
Vacation rentals with outdoor seating in Chesterton
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Top-rated outdoor seating rentals in Chesterton
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Popular amenities for Chesterton outdoor seating rentals
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.

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!

Dunes Vacation Rental
Quiet and peaceful location, our family enjoyed space and attractions nearby. Mark is a great host
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
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!

Restoration Farm - Simple & Sustainable Living
Enjoyee the stay. Could have stayed more than 1 night but thats all we had time for this time. Hosts are responsive and helpful. 100% recommend.

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

ValpoVilla: Location, location, location!
Such a cozy, well-appointed apartment in a great downtown Valpo location, walkable to fantastic coffee (Fluid roasters), boutiques and restaurants. We visited in June and caught the Saturday farmer’s market too! The apartment was scrupulously clean, with crisp white linens. There were fans available (we like the white noise), A/C units (we didn’t need them), ironing supplies and blow dryer. The beds were very comfortable too; in fact, I wanted to know what type of memory foam magic was happening under the fitted sheet! The TV was outfitted Netflix and Prime. We didn’t use the kitchen, but it was clean and well set up. Whoever cares for this property is so attentive to details; the grounds are trim, vibrant and everything is swept. Plus, the building itself is interesting, originating in 1860 (Abe Lincoln days!) and nicely remodeled inside. Hosts were extremely responsive and accommodating. Thank you for the wonderful stay!

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.

Lake Breeze Suite - Beaches, Dunes, Golf, Wine Tr
A wonderful and quiet space.

Second Floor Apartment sitting on Pine Lake
Rhonda has a great setup right on the lake! It’s beautiful! She has a few kayaks and a paddle board for guests. The weekend we were there was GORGEOUS, meaning the lake was full of boats & jet skis zipping around, making kayaking difficult/almost impossible. Next time, we’d definitely look into a boat rental to fully enjoy the lake. Two things to note: going with a pet is a little inconvenient as you need to walk them down the street to go potty. Also, the location isn’t private with the host living onsite. Rhonda is a gem, however! The apartment itself was very clean & stayed cool despite the 90*+ outside. I wish there were a few more spots to hang wet bathing suits/towels.
Condo rentals with outdoor seating

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!

Open 7/4-7/11Perfect Location Condo Pools Walk to
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.

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

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!
Really enjoyed our stay. Melanie was responsive and checked in on us to see how are stay was going and if we needed anything. She explained everything so well beforehand that we didn’t need any help. She was a fantastic host and the place was great. Definitely recommend and would go back!

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!

Serenity on the Shores
Ashley was a great host! She provided clear instructions for check-in/check-out, had nice local recommendations, and was extremely responsive. I also appreciated that she was willing to accommodate my travel dates near the last minute due to a death in my family. The unit was very clean and well-stocked. I loved the beautiful views from each window and the quiet, serene environment. Although I could hear the train at night, it was not super loud - kinda just like background noise. I actually found it to be peaceful (maybe because I’m from the city lol). Would love to visit again! :)
Quick stats about vacation rentals with outdoor seating in Chesterton
Total rentals
30 properties
Nightly prices starting at
R1,446 ZAR 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
- 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