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Charming Ranch-Style Cottage

Escape the hustle and bustle of the city in this relaxing, cozy, cottage that is a few blocks away from downtown Highland Park and Highwood, with great restaurants, bars and coffee shops. It is perfect for single travelers, couples, or a small family. We are grateful for the amazing Airbnb hosts across the globe, who opened their homes to us, and made our trips so memorable. So when we bought our own home, it was only right that we would return the favor and open our home to fellow adventurers

Sanctuary on the Ravine

Take it easy at this unique and tranquil get away, walking distance to Ravinia and Beaches 3 Blocks.This historic, beautifully decorated and well maintained home has a lovely, peaceful & serene setting. Multiple indoor and outdoor seating arrangements. Fully stocked kitchen that opens to family room looking out onto several multilevel brick patios and a quiet, private ravine. The extra large living room has a down feathered sectional couch that seats up to 10 people. No parties or gatherings

Chic Studio in Downtown Highland Park near Metra

Welcome to downtown Highland Park! Experience comfort and convenience in our cozy studio apartment with FREE parking. Just a 5-minute walk to the Metra, and within a leisurely 15-minute stroll, enjoy breathtaking views of Lake Michigan. Explore historic Fort Sheridan Forest Preserve and beach, only a quick 5-minute drive away. Discover delightful dining, gelato shops, parks, and more—all within walking distance. Our well-appointed apartment ensures a memorable stay in this vibrant neighborhood.

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.

Mr. Hughes’ Attic, an 80s-themed coach house

Welcome to Mr. Hughes' Attic, a private coach house that pays homage to John Hughes (who filmed many of his movies nearby!) Located in NW Evanston, your stay includes a queen bed, full kitchen, laundry, full bath, dedicated workspace, private balcony, free parking, streaming TV, and more. We're a short walk to Central St shops, restaurants, and the Metra train, a five-minute drive to Northwestern, and less than 30 minutes to Chicago. Not wheelchair or ADA accessible. License# STR004.

Spacious Garden Apartment with Sauna and Fireplace

English garden apartment in historic Wilmette home with a private entrance, sauna, washer/dryer, kitchenette, dining area, recreation room with pool table, vintage pinball machine, and a wood-burning fireplace with gas igniter. Two queen beds, 1 full-size sleeper sofa, and a single mattress are available for large families. Ideal access to Northwestern University for all events. **Please note the apartment is located on the garden level and does NOT include the entire home.**

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.

BRAND NEW*Sleeps 7*Near Navy Base*3 BDR*3 Smart TV

Modern 3-bed, 4-bath home in Highland Park, IL, steps from Ravinia Festival. Recently renovated with an open-concept living area, gourmet kitchen, and stylish, comfortable bedrooms. Ideal for families, with easy access to downtown shops, cafes, and parks. Perfect for relaxing after concerts or exploring local charm. Book your stay for a memorable experience!