Holiday rentals in Cook County

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Top-rated holiday rentals in Cook County

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

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Guest favourite

Rental unit in Berwyn

4.91 out of 5 average rating, 309 reviews

Private apartment with retro vibe

Gunderson Getaway is a cosy one BR apartment with some retro style touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus sofa & extra single bed available. EASY free street parking right by unit. Quick drive to City. Convenient to both airports, United Center and walk to Fitzgerald’s Club. Near Blue Line, restaurants, groceries, great bakery. NO smoking, candles or glitter! Pets MUST be pre-approved and never left alone.

Guest favourite

Home in Berwyn

4.99 out of 5 average rating, 106 reviews

Retro Modern Bungalow w/ fire pit and free parking

Experience the city in style at Retro Modern Bungalow. The perfect crash pad for up to four friends and two pups. Featuring two spacious bedrooms, each w/ a king bed + luxury linens, a propane fire pit and a fully fenced backyard. Enjoy central HVAC, hi-speed 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.

Guest favourite

Rental unit in Forest Park

4.99 out of 5 average rating, 131 reviews

Sunny 1 bedroom apartment 1 block from restaurants

This sunny second floor apartment perched in an 1890’s farmhouse offers traditional charm with many contemporary touches. It showcases a variety of original art. Located on a quiet street but just steps away from restaurants, bars and shops, off-street parking is included. Two nearby trains provide easy access to downtown Chicago and O’Hare Airport. An enclosed porch directly off the kitchen overlooks a beautiful prairie garden. You can relax on the backyard patio with gas grill and fire pit.

Guest favourite

Rental unit in Chicago

4.96 out of 5 average rating, 140 reviews

Designer Avondale Attic

Soak in the beauty of this professionally designed and newly-renovated minimalistic attic in the heart of Chicago's most hip neighborhoods! Every detail of this home was thought through extensively to provide the perfect experience for our guests. Designer furniture, luxury soaps and amenities, a smart TV, high speed wifi, free laundry on site! A quick walk brings you to amazing coffee shops, trendy restaurants, or hop on the Blue Line train to help you get to any part of the city with ease.

Guest favourite

Home in Chicago

4.89 out of 5 average rating, 113 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

Guest favourite

Cottage in Gary

4.96 out of 5 average rating, 145 reviews

Neon Dunes Vista Beachfront Cottage

Neon Dunes Cottage is perfect for a romantic getaway. A newly renovated cottage with new kitchen, modern appliances and new bathroom all in a bright airy home. It is located in Indiana Dunes National Park/Miller Beach. Only 1.5 blocks to the beach, you can hike trails nearby and come back to relax in a unique, comfortable setting with ambiance and charm. It's perfect for summer/holidays. Wifi, onsite parking and self check in, allow you to enjoy our wonderful home in privacy and peace.

Guest favourite

Rental unit in Forest Park

4.88 out of 5 average rating, 166 reviews

Home in Forest Park upstairs.

In this cozy apartment you will have a small but functional kitchen, in unit laundry, fast WiFi connection and access to a back yard.. It’s an old building but conveniently located 30 minutes from O'Hara International Airport, 20 minutes from Downtown Chicago via I-290, and 40 minutes away from Midway Airport. Forest Park is a very safe, vibrant and diverse suburb of Chicago. You will be within walking distance of many different restaurants, boutiques, bars, parks, and public transit

Guest favourite

Rental unit in Chicago

4.97 out of 5 average rating, 354 reviews

Charming, Spacious 3BR Lakeview Apt Near Transit

This newly remodeled 3-bedroom unit with 1-bath apartment is perfect for both leisure & business travelers. Located on a safe, tree-lined street, in the Lakeview neighborhood, with a completely private entrance of it's own. We are just a 5 minute walk away from the CTA Irving Park Brown Line, which will get you downtown in less than 20min. We are also conveniently close to Wrigley Field, Lake Michigan, Bus Stops, and other great neighborhood shops, restaurants, and nightlife.

Guest favourite

Rental unit in Forest Park

4.95 out of 5 average rating, 293 reviews

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). Our home is a 2-unit building. We live in the downstairs unit but the upstairs is all yours and entirely separate. 1 Dedicated Guest Parking spot (included). Additional Free Parking is available. Great wifi. 3-season back porch. Record Player (Real Vinyl!)

Guest favourite

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 313 reviews

a SIMPLE place

Booking the entire house with 100% privacy. It has 2 driveway parking spaces and street parking. Garage may be available. CHECK-IN and OUT are flexible. I set checkout at 11am (text me if you need late checkout). The space is perfect for a family of 4. It is located about 20 minutes from O'Hare airport and 40 minutes from Chicago downtown. Infants and pets are welcome (please text me for over size pets or more than 2 pets) Play pan is available upon request.

Guest favourite

Guest suite in Chicago

4.89 out of 5 average rating, 102 reviews

Cozy one-bedroom suite in the heart of West Loop

Enjoy your trip to Chicago in the heart of Fulton Market in this cozy, one-bedroom guest suite. Whether you’re visiting friends or here for business, this guest suite is the perfect space to unwind at the end of the day. Grab dinner at Chicago’s top-rated restaurants in Fulton Market and West Loop, all within a 10 minute walk. Go out for the night at some of Chicago’s best bars and nightlife.

Guest favourite

Cottage in Merrillville

4.89 out of 5 average rating, 210 reviews

The Hideaway

This cozy cottage (lodging only, renters only) located 30 minutes from Chicago is located on a private 3 acre property. It’s a private detached cottage that sleeps four. One king size bedroom (sheets supplied), large full bathroom with deep tub (towels supplied), full kitchen (dishes, pots and pans ect supplied) and private parking. Also has its own fire pit for enjoyment.