
Vacation rentals with outdoor seating in Chesterton
Find and book unique outdoor seating rentals on Airbnb
Top-rated outdoor seating rentals in Chesterton
Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesterton outdoor seating rentals
House rentals with outdoor seating

Airy and bright, Cottage Blue Welcomes You!
Huge house. 4 big bedrooms. 2 nice size bathrooms. Kitchen was big either plenty of space. Close to beach access and zoo. Quiet neighbor. Restaurants and outlet stores close by. Would recommend staying here! Great host and we enjoyed our time here. Thanks!

Dog Friendly Downtown Three Oaks Cottage! Fenced!
This home was perfect! Very cozy, clean and walking distance to all the great spots in town. Donna was a great host and I cannot say enough great things! Looking forward to staying here again :)

Perfect spot: 3 FULL baths, 4 bedrooms
It is the perfect place for our family with lots of space. We love the yard for the kids to be able to run around. It is also close enough to downtown to walk. Joe is very responsive and accommodating.

Secluded Modern Retreat Near Beach - "Sandlot"
I met my family here for a birthday celebration. The house is stunning, with large windows overlooking two sand-dunes. The light plays through the trees in magical ways. It is so quiet and peaceful that we all slept well. There are so many places to play and relax - from the upper deck loft, to the hot-tub and lots of nooks to read and chill. There are all sorts of activities for kids - both outdoors and indoors. It was a transformative time for myself and our family! Nancy was a fabulous host - always friendly and helpful.

Roomy and Private Getaway for Families & Friends
Very spacious and just as described. Perfect location for visiting family and would be great in the summer!

Pet Friendly Perfect Spring Getaway with Hot Tub!
Great place and as the description suggests, it’s pup friendly! We lacked nothing during our time there and would highly recommend.

Hickory House - 6 BR 2.5 Bath - Walk to Downtown
We had a quick stay but the house & location were perfect. They were extremely responsive & flexible when we needed to make changes (ended up having more people & changed locations). There’s so much to do in three oaks - we’d definitely rent from them again.

3BR w/sauna, tanning bed, hot tub 3.9 miles fromND
loved staying here. Victoria was friendly and responsive. wish we had more time in the unit to enjoy the extras.
Apartment rentals with outdoor seating

Cozy Casa: Downtown Digs!
Perfect stay for us, thank you!

Beautiful European Apartment
I had a wonderful stay! The place was clean, comfortable, and exactly as described. The host was friendly and responsive, making check-in and check-out super easy. The location was great, with easy access to everything I needed. Highly recommend and would definitely stay again!

Cute Skylar: Valparaiso University ShortTerm Stay
Lovely hosts, clean apartment, good location. She also had pretty quick communication when we couldn’t get into the door at first.

Best Location in Hyde Park apartment
A big thank you to our host Jerry for a wonderful stay! Could not ask for a better location, and loved the spacious and comfortable apartment!

Garden Apartment in captivating Hyde Park
Nice location with nearby supermarket, cafes and restaurants. The nearby busstop to go downtown is also very nice and near. Great apartment with all the necessary amenities for short stay. 😁

Restoration Farm - Simple & Sustainable Living
The place is was very nice and clean! Price is worth it and it’s also very relaxing. The hosts were very nice and welcoming too! Would stay here again if in the area!

Spacious Bronzeville Apartment
This beautiful grey stone that Darius kindly shares with visitors is steeped in Bronzeville's rich cultural and diverse history. Darius was an excellent host with prompt assistance on questions. This home is very well maintained, very clean, with many comforts we seek in a home and it has such character. I highly recommend a stay - and I plan to be back.

Morton's Retreat Cozy 1 Bedroom Apartment
Great space and lovely little place to stay at. Noah was super responsive and helpful to everything I needed during my stay. Power went off in half the building and he immediately fixed it! 10/10 recommendation. Hope it’s open for my next trip!
Condo rentals with outdoor seating

A Stones Throw from U Chicago South Campus!
Great location within walking distance of University of Chicago and in a safe neighbourhood. Basement apartment with 2 bedrooms. Bed was comfortable & extra pillows & blankets were provided. Toilet & kitchen facilities were slightly dated but functional. Appreciated the use of washer/dryer & complimentary coffee/tea. Very hospitable host!

Studio flat in the heart of Chicago's Gold Coast
The Price was PERFECT for this beautiful location of GOLD COAST!!

Luxe 2BR Cozy Suite | Skyline Views near McCormick
I liked the place. Just that the reception is not always available. Although they're not needed always, yet at time when we need to drop off the parking key card etcetera, it's hard to wait for them to show up despite waiting for about 20-30 minutes. Otherwise. It's a great place hosted by a decent host.

Downtown Mich Ave #7| Park View Penthouse +gym
Beautiful spot, cannot be be beat, was a block away from our favorite pizza spot and a few blocks from our dumpling place. The rooftop view is stunning, panoramic view of the city. As for the apt — it was very well laid out, maximizing all of the space and the softest couch we’ve had in any Airbnb to date. Hosts were in constant communication and we were only there for a long weekend university visit. Very happy with the place, would use again this summer or for any future visits to the city.

Perfect Location Condo w/Marina Views Pools Walk t
Met expectations in every way. Clean, well maintained condo. Great location with several restaurants within walking distance, and a 10 minute walk to the beach. Beach gear was provided. Well stocked kitchen amenities and board games. Host responded quickly to all emails. Very well run. Easy all the way around.

Nightingale Dunes - Modern beach town retreat
Katherine was absolutely amazing! Very quick to redoing to questions. She gave great instructions, along with a lists of recommendations. Her unit was spotless and cozy. So comfortable that we decided to stay in instead of go out.

Live the marina life in New Buffalo!
Great place for a girls weekend! Nice and spacious perfect place for family as well. Would definitely rent again!

Uptown Penthouse on Pine:By Lake
The penthouse was the perfect spot for a family getaway! Rooms were large and well laid out, kitchen had everything we needed, the Michigan city and new Buffalo had lots of great restaurants for dining out or takeout. Everything was immaculately clean, René was responsive, friendly, and helpful. The outside and the neighborhood do not reflect the gem inside! We had a really comfortable stay, and will definitely be back!
Quick stats about vacation rentals with outdoor seating in Chesterton
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ294 before taxes and fees
Total number of reviews
3.4K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Warren Dunes State Park
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- University of Notre Dame
- Museum of Science and Industry
- 875 North Michigan Avenue
- Lincoln Park Zoo
- Chicago History Museum
- The Field Museum
- Wicker Park
- Potato Creek State Park
- Flossmoor Golf Club
- Willis Tower
- Brookfield Zoo
- Chicago Cultural Center
- Lincoln Park
- Garfield Park Conservatory
- Promontory Point