
Holiday rentals with outdoor seating in Chesterton
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Top-rated rentals with outdoor seating in Chesterton
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.
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Popular amenities for outdoor seating rentals in Chesterton
House rentals with outdoor seating

Pet friendly stylish retreat with sauna, hot tub
My wife and I have stayed at many vacation home rentals over the years, this one was one of the very best! First, I booked they house late afternoon on the day we wanted to arrive. Sarah responded immediately, accepted our booking and got me the access code to the property. It was all done within a few minutes! The house was beautifully decorated (my wife loved it and she is a designer!), well appointed and located very conveniently to all of the places we wanted to spend our time. We loved the hot tub, used the sauna almost every morning and our Golden Doodle loved the big fenced in back yard. Sarah and Brady are unbelievably responsive to needs too! One evening we wanted to enjoy the fire pit, but they were out of fire starters. I contacted Sarah at 7:36p, she responded at 7:37p and by 7:51 Brandy had already dropped a box of fire starters on the front porch! What?!?!?! Amazing. I HIGHLY recommend this place, we will be back!

Lakefront House, Pontoon, Deck, Fire Pit & More!
I rented Leah's home for my son's. They love to fish and Leah's home was the perfect place. They enjoyed the pontoon boat and sitting around the bonfire. The house was clean and kitchen equipped with everything needed for their weekend of grilling. Leah was a perfect host. Thank you, Michelle

Couples alert! PVT beach access, hot tub, firepit!
An absolutely beautiful stay! Many amenities to make it a comfortable stay! Beautifully decorated! Comfortable bed! Wonderful nights spent n the relaxing hot tub! Enjoyed a great fire pit one night too. Loved the private beach-so peaceful and relaxing! Looking forward to coming back!

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.

Captain's Quarters - Walk to Downtown New Buffalo!
Perfect stay for two families. Lots of room and convenient to all the spots in New Buffalo!m. Will definitely be back!

Small Clean Home Near Beach, Casino, Outlet Mall
My wife and I looked for a place to stay as we celebrated our 11-year anniversary for a night away from the kids — and Rina and John’s place was just what we were looking for! We had all we needed, felt comfy and at home, and enjoyed some snacks and a movie after a day of being out and about. If we ever go back to Michigan City, we’ll definitely look up Rina’s place again. 10/10 recommend!

Blue Birdhouse - Indiana Dunes - No Cleaning Fee
Michael has a great place that is very close to the Indiana Dunes. His directions for how to find the house were easy to follow. It was perfect place to be with my small dog and husband for a weekend away. It had everything you might need for meals in, spaces were well cleaned and well taken care of. We appreciated the small touches that were available to us. The train noise that was mentioned in previous reviews is not noticeable unless you’re outside. I don’t think we heard it at all indoors.

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.
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.

Private Entrance Guest Suite on the River
Great place. I wish I would have gotten there at check-in time, so I could have enjoyed the river more!

Best Location in Hyde Park apartment
Spacious and clean place in the quiet, convenient and safe area! The host is very friendly and response quickly when you have any questions!

Garden Apartment in captivating Hyde Park
It was very well maintained, and the apartment felt very peaceful. The area is also very nice, everything you could need is within 10 minutes walking distance.

Beachcomber Suite - Beaches, Dunes, Golf, Wine Tr
Cute apartment, close to downtown Bridgman. Check in and out was very easy. Larry was communicative. I would definitely stay there again.

Restoration Farm - Simple & Sustainable Living
Loved my stay! The farm was gorgeous and so peaceful and rejuvenating. Wish I could’ve stayed longer and would definitely stay again. Dan and Suzanne were friendly and helpful and the apartment was comfortable, well-equipped and beautifully decorated. 5 stars!

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.

Second Floor Apartment sitting on Pine Lake
We had an amazing time! Me and my boyfriend stayed for one night, the patio and dock were super cozy and we really enjoyed sitting out there at night just listening to music and having some drinks. Super nice area, the beach isn't too far and they have some fun bars and restaurants in the area. Overall, we really enjoyed our stay.
Apartment 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!

Spacious two bedroom condo with a cozy feel!
The place was big, well kept and clean. It was easy to communicate with the host and there are free Netflix in the rooms.

Bright 2BR/2BA, 8 min Walk to ND, 2 Parking Spots
Highly recommended! Conveniently located for Notre Dame (go Irish!), pristine condition, kitchen & bathrooms well supplied, comfy & relaxing atmosphere. Very responsive host (one minor issue was fixed the same day with great communication). It was above our expectations - look forward to staying again!

The Broadway Special - 2 Bd/1 Bath Smart-Condo!
Loved the place!! Newell was very helpful , beautiful home!

University of Chicago Condo-Upgraded and Spacious
I had a wonderful stay! The place was exactly as described—clean, cozy, and in a great location. The host was super friendly and responsive, which made the whole experience smooth and welcoming. I especially appreciated the thoughtful touches like I’d definitely stay here again and highly recommend it to others!

Luxury Waterfront 2 Bedroom Condo by Lake Michigan
This condo was super-clean. We loved the balcony, where we could relax after climbing dunes with our grandkids! Good mattresses (our daughter & husband took the upstairs bedroom) and we appreciated the king-sized beds. There is quite a tall stairway to climb to get to the 2nd floor. Otherwise, easy access (we used the August app) from the parking lot.

Live the marina life in New Buffalo!
We stayed here for my sisters bachelorette weekend, it was perfect! Everything is within walking distance or a short drive away! Would definitely come 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 holiday rentals with outdoor seating in Chesterton
Total rentals
30 properties
Nightly prices starting at
₹6,892 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
- 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
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Wicker Park
- Willis Tower
- Potato Creek State Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Chicago Cultural Center