Vacation rentals with a patio in Chesterton

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Popular amenities for Chesterton patio rentals

Apartment rentals with a patio

Guest favorite
A modern rooftop deck is presented, featuring contemporary seating with vibrant orange cushions arranged around a firepit. Panoramic views of the Chicago skyline are visible, showcasing a mix of architectural styles under a clear blue sky.
Apartment in Near North Side
4.92 out of 5 average rating, 142 reviews

Modern 3BR with Private Rooftop & Free Parking

JillRating, 5 stars1 week ago
Song’s place was perfect for our family trip to Chicago!
Guest favorite
The outdoor area features a shared backyard with a large picnic table and benches surrounded by decorative gravel. A fire pit is positioned at the center, while string lights add ambiance. The bright yellow house stands in the background, showcasing a welcoming exterior.
Apartment in Michigan City
4.97 out of 5 average rating, 89 reviews

The Sunshine House: Scenic Skies Unit!

SheldonRating, 5 stars1 month ago
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.
Guest favorite
A cozy studio space features a sofa with blue cushions, complemented by a light wooden table and colorful accent wall. Natural light filters through the window, casting soft illumination. A television is positioned on a ledge, with a decorative statue nearby.
Apartment in Lincoln Park
4.84 out of 5 average rating, 277 reviews

Cozy Lincoln Park Studio - Steps to Zoo!

BrianRating, 5 stars2 days ago
very comfortable apartment and in a great location. Highly recommended!
Superhost
A private patio features a fire pit surrounded by comfortable seating, providing a relaxing outdoor space. The skyline view showcases urban architecture, adding to the metropolitan ambiance. The arrangement encourages gatherings, while the fire pit enhances the inviting environment.
Apartment in South Loop
4.77 out of 5 average rating, 102 reviews

McCormick 2B/2Ba for up to 6 guests/private Patio

LouRating, 5 stars1 month ago
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.
Superhost
A spacious living area features a large, L-shaped sectional sofa in a muted tone, accompanied by decorative pillows. A round mirror reflects the soft lighting, while vibrant artwork adorns the walls, contributing to a welcoming ambiance. A patterned area rug adds warmth underfoot.
Apartment in Merrillville
4.88 out of 5 average rating, 98 reviews

Lovely 1 bed room apartment, all to yourself.

ElizabethRating, 5 stars1 week ago
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.
Guest favorite
Two white Adirondack chairs are positioned adjacent to a circular fire pit. The ground is covered with colorful fallen leaves, and trees with yellow foliage provide a natural backdrop. The scene reflects a serene outdoor space ideal for relaxation.
Apartment in Sawyer
4.88 out of 5 average rating, 104 reviews

Morton's Retreat Cozy 1 Bedroom Apartment

ShariRating, 5 stars2 weeks ago
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.
Top guest favorite
A modern kitchen and dining area are highlighted by sleek white cabinetry and stainless steel appliances. A spacious island with two stools provides seating, while a wooden dining table accommodates four. A decorative shelving unit displays various items, enhancing the clean aesthetic.
Apartment in Lincoln Park
4.99 out of 5 average rating, 125 reviews

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt

SumaRating, 5 stars2 weeks ago
Joshua’s place was exactly as shown in the pictures. Beautiful. Great location. He was a flexible and generous host!
Guest favorite
A cozy living room area features a dark leather sofa facing a mounted television on a wooden media console. A round shelf displays books and plants, while a small desk and chair are positioned beside a bright window.
Apartment in Pilsen
4.94 out of 5 average rating, 143 reviews

CitySlickers Crash Pad /Free Parking /No Clean Fee

JasmineRating, 5 stars3 days ago
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

Superhost
A modern kitchen is shown with stainless steel appliances and white cabinetry. Counter space is available alongside a dining table set for four. Light fills the room through windows, and a cozy seating area is visible in the background, enhancing the open layout.
Home in South Bend
4.87 out of 5 average rating, 154 reviews

Charming 3-bedroom home-Freshly remodeled-ND 5 mi.

DavidRating, 5 stars2 weeks ago
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.
Guest favorite
A fenced outdoor area features a gravel surface with a fire pit and two wooden benches. A green putting green is visible on one side. A covered deck provides shade and houses a grill. Nearby, trees and shrubs enhance the natural setting.
Home in New Buffalo
4.95 out of 5 average rating, 173 reviews

Steps to Beach & Starbucks! Private Yard, Firepit!

NicoleRating, 5 stars1 week ago
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!
Guest favorite
A spacious corner lot features a well-maintained house surrounded by lush greenery and blooming flowers. A paved driveway leads to a two-car garage, while tall trees provide shade to the property. The vibrant flowers in purple add a pop of color to the landscape.
Home in Porter
4.88 out of 5 average rating, 41 reviews

The Waverly Retreat

JohannaRating, 5 stars2 weeks ago
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!
Top guest favorite
A comfortable living space features a vintage green cabinet and a wooden dining table surrounded by black chairs. Natural light floods the room through large windows, enhancing the cozy atmosphere created by soft furnishings and decorative plants.
Home in Three Oaks
4.97 out of 5 average rating, 177 reviews

Casa Gitana - Boutique Style Stay in Three Oaks

KimberlyRating, 5 stars2 days ago
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!
Guest favorite
A modern kitchen space is presented, featuring a large dining table accompanied by black chairs. White cabinetry and light countertops provide a bright appearance, while decorative elements like a shelving unit and fixtures enhance the welcoming aesthetic. Natural light is allowed in through a nearby window.
Home in Porter
4.89 out of 5 average rating, 89 reviews

New Dunes Escape

EmilyRating, 5 stars1 week ago
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!
Top guest favorite
The exterior of the Scandinavian cabin is surrounded by lush greenery, showcasing tall trees and a gently winding path. Sunlight filters through the leaves, casting a warm glow on the dark-colored wooden structure with large windows. A sense of tranquility is created by the natural setting.
Home in Michigan City
4.97 out of 5 average rating, 38 reviews

Birch Nest Cottage by The Lake

MelissaRating, 5 stars6 days ago
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!!
Top guest favorite
A wooden deck offers a serene view of the lake, framed by lush trees. A glass table with metal chairs sits ready for outdoor dining, while a vibrant sunset casts warm hues over the water, inviting relaxation and reflection.
Home in La Porte
5 out of 5 average rating, 94 reviews

UncleLarrysLakePlace HotTubKayaksPingPong

LaniRating, 5 stars3 weeks ago
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!
Guest favorite
A spacious living room is visible, featuring a burgundy sofa and a brown recliner. A wooden coffee table sits in front, adorned with a small floral arrangement. The dining area is adjacent, showcasing a rectangular table surrounded by six chairs. Light-colored walls enhance the room's brightness.
Home in Portage
4.93 out of 5 average rating, 83 reviews

Indiana Dunes, Beach, Chicago, Shopping Center

CheronRating, 5 stars3 weeks ago
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.

Condo rentals with a patio

Superhost
A modern living area is presented with large windows allowing ample natural light. A navy sofa sits beside a decorative coffee table on a patterned rug, with a stylish mirror and television mounted on the wall. The space features sleek wooden accents for a contemporary feel.
Condo in Pilsen
4.84 out of 5 average rating, 134 reviews

816 PLZN Luxury Apt | Rooftop | Garage Parking

HasimeRating, 5 stars1 month ago
The host and team were very communicative. The space was beautiful with high ceilings , clean, spacious, and well equipped.
Guest favorite
A modern living area features a light-colored sectional sofa adorned with blue accent pillows. A round black coffee table is positioned in the center, resting on a decorative rug. Two lamps and a piece of coastal-themed artwork complement the bright, airy atmosphere.
Condo in Pilsen
4.9 out of 5 average rating, 116 reviews

Convenient & Spacious 3BR Condo w/Free Parking

AlexisRating, 5 stars2 weeks ago
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.
Guest favorite
A spacious modern family room features a large sectional sofa adorned with decorative pillows. A 76” smart TV is mounted on the wall, displaying a beach scene. Natural light enters through multiple windows, illuminating the open layout that flows into a dining area with sleek furniture.
Condo in Pilsen
4.94 out of 5 average rating, 125 reviews

Urban Oasis | Great for Families w/ Kids

MelissaRating, 5 stars3 days ago
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!
Top guest favorite
A modern living area features a spacious couch with a textured throw, positioned near a wall-mounted TV above a sleek fireplace. Large sliding glass doors lead to an outdoor patio, revealing a view of the vibrant neighborhood.
Condo in Lake View
4.98 out of 5 average rating, 118 reviews

💥IN THE ACTION!💥 2 Bed, 2 Bath on Northalsted!

RebeccaRating, 5 stars1 week ago
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!
Guest favorite
An inviting living area features hardwood flooring and large windows allowing natural light. A plush sofa with dark cushions is complemented by a unique accent chair. A contemporary chandelier hangs from the ceiling, and a mirror is mounted on the wall, reflecting the cozy ambiance.
Condo in Woodlawn
5 out of 5 average rating, 39 reviews

University of Chicago Condo-Upgraded and Spacious

TiaraRating, 5 stars4 weeks ago
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!
Top guest favorite
A waterfront view is presented from the balcony, featuring a marina with multiple boat slips. The scene is complemented by a wooden table and chair set, inviting relaxation. Lush greenery lines the pathway, and a clear blue sky enhances the tranquil atmosphere.
Condo in Portage
4.99 out of 5 average rating, 91 reviews

Luxury Waterfront 2 Bedroom Condo by Lake Michigan

LucindaRating, 5 stars6 days ago
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.
Guest favorite
An aerial view captures the airy living area featuring large glass doors that invite natural light. A modern gray sofa is positioned beside a round coffee table. The wood dining table in the foreground is surrounded by colorful chairs, enhancing the open layout of the space.
Condo in West Loop
4.96 out of 5 average rating, 230 reviews

Updated Designer Duplex In Fulton Market W/parking

NicoleRating, 5 stars2 weeks ago
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
Guest favorite
A marina scene is presented with a collection of boats moored along wooden docks. The sky transitions from warm orange to soft purple hues at sunset, reflecting gently on the water's surface. Pathways are visible, lined with subtle lighting for evening strolls.
Condo in Portage
4.83 out of 5 average rating, 47 reviews

Serenity on the Shores

KelseyRating, 5 stars1 week ago
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 a patio in Chesterton

  • Total rentals

    40 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 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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