
Holiday rentals with a patio in Chesterton
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Top-rated rentals with patio in Chesterton
Guests agree: these rentals with a patio are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for rentals with patio in Chesterton
Flat rentals with a patio

Modern 3BR with Private Rooftop & Free Parking
Song’s place was perfect for our family trip to Chicago!

The Sunshine House: Scenic Skies Unit!
Really nice, remodeled home! We loved our stay, the beds were comfy, and we loved relaxing in the living room after our jobs were done. We ate at the bar that was next to the home. AMAZING FOODIES‼️🫶 HIGHLY recommend this place, and look forward to staying again in the future.

Cozy Lincoln Park Studio - Steps to Zoo!
very comfortable apartment and in a great location. Highly recommended!

McCormick 2B/2Ba for up to 6 guests/private Patio
Good place to stay, I would definitely stay here again. This place has a security guard downstairs so it feels safe. The unit was clean and easy to get around the city.

Lovely 1 bed room apartment, all to yourself.
We had a wonderful 7 day stay in this beautiful apartment. It is beautiful, clean, and comfortable. We felt right at home. The living room wa spacious comfortable, with a large TV, and a cozy fireplace unit. The kitchen had everything necessary to cook meals, plus a nice assortment of coffee and tea, along with a Keurig. The bathroom was fresh and clean with plenty of towels. The bedroom had a large, comfortable bed with fresh linens, a large closet, and quiet dedicated workspace. Laundry facility was accessible right outside our door. The area and building were clean and quiet, with a lovely enclosed backyard with picnic table. Cornelius was a very responsive, helpful, friendly host, who answered all our questions, and made sure we had all the information we needed to make our stay fun and easy. Check in process was very simple, and there is ample parking I highly recommend Cornelius and this lovely unit. You will be very pleased with your 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.

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt
Joshua’s place was exactly as shown in the pictures. Beautiful. Great location. He was a flexible and generous host!

CitySlickers Crash Pad /Free Parking /No Clean Fee
Kevin’s place was clean and comfortable. We felt right at home and he was extremely responsive anytime I needed to contact him. I will definitely stay here again! Thank you for having us!
House rentals with a patio

Charming 3-bedroom home-Freshly remodeled-ND 5 mi.
This is a very nice home to stay in whether you're staying in South Bend or need a home base to explore Indiana. Very convenient location and the house is fresh and seemingly renovated. Would highly recommend staying here.

Steps to Beach & Starbucks! Private Yard, Firepit!
This is our second stay in this home. Quaint, clean, and in the heart of New Buffalo. We loved that our dog could join us! Plenty of towels, linens, cleaning supplies, and amenities that made our stay comfortable. I highly recommend!

The Waverly Retreat
My family stayed at the Waverly Retreat for my son's wedding weekend. The location was perfect as the reception was at the Dunes Pavilion. We appreciated the space, cleanliness, attention to details, fully stocked kitchen and Kayla's assistance with everything. The master suite was gorgeous and the bathroom space allowed several of us to get ready at one time for the wedding. Thank you Kayla for a wonderful place to stay!

Casa Gitana - Boutique Style Stay in Three Oaks
Brooke’s place was exactly as described! My friends and I had a relaxing, worry free stay. Her place is interestingly decorated and close to all the things we wanted to do. Beds were comfy and the house was clean! We would stay again!

New Dunes Escape
Probably the best place we've stayed. Clean, organized, and exactly as described. The attention to small details makes you feel at home. Will book again if we go back!

Birch Nest Cottage by The Lake
We loved staying at Katrina’s place! It was very comfortable, clean and uncluttered. We felt right at home the minute we walked through the door. New Buffalo was a short drive away so had a nice dinner at the Stray Dog. We loved spending time down at the beach and then coming home to grill some steaks. Katrina was very helpful and super communicative during our stay! Thank you for a wonderful weekend away!!

UncleLarrysLakePlace HotTubKayaksPingPong
Jamie's place was the perfect getaway! The view of the lake is beautiful, the house is very clean and we had plenty of space for our family of 7. The ping pong table and games were a great touch. Thank you for a lovely and enjoyable experience!

Indiana Dunes, Beach, Chicago, Shopping Center
This was the perfect location for visiting family. Coming from out of town Jessica home was definitely home away from home. She was very responsive. Everything was exactly as listed and photos accurate. The home was clean and peaceful. I will definitely book this home again when I'm in town to visit family.
Apartment rentals with a patio

816 PLZN Luxury Apt | Rooftop | Garage Parking
The host and team were very communicative. The space was beautiful with high ceilings , clean, spacious, and well equipped.

Convenient & Spacious 3BR Condo w/Free Parking
We enjoyed our stay at Yuyi’s. The space was very clean! There is a beautiful park across the street, delicious restaurants all around, and a grocery store 4 blocks away! We traveled in for business and it was perfect for us, Would love to stay again the next time we are in Chicago.

Urban Oasis | Great for Families w/ Kids
Alex was very responsive and incredibly helpful throughout this process as it was our first time using Airbnb and in Chicago. The home was clean although there were a few areas that could use more of a deep clean. The neighborhood was very relaxed but there isn’t a ton to do (no coffee shops or any local shopping) However it’s only a 6 minute drive or 20 minute walk (we walked and it was really nice) to china town or just to view the river. We only stayed 3 nights and we definitely would stay again!

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!
One of my favorite Aibnbs of all time. The location is FUN - right in the center of the action in Northalsted. The space itself is beautiful and clean. The bedrooms are spacious, and the kitchen is well equipped. Allan was awesome and left us a bottle of prosecco to welcome us. Best part of the house is the huge covered front balcony - a front row seat to the joyous crowds, especially on the weekend. We saw a concert, walked to a Cubs game, spoiled the kids on Michigan Ave - and everyone agreed the balcony was our fave part of the trip. The rear deck is icing on the cake. We were in town so our kids could go to a concert and they also loved the area. If you're sensitive to noise, bring earplugs - all the action brings a bit of music - but really it's a steady din so super easy to tune out at bedtime. We love this place and can't wait to come back!

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.

Updated Designer Duplex In Fulton Market W/parking
Supurb stay in Fulton Market! Seth was an outstanding host—responsive, welcoming, and accomidating. The apartment was spotless, well decorated, and thoughtfully stocked with everything we needed for a comfortable stay. The beds and linens were especially cozy, making it easy to relax and feel at home. The location is superb—just steps away from a variety of highly rated restaurants. The location is superb—just steps away from a variety of highly rated restaurants. We also felt completely safe throughout our stay. The neighborhood has a welcoming, upscale vibe, which added to our peace of mind. A quick heads-up: the unit is a second-floor walk-up accessed via a private entry. Inside, as you can see has the spiral staircase; a unique architectural feature, but if you’re traveling with heavy luggage, it’s something to keep in mind. Pack accordingly! 😉 Overall, we had a wonderful experience and would gladly stay here again and agai

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 holiday rentals with a patio in Chesterton
Total rentals
40 properties
Nightly prices starting at
₹6,025 before taxes and fees
Total number of reviews
3.9K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 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
- Willis Tower
- Wicker Park
- Potato Creek State Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Chicago Cultural Center