Vacation rentals in Fort Sheridan

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Top-rated vacation rentals in Fort Sheridan

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Rental unit in Highland Park

Chic Studio in Downtown Highland Park - By Metra

Welcome to our elegant studio unit in Highland Park, now with FREE parking! Our simple yet comfortable space is ideal for couples, concert goers, and families of 2. Enjoy all of the basic amenities and creature comforts you need, including a stocked kitchen, laundry, and Wi-Fi. Our location is ideal for exploring downtown of Highland Park, with easy access to top attractions, restaurants, and shops. Book now and experience the perfect home away from home for your next trip to the North Shore.

$90 per night

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Private room in Highland Park

Private Dove Room in Charming Cottage

Escape the hustle and bustle of the city in this relaxing, cozy, ranch-style cottage that is just a few blocks away from downtown Highland Park and Highwood, with great restaurants, bars and coffee shops. It is perfect for single travelers, or couples. 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 got our own home, it was only right that we would return the favor and open our home to fellow adventurers

$77 per night

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Rental unit in Highland Park

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.

$153 per night