic Rt 66 & just blocks from the Kankakee River. Just 5 minutes to "downtown" Wilmington featuring restaurants, a wine bar, a local brewery, and multiple antique stores. ✧ Easy access to everything that Joliet has to offer just 20 miles away, including the Autobahn and Route 66 Raceway / Chicagoland Speedway. ✧ 7 miles to easily access I55 for a quick ride into Chicago.

Lyle and Taylor present-Slice of Home on the Road
Your "HOME FEEL" on the road. Beautiful, private 2 Bedroom, 1 Bath apartment. Free Wi-Fi. Cable TV with 144 channels plus HBO, SHOWTIME, Cinemax. Ample Living room seating w/50" SmartTv Netflix ready (with your account). Desk office area, King Bedroom w/TV, Queen Bedroom, and Sofa for 5th guest. Washer & Dryer incl Laundry supplies. Hair dryer, Keurig coffee maker, Kcups, flavored creamers, tea, hot chocolate. Full kitchen, microwave, toaster, blender, essential spices. Iron & ironing board.

Country Home with Outdoor Hot Tub by Starved Rock
Beautiful Country Home with private outdoor Jacuzzi Hot Tub secluded by farmland on almost 3 Acres in North Utica Huge outdoor fire pit and concrete patio too Lots of parking space enough for a boat and trailer Starved Rock, Buffalo Rock, Matthiessen State Parks and the Illinois river are close by for hiking ,fishing or kayaking Starved Rock Marina and Sky dive Chicago are close by Dining and Shopping only a few miles away in downtown Utica Ottawa or Peru A unique and tranquil getaway.

Quiet Farmhouse Retreat
Looking for a tranquil farmhouse destination? Get away at Wadsworth Acres- a Scottish Highland hobby farm! This modern farmhouse is the perfect space to relax. Complete with a very spacious primary suite, large eat-in kitchen, exercise room, and space to play outside- you’ll never have to leave! Enjoy your morning coffee with breathtaking farm sunrises on the patio and evenings in the hammocks.Peaceful escape just 5 minutes from the highway, 10 from historical downtown, 35 from the Dunes!

Tranquil Haven, 1 King Bed, Retreat by the River
Welcome to ✤Tranquil Haven✤ Your cozy, boho inspired retreat and home away from home! This spacious and modern upstairs apartment is the perfect place for couples, medical professionals, and business travelers. ✤Tranquil Haven✤ is centrally located and close to popular restaurants, shops and fun attractions. ✶ 1.7 Miles to Olivet Nazarene University ✶ 1.3 Miles to Riverside Medical Center ✶ 1.2 Miles to Perry Farm Park ✶ 4.9 Miles to Kankakee River State Park ✶ 55 Miles to Midway Airport

Chic Retreat Small Town Charm, City Sophistication
The ultimate escape, at Wells on Main Guesthouse & Gatherings where small-town charm meets big-city sophistication. Whether it’s a romantic getaway, girls’ weekend, or just time to recharge, our elegant retreat has you covered. Couples can cozy up in dreamy spaces and create lasting memories. Gather your best friends for laughter, wine, and chic relaxation in a stylish setting. With local charm and upscale comfort, every moment feels magical. Book a week long stay and receive 40% off ❤️

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"! *Note: Pricing is based on "Double Occupancy". Can accommodate up to 6 guests. Extra charges per person apply after 2 guests.

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.

Cheerful 2 bedroom home near Rt. 66
Soak up the hometown charm with a relaxing and tranquil stay in historic Wilmington near the Kankakee River. You won't be living in a van down on the river during this stay. You'll enjoy a warm, cozy home that's near shopping, flavorful restaurants and picturesque sunsets on the Kankakee River. This two bedroom home can accommodate up to six people. The kitchen and living room feature an open concept for more intimate or a night with close friends.

Updated, bright, and modern, 3 bedroom home.
You will be comfortable in this newly remodeled three bedroom, two bathroom home. ✶ 6.7Miles to Olivet Nazarene University ✶ 8.4Miles to Riverside Medical ✶ 11Miles to Kankakee River State Park ✶ 43Miles to Midway Airport The home FEATURES: *Safe, quiet, walkable neighborhood *3 Bedroom; 1 King, 1 Queen, 2 twin beds *Spacious fully equipped kitchen with coffee station *Washing Machine, Dryer & Dishwasher * Fast Wi-Fi

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.
Popular amenities for Lakewood Shores holiday rentals
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Destinations to explore
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- Millennium Park
- United Center
- Grant Park
- Chicago River Walk
- Soldier Field
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Union Park
- University of Chicago
- Matthiessen State Park
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Willis Tower
- The 606
- Chicago Cultural Center
- Auditorium Theatre
- Chicago Theatre
- DuSable Black History Museum and Education Center
- Northerly Island
- Chicago Riverwalk
- Adler Planetarium





