Holiday rentals in Cook County

Evanston 2BR 2Bth 1 Blk to Beach

With its older charm, modern comforts, and unbeatable proximity to the beach, this 2-bedroom, 2-bath unit offers an ideal getaway. Only 1 block from beautiful Lake Michigan and South Blvd Beach, you will love our spacious, sunny apt. Whether you're staying for a short visit or a lengthy one, you'll feel the comfort of home on a tree-lined street. The unit has hardwood floors throughout, comfortable bedrooms, a fully stocked kitchen, dining room, and a sunroom looking out on the backyard patio.

1920s fully updated unique open artist loft space

True artist living loft space!!! One of a kind space in a safe area of the western suburbs close to the city and easy commute to shops stores. very close to trains buses and expressways. Private parking lot. No unit above or below. Quiet and private spacious updated wide open loft. Hardwood floors throughout forced heat and ac slated steel designer bathroom.. Double oven dishwasher electric cooktop sub zero fridge microwave and toaster oven. Ceiling fans two beds. Can sleep 6 for added cost

Enchanted Garden Treehouse (Amenity*)

Spring is here, the flowers out, the treehouse warm and cozy, and the hot tub ready! Relax on cool evenings in our luxurious, very private, 4' deep cedar hot tub nestled in the evergreens, while the moon and stars swirl overhead, the waterfall cuts thru snow into the koi pond, and the fire table and torches blaze. The running stream makes this a wildlife refuge, with tons of birds, squirrels, rabbits, foxes and hawks. We are 420 friendly. Come experience the magic and make a special memory!

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Located on a tranquil city side street, this property is walking distance to numerous restaurants and stores. Enjoy easy access to public transportation, including Metra train, CTA Pink Line, and a direct CTA bus to Midway Airport. Downtown Chicago is a mere 20-minute drive away, with the United Center and Soldier Field just 15 minutes away. Ideal for a quick getaway, an overnight stay before your flight, or an extended work assignment. Unwind on the patio, complete with a fire pit and grill.

RetroModern Bungalow | free parking | pet friendly

Experience the city in style at Retro Modern Bungalow, the perfect pad for up to four friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location—just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Cozy & Bright Townhome near O’hare -Self Check In-

Escape into this Montclare Masterpiece! Be one of the first guests to enjoy our revitalized, fully-stocked home with attached deck. This 3-level home comes with a spacious, light-flooded living area with attached open kitchen w/ SS appliances, granite countertops/ backsplash, and accent lighting - perfect for larger groups. On the third level you'll find 2 elegant bedrooms with ample closet space, updated full bathroom, and in unit washer and dryer provide all the essentials and more!

A guest suite centrally located, but so quiet

IF... you want to race into the city to see a play, go for a jog along the lake, have a quick coffee with a friend or enjoy a fine restaurant to celebrate a special occasion, it's all here in the lovely lakeside town of EVANSTON, IL. You can enjoy it all while living in my private guest suite w/kitchenette, private bath, private entry, shared laundry area and......., if you need it, garage parking, too! Enjoy my garden on warm summer days; in winter, you will love the heated floor!

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

Lovely top floor 2BR/2BA, steps from everything!

BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.

Games, Grounds, Goodness in DG

Our family loves games and when travelling it is great to have entertainment for the whole family. Our game room includes a video arcade game with over 400 options, boardgames and more! Maybe simple cards or puzzles are your preference--we have them all in this fully furnished home with large backyard to play in. Bedroom 1--bunk bed with full on bottom, twin on top Bedroom 2--queen bed with room for a play pen Stay for a weekend or longer and know fun will be had!

Cozy French Inspired Cottage in rural setting

Relax and escape to our charming, one of a kind cottage. Beautifully decorated with period furniture and tastefully updated with modern amenities. The cottage offers slate tile and hardwood floors. Original pine floors line the upstairs loft bedrooms. Cook in a French inspired country kitchen with butcher block counter tops. Rural setting, yet minutes away from everything! Downtown is a 20 min. walk and the Metra will take you to the city in 45 minutes!

Mid-Century Charm. Near Chicago. Low Cleaning Fee!

Step back in time a bit with our charming 2nd floor walk-up in a quiet, safe suburb. Parking included on-site. Vintage, welcoming vibe. We're a 20-30 minute drive to downtown Chicago (depending on traffic). The unit is on the 2nd Floor and is separate from the rest of the house (we live on the 1st floor). 1 Dedicated Guest Parking spot (included). Additional Free Parking is available. Great wifi. 3-season back porch. Record Player (Real Vinyl!)