
Holiday rentals with outdoor seating in Chesterton
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Chesterton
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.
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Popular amenities for Chesterton outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Home newly remodeled minutes from Notre Dame.
How can I put in a few words how we felt about Cary’s house! We loved it immediately, everything outside, everything inside! Absolutely NOTHING was missing. Anything you needed was waited for you to need it. The house is meant to please the pickiest folks . You can’t name a thing that was a disappointment. Where else will you find a garden just waiting for you to pick it??

Dunefarmhouse Modern Country Escape
This is such a beautiful home! Got the chance to unplug and feel right at home within the trees. Lots to do in the area too, went to the zoo, winery, and a brewery. Laurel was great and had a bunch of notes around the home that were super informative and helpful. I would absolutely recommend this place to anyone who’s looking to slow things down and connect with nature.

Boho Chic Coach House 30Min to downtown W/ Parking
I enjoyed my stay. It was clean and pleasant. Marilyn was very friendly and quick to respond to any questions I had. I would recommend staying at this Airbnb! Great time!

The treehouse at Warren Dunes
The excellent taste of the hosts sets this rental apart from the rest. The decor in the home is beautifully curated. When you combine that with the views, it's a perfect vacation spot! We were grateful to be able to return for our fourth visit to Charles and Jeremy's home. Thank you for sharing it with us--we love it!

Small Clean Home Near Beach, Casino, Outlet Mall
We really enjoyed Rina & John’s place while we visited the Indiana Dunes! The home was close to downtown and local restaurants. The home was squeaky clean.

Beach! Hot Tub! New Buffalo! Firepit! King Bed!
Great private space on a quiet street. Lots of breweries and restaurants a quick drive away. Amenities were just as described and the space is in great condition.

Charming Getaway House near Beach
Excellent location in a cute (and quiet) neighborhood just two blocks from a couple of great restaurants and walking distance to the beach. We left very refreshed and relaxed. Everything was as expected or better.

The H'Art of Chesterton
Cute little house uniquely decorated. We enjoyed dinner on the front porch one evening. Well equipped kitchen and bathroom. Great shower. Plenty of comfortable seating inside & out. The hosts were great and made us feel very welcome. Great location for driving to a variety of hiking trails and beaches. Highly recommend “Roots & Bones” restaurant. The food was top notch!
Apartment rentals with outdoor seating

Plant MOOD FREE Wi-fi, parking, washer & dryer!
We really enjoyed our stay. The place was very clean and welcoming. The bathroom had a nice shower with good water pressure. The bed was comfortable and provided a restful sleep. Any questions I had, Siobhan responded very quickly and pleasantly. We went to a beer festival in nearby Munster and this was a great location to stay in.

Modern Apt with style & comfort in Pilsen Chicago
A-MAZ-ING stay! My wife and I had such a blast in Chicago. GOGO was very kind and inviting, good energy! The place was exactly what we wanted with all the amenities. Sparking water in the fridge which was a treat after waking 18k everyday. As a runner, there was plenty of sidewalk and things to see. I recommend running up LEAVITT to 18th street and take 18th down for a nice 3 to 5 mile run. The L train “pink line “ was close and walking back at night we felt relatively safe. I would high recommend staying here in Pilsen area the next time you are in Chicago. Mahalo

Private Entrance Guest Suite on the River
Maybe the best Airbnb attached to someone’s home that I’ve ever stayed in. Such a sweet set up. Very comfortable, clean, private. Thankful for the keurig for coffee and water bottles in the frig. My stay was short but very restful and waking up to have my morning coffee out on the deck and watch the river and the birds was the highlight of my stay. Mark was very good with communicating and gave clear instructions. The Airbnb was easy to find, even in the dark. Of course being attached to their home there was a bit of noise from the kids in the morning but that wasn’t until after 9am and didn’t bother me at all. I’d definitely stay again if I’m in the area!

Charming Unique 2 Bdrm Apartment in Victorian Home
Charming Victorian house in a peaceful and safe neighbourhood. So thankful for the really comfy queen bed - felt like my home mattress!

*A Happy (City) Glamping- walk to train FREE park
The space is exactly as described. Loved how close it was to public transportation. The space is great for a weekend away.

Restoration Farm - Simple & Sustainable Living
Excellent stay! Beautiful, clean, spacious and well stocked with extra towels, blankets and kitchen necessities. Would definitely recommend and return!

Cozy Chalet by Lake MI&Dunes with Fire Pit
Beautiful decor, it was very cozy and clean would definitely come again

Morton's Retreat Cozy 1 Bedroom Apartment
We had an awesome long weekend at Morton's Retreat. We loved visiting Three Oaks and Sawyer, and going on a few short hikes nearby. We especially loved grabbing drinks at the Historian. The Airbnb is on a busy road, but there is a bike path that runs by it and it's a short walk to Luisa's Swedish bakery, which was excellent. The place was clean and even a bit larger than we expected. Great for a relaxing long weekend.
Condo rentals with outdoor seating

A Stones Throw from U Chicago South Campus!
It was a very cozy apartment with a nice set up. Easy access to university of Chicago and the lakefront trail. We really enjoyed our stay!

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Always responded quickly. When we had trouble with front door lock they came out quickly and addressed the problem.

3 BR Summer GetAway, 15mins to Loop+Gated Parking
Close to the green line for easy transportation.

Logan Square Beauty with 2 Bedrooms W/parking
Matt is a great host. Open, responsive and informative…everything you want really when on vacation

Downtown Chicago - Spa Bath, Patio, 3 blocks to L
Great place! Everything was clean, in a good location and they communicated well.

Renovated 2 Bed Condo Lincoln Park w/ Free Parking
John's place is great, just as described. Very clean and location is perfect (across the street from Pequod's). Check in/out was easy and communication was good.

Modern Chicago Movie Themed Apt
We had a fantastic stay at this Airbnb during our Chicago trip! The location was perfect — close to everything we wanted to see and do with our kids. The apartment was clean, well-equipped, and exactly as described. It felt like a home away from home. Check-in was smooth, and the host was responsive and helpful throughout our stay. Highly recommend for families or anyone visiting the city!

Spacious 4 Bedroom Condo
We had a great stay for an extended wedding weekend with our entire family. Adrian's home was clean, modern, and well appointed. The beds were all very comfortable and linens were very soft. We felt very safe and the garage parking spot was a nice addition. I would highly recommend his home and would not hesitate to rebook there in the future.
Quick stats about holiday rentals with outdoor seating in Chesterton
Total rentals
30 properties
Nightly prices starting at
$124 AUD 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
Destinations to explore
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Warren Dunes State Park
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- University of Notre Dame
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Wicker Park
- Brookfield Zoo
- Washington Park Zoo
- Potato Creek State Park
- The 606
- The Beverly Country Club