Vacation rentals in Ravinia

*King bed *Outdoor Living *Sought-After Area

Welcome to our sophisticated ranch style home, nestled in the serene, central Chicago neighborhood of Northbrook. This carefully curated home offers a peaceful retreat in a walkable neighborhood with nearby shopping and dining. With its elegant decor, comfortable furnishings, and modern amenities, the home provides a haven of relaxation. Whether you're enjoying a cup of coffee on the private patio or exploring the area, this home provides the perfect backdrop for a memorable vacation experience.

Best Deal in Chicago | Great Food & Free Parking

Clean & modern Avondale apt close to Blue Line, perfect for urban explorers! Stylish decor, comfy bed, and a cozy ambiance await. Explore nearby cafes, bars, and boutiques, or hop on the train for downtown adventures. Easy to access & great neighborhood. Easy permit parking (free passes provided) on street allows for the ability to drive or take public transportation wherever you want to explore. Avondale has been voted one of the best neighborhoods in Chicago! Come see what the fuss is about.

Month-to-Month Studio Sleep Sanctuary-w/ Peloton

Perfect location! Quiet side-street location, 2 block to Metra. Charming apartment with designer touches overlooking a park and a 10-minute walk to Rosewood Beach on Lake Michigan. Our centrally-located studio apartment has everything you need to call it home—full size kitchen amenities, small appliances, and full bathroom with lots of hot water, very quiet. No neighbors above or below. Very cozzzy! Free lot parking (must provide license plate), free shared laundry, and Walgreens steps away

Lovely studio near the beach! (and heated floors!)

Get away from the city to this studio in Highland Park. The newly renovated space has everything you need for a relaxing getaway—huge comfy couch, brand new bed with Brooklinen + Parachute bedding, pristine bathroom, and lots of amenities. Downtown Highland Park, Highwood, + the beach are just a walk away. There's access to grocery stores, restaurants, and shops, and you can retreat to the quiet of your studio when you're ready to unwind. Ps. For the winter months: We've got heated floors.

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.

Full Apartment green oasis in law suite

Beautiful & spacious 1 bedroom, 1 bath in law apartment. New windows with green views. Fragrance free home. There are Curtains in the living room & kitchen. Designated Parking onsite. Full kitchen full sized stainless appliances, private stackable washer and dryer machines & beautiful tile throughout. Bring slippers tile can be chilly to touch - if barefoot. Starbucks, parks, restaurants, dry cleaners & Jewel walking distance from apartment. Whole Foods & Target 7 min. drive. NO PARTIES.

Chic Downtown Studio Near Ravinia w/ Free Parking

Discover urban comfort in the heart of Highland Park, IL. Stay in our fully renovated studio apartment, perfectly located just steps from the Metra station, local cafés, and vibrant downtown attractions. Enjoy a sleek, light-filled interior with large windows and skylights that create an airy, modern feel. You’ll be minutes from Lake Michigan’s beautiful beaches, Ravinia Festival, and boutique shopping. Experience refined comfort and convenience—your Highland Park getaway starts here!

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Charming in-law suite w/ use of deck and yard

Charming home in Highland Park. The space is my in-law suite which is in the lower level of my home and has its own full size kitchen and bathroom. We live up-stairs with our 3 little dogs so we will be available if you need anything during your stay. The in-law suite is set up like a studio and has one queen bed,a separate closet area and laundry. Please note- the suite is in the basement, but there is natural light. You have shared use of the deck/yard if desired.

A Wonderful Getaway Home on the North Shore!

A perfect place to visit the northern highlights of Chicago! 1/4 mile from Ravinia! 1.5 miles from the Botanic Gardens! 30 minutes from Chicago (an hour and a half from Milwaukee). Close to trains, planes, and easy automobile access. A two-bedroom gem in the heart of so many wonderful things. Other local places include Northwestern University, Lake Forest, Winnetka, and Lake County. I have a cat living here, but he will accompany me when I leave.

Spacious*Near Navy Base & Botanic Garden*7 Guests

Modern 3-bedroom, 4-bath home in Highland Park, just steps from Ravinia Festival and the Botanical Garden. Only 20 minutes to the Navy base and a quick train to downtown Chicago. Features an open-concept living area, fully equipped kitchen, and cozy bedrooms. Perfect for families, military visitors, or concert lovers. Unwind after a day exploring or at a show—comfort and convenience await. Discover the best of Highland Park. Book your stay today!

Cozy 2-Bedroom Cottage Near Downtown Highland Park

Step into comfort and character in this beautifully updated home’s front suite. Featuring two comfortable bedrooms, a private bathroom, and cozy living spaces decorated in modern farmhouse style. Enjoy a well equipped kitchenette, free coffee & tea, and a prime Highland Park location. Walk to shops, restaurants, parks, and easy access to Chicago.