Holiday rentals in Calumet Park

4.86 out of 5 average rating, 107 reviews

Guest suite in Chicago

Comfortable and Cozy Suite in Quiet Neighborhood

Are you coming to town to visit family, friends or for business? This cozy, clean, comfortable & 420 friendly suite has all you need to escape your everyday. Look no further! This one-bedroom suite is perfect for 1-3 people, small families, or individuals. If you're visiting family or friends and want your personal space or are in town for business and need a comfy bed, wifi, and office space, then this place was designed for you. Kick back and relax in this calm, stylish, 420 friendly space.

5 out of 5 average rating, 13 reviews

Home in Pullman

3 BR/2BA-Pullman Victorian Cottage-Time Capsule

FULL REHAB JUST COMPLETED/transformed into a cozy Victorian home in Chicago’s unique Pullman Village. House is an 1800's time capsule rowhouse (called “cottage”) & the only truly period Pullman home on AirBnB, reflecting the area's Historic Landmark status. Stay here for a truly immersive extension of a visit to Pullman's National Park or the area's new walking tours. Ideal for train/history/architecture/Park buffs, or just a quiet, unique place to unplug & live like olden days with loved ones.

4.85 out of 5 average rating, 20 reviews

Flat in Worth

Charming 1-Bedroom in Worth, IL

Welcome to your cozy retreat in Worth, IL! This newly remodeled one-bedroom apartment is perfect for a comfortable and convenient stay. Inside, you’ll find a spacious bedroom with a queen bed, fully equipped kitchen with brand-new stainless-steel appliances, an updated bathroom with modern fixtures, and two Smart TVs and highspeed Wi-Fi. Conveniently situated in the South Suburbs of Chicago near shops, parks, and dining, you’ll also have easy access to major highways and public transportation.

4.85 out of 5 average rating, 86 reviews

Townhouse in Pullman

Large Executive Row house in Historic Pullman

Charming well appointed home w/exquisite furnishings. Safe, family friendly neighborhood w/shopping nearby. Walking distance to train station. Private entrance w/large rooms & plenty of space to host larger groups. We have everything from soaps to seasonings. Top quality new beds mattresses & linens. Walk to Pullman National Monument with visitors center staffed by US Park Rangers that feature state of the art interactive exhibits that appeal to all ages. Guided walking tours available.

4.88 out of 5 average rating, 152 reviews

Home in Chicago

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.

4.95 out of 5 average rating, 117 reviews

Flat in Beverly

Chicago Charming Historic Beverly Retreat

This comfortable quaint second-floor 2 bedroom apartment rental is situated in a unique historic diverse Chicago Southside neighborhood, namely Beverly/Morgan Park. This neighborhood’s beauty is visible in its hilly tree-lined streets with an array of architectural-style mansions that snake along the popular Longwood Drive. Directly adjacent to the building is a public commuter train that is a short ride to “Millenium Park” in downtown Chicago. Reference # - R2000115152

4.96 out of 5 average rating, 89 reviews

Flat in Beverly

Beverly Cottage Loft

Whether you're looking to stay near family or be close to downtown, our place has it all. This tranquil cottage is located in Beverly which is one of the safest neighborhoods in the city of Chicago. Downtown is a quick 20 minute drive and there are also many restaurants and bars in this area. This cottage has been renovated and have all the essentials you need. All you need to do is unpack your bags and enjoy your vacation. The space is modern, clean, and cozy.

4.82 out of 5 average rating, 210 reviews

Home in Blue Island

Warm and comfortable inviting Suburban home !

160 year old land mark community, Framed cedar bevel siding 2 story home, front porch , 10 ft high ceilings, kitchen canned lighting home. 6 feet fence In closed yard, whole house water filtration system , Quite neighborhood with sidewalks . 19 miles to downtown Chicago , Metra train station and bus route, in walking distance . driving to the city of Chicago 5 minutes to major expressways . Host is willing to be available for any and all information 24/7.

5 out of 5 average rating, 13 reviews

Home in Chicago

Unique 2-bedroom retreat!

Welcome to our stunning Airbnb retreat in the heart of a charming family-friendly neighborhood, and located blocks from the Beverly historic district! This newly renovated gem is designed to provide the ultimate comfort and convenience for your stay. With two bedrooms that can comfortably accommodate four guests, you'll feel right at home in our space. NO LOCAL RESERVATIONS ALLOWED! NO EVENTS OR PARTIES ALLOWED!

4.97 out of 5 average rating, 61 reviews

Flat in Hickory Hills

Cozy Guest Suite. Private Entry+ Turo Rental

3600 sqf single family home with a Guest Apartment and private entry on the ground level. Your family will be close to everything when you stay at this centrally-located place. Centrally located off of I294, I55, I57 and I80. Easy to and from travel. In Need of a rental we have 2018 Jeep Grand Cherokee High Altitude at the house and listed Turo.

4.81 out of 5 average rating, 108 reviews

Flat in Chicago

2 bedroom lovely spacious Suite

This stylish place to stay is perfect for any event. 420 friendly. Come and let us pamper you. Come and enjoy are tree lined community in the historical Beverly community. This Suite has all the latest amenities and beautifully furnished. Make some memories at this unique and family-friendly place.