Cottage vacation rentals in Chicago

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Chicago

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Cottage in Highland Park

4.96 out of 5 average rating, 48 reviews

Re-imagined 1880s cottage by Highwood, Metra, Lake

Step inside Step back in time Cozy, 1880 built, re-imagined, ravine edged garden cottage Your home away from home. Escape the city and relax in our newly renovated historic cottage and gardens. Peaceful yet centrally located, vintage yet modern, Mere Cottage has so much to offer. Inside: You'll enjoy updated amenities in harmony with a distinctive vintage charm. The common area has an open layout, perfect for socializing. The kitchen and pantry (my favorite room!) are new from top to bottom and are fully stocked with any cooking gadgets you may need. Two bedrooms are joined by a Jack & Jill bathroom. The living room has a sofa that pulls out into full size bed. Outside: Jordan and I had fun redesigning the grounds from front to back. Enjoy the front garden from the rocking chair on our wrap around porch. Out back we've added a vegetable and perennial garden for you to take in. Dinner out on the back deck overlooking the garden is highly recommended! Guests have access to the entire home and grounds. Jordan and I live in the neighborhood and will be available if you need us! Our cottage is located in Highland Park, about 25 miles north of Chicago on Lake Michigan. We like to think we have the best of both worlds- being in a quiet residential neighborhood with walking access to numerous amenities right around the corner. We're a quick 5 minute walk to Highwood (the north shore’s restaurant district) and an 8 minute walk to the Metra train that can take you from Chicago to Kenosha and any place in between. We're also right on the North Shore bike path (bring your bikes!). Fort Sheridan is also close by and worth exploring for its interesting history, architecture, and nature trails. On foot: Many errands can be done on foot. We have some of the best restaurants and watering holes north of Chicago within walking distance. There is also a Walgreens convenience store 2 blocks away. By car: Getting around by car is also easy. Parking is readily available almost anywhere you'll visit. You can get to downtown Chicago in 30 minutes in ideal traffic. Train: The Metra (our train system) can also conveniently get you to and from various attractions including downtown Chicago (a scenic 45 minute ride), Ravinia music venue, the Chicago Botanic Gardens, Great Lakes Naval Base and many more. Bike: Pack your bikes! We're located on the north shore bike trail. Head north on the trail to check out the beautiful Fort Sheridan, Lake Forest, and quaint Lake Bluff. Head south to Ravinia, Chicago Botanic Garden, and numerous other beautiful villages along Lake Michigan. I bike often and will gladly point you to some great hidden gems! If you're flying into O'hare, we recommend taking an Uber to our cottage. We're about a 30 minute drive from the airport. Six Flags Great America is also a 25 minute drive away. Keep in mind that the bathroom is a Jack & Jill and is accessed from either bedroom. There is no access from the common area, so it could pose an issue at night when sleeping our max number of 6. Please keep things tidy and wash any dishes used during your stay. Out of respect for our neighbors (this home is located in a quiet residential neighborhood), no parties or large gatherings are allowed. No pets allowed.

Aug 13 – 20

$245 per night

Guest favorite

Room in Chicago

4.96 out of 5 average rating, 259 reviews

Top floor of a city cottage (up to 6 guests)

This 3rd-floor is spacious (324 sf) and airy. Nice neighborhood, ample street parking. Private bath on 1st floor. Also: Kitchenette (micro, minifridge, toaster, coffee); water service; I wash your plates/utensils. Sofa sleeper + air mattresses enable up to 6 guests. WiFi and newer tv than in the pictures; free Sling, Prime + Hulu streaming. 45 min by el to downtown, 15 min bike to the lakefront, and 5 min walk to 3 breweries. Walkable fun neighborhoods nearby: Andersonville and Lincoln Square.

Sep 30 – Oct 7

$50 per night

Guest favorite

Room in North Riverside

4.92 out of 5 average rating, 171 reviews

The Albany Park Room at the Cape Cod in Riverside

The Cape Cod in Riverside is approximately 15m away from downtown Chicago. Accessible by public transportation, a block away to a trail entrance and a mile away from Brookfield Zoo. Riverside's historic downtown is just around the corner, so does Loyola University Medical Center. The Albany Park Room is 1 of 2 rooms listed on AirBnB - the other one is the Sable Creek Room; both rooms have a maximum capacity of two guests. Heat and hot water in the property are partially run by solar energy.

Apr 20 – 27

$64 per night

Guest favorite

Room in North Riverside

4.95 out of 5 average rating, 246 reviews

The Sable Creek Room at the Cape Cod in Riverside

Consider my home your home away from home! The Cape Cod in Riverside is approximately 15m away from downtown Chicago. It is accessible by public transportation, a block away to the entrance of a trail and a mile away from the Brookfield Zoo. Riverside's historic downtown is just around the corner, so is Loyola University Medical Center. The Sable Creek Room is 1 of 2 rooms listed on AirBnB - the other one is the Albany Park Room; both rooms have a maximum capacity of two guests.

Aug 31 – Sep 7

$71 per night

Guest favorite

Cottage in Barrington

5.0 out of 5 average rating, 60 reviews

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!

Nov 25 – Dec 2

$255 per night

Cottage in Naperville

New place to stay

Home: Your Cozy Getaway

Welcome to Naperville Nook, where comfort meets convenience in the heart of Naperville. Our guest house offers a cozy retreat for travelers seeking a tranquil escape. Nestled in a peaceful neighborhood, yet just minutes away from downtown attractions, shops, and dining, our space provides the perfect balance of relaxation and exploration. Plus, being walking distance from the metro to Chicago, guests can easily explore the vibrant cityscape.

Jun 8 – 15

$128 per night

Room in West Chicago

Klara's Cottage

A private home situated on an acre of land located centrally between Chicago and the farmers of Illinois. The activities surrounding us is endless: prairie paths for walking or biking, museums furthering one's education, shops galore to puruse or purchase, or fields to rest the weary body while cloud, star and/or airplane gazing. We welcome you to experience a taste of our unique life as fellow sojourners on terra firma.

Jun 6 – 13

$60 per night

Guest favorite

Cottage in Merrillville

4.89 out of 5 average rating, 184 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.

Oct 5 – 12

$84 per night

Guest favorite

Cottage in Fox River Grove

4.94 out of 5 average rating, 51 reviews

Little Fox Cottage - A Cozy Riverview Getaway

A cozy getaway in the Northwest Suburbs of Chicago. Located 40 miles from the city and just 1.25 miles from the Fox River Grove Metra stop. Get away from the city or 'work from home' in our 1 bedroom cottage with a giant covered outdoor space tucked against the slope of a beautifully terraced hill.

Mar 19 – 26

$204 per night