Vacation rentals with outdoor seating in Chesterton

Find and book unique accommodations with outdoor seating on Airbnb

Top-rated accommodations with outdoor seating in Chesterton

Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

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Guest favourite

Farm stay in La Porte

4.99 out of 5 average rating, 441 reviews

Cabin on Swede Hill

Welcome to "Cabin on Swede Hill". Our family has farmed this land since 1871. My great grandparents, Swan and Johanna Johnson immigrated to America in the 1860's, found this land which was similar to Sweden. They raised their family here. Approximately 65 Swedish families settled in this community, became to be know as the "Swede Hills". We just received the Hoosier Homestead Award from Indiana celebrating the Sesquicentennial Award. We invite you to come...... and experience country life.

Aug. 31 – Sep. 7

$218 CAD per night

Guest favourite

Home in Michigan City

4.94 out of 5 average rating, 401 reviews

Small Clean Home Near Beach, Casino, Outlet Mall

This cozy, clean home is located 2.9 miles to Beach, Outlet Mall, and Casino. Quiet neighborhood. Well maintained property. Perfect for a couple or business traveler. It is not child proof. It is not suitable for small children. There are open stairs that cannot be blocked. We do not accept pets. I have an autoimmune disease. I am allergic to pet dander We request drivers license of each guest. Per Airbnb guidelines I am disclosing we have cameras on exterior north/east of home with audio.

Sep. 19 – 26

$192 CAD per night

Guest favourite

Home in Portage

4.92 out of 5 average rating, 149 reviews

Newly Renovated with Finished Basement

This beautiful house is located near Lake Michigan in Northwest Indiana, less than 10 minutes from the expressway and toll road. There is a stainless steel kitchen, spa bathroom, finished basement and bar with sleeping capacity to accommodate two families. This is a smart home with Ring db, lights and thermostat controlled by your voice. We are less than an hour drive from downtown Chicago, and there are many great beaches nearby. Shopping and great dining options are also within a close drive.

Nov. 19 – 26

$268 CAD per night

Superhost

Camper/RV in Porter

4.79 out of 5 average rating, 609 reviews

'Pool Barn Camper' w/Hot Tub near Indiana Dunes

Pool is open! Hot tub open all year! Fully equipped RV is parked in the driveway of our Pool Barn. RV sleeps 6, has bath w/shower, stove, microwave, heat & A/C, & running water all year. We are located minutes from the sand beaches of Indiana Dunes on Lake Michigan. Hiking in the Indiana Dunes National Park along the Little Calumet River and the historic Bailley homestead is only 1 block away. You may also use our large pool, hot tub, grill, campfire, and playground area. No cleaning fee!

Jan. 27 – Feb. 3

$257 CAD per night

Guest favourite

Home in Michigan City

4.96 out of 5 average rating, 193 reviews

Pottawattamie Place - near Dunes, Beach, & Casino

Escape with family & friends near the dunes of Lake Michigan! You'll love cozy "Pottawattamie Place," located near a variety of attractions. Fully loaded kitchen, backyard firepit, foosball, & fun! Walk to Pottawattamie Park or drive 3 short miles to the sandy beaches. Near tree-lined hiking trails in the nation's newest national park, casino, wineries, boat rentals, cafes, Michigan City Zoo, splash pad and park, outlet malls, & antique shops. Perfect for those who want to relax AND adventure!

Jan. 5 – 12

$233 CAD per night

Guest favourite

Farm stay in De Motte

4.94 out of 5 average rating, 113 reviews

Cozy barn loft on organic vegetable farm

Find peace and restoration in this beautiful barn loft at Perkins' Good Earth Farm. The loft has a bedroom, separate shower and toilet spaces, work area, sitting room, kitchen space, and heating/cooling fresh air system. Located above our farm store, the loft provides privacy for you while giving you access to fresh fruits & veggies, locally sourced meats, homemade soups & salads from our farm kitchen, and so much more. You can also walk our farm trails, visit the veggies, or enjoy a campfire.

Aug. 13 – 20

$130 CAD per night

Guest favourite

Home in Michigan City

4.98 out of 5 average rating, 230 reviews

House of Zen: Peaceful Modern Cabin on Tryon Farm

The House of Zen is an architect designed home situated in the woods, part of a sustainable farm community on 170 acres. Only an hour drive from Chicago, it is the ultimate escape. The perfect getaway for couples, creatives and nature lovers who want some peace, quiet and space. Explore the farm trails & enjoy the wildlife and soothing sounds. Note: We have a 3 night minimum during our high season (mid May-mid September), and open 2 night stays the week prior if we have a couple open days.

Sep. 3 – 10

$323 CAD per night

Guest favourite

Cottage in Valparaiso

4.88 out of 5 average rating, 496 reviews

Flint Lake Cottage.

This is a rustic cottage with old world charm. There are 2 fireplaces,. The home sits on a hill overlooking a lake. The lake can be accessed from the back yard. - Pet free - Earth friendly cleaning products - Private beach & park access - Easy access to city center & university - One hour from downtown Chicago - National Lakeshore and Dunes State Park nearby - Local breweries & award winning restaurants - Biking & hiking trails near by - Wood fire places to enjoy in cold weather only

Dec. 15 – 22

$218 CAD per night

Guest favourite

Barn in Michigan City

4.96 out of 5 average rating, 344 reviews

The Black Pearl Great Escape Spa & Art Shop

Check out our website! thegreatescapespah.com The Black 🖤 Pearl is perfect for a Special Occasion for the Evening. Book a Couples Massage @ 3p.m. & Check into your Spa Suite @ 4 p.m. Kick your feet Up & Order in.... Or Dine Out~ This quaint property is located in a woodsy setting 5 minutes from Lake Michigan. The keyless entry door to The Black Pearl is located on the East wall of The Great Escape. Upon entry the Black Pearl door will be directly in front of you. Mini Luxury awaits!

Jan. 30 – Feb. 6

$201 CAD per night

Guest favourite

Guesthouse in Chesterton

4.96 out of 5 average rating, 114 reviews

Bro’s Place

Welcome if you like country life Bro’s place is the place to be...watching the sheep, chickens and wildlife on you back deck making dinner on the grill with a full kitchen. Pick your own veggies outside the back door when in season. You will find a welcome basket with snacks, wine and homemade soap in bathroom fresh eggs from our chickens when available if your planning to visit our Beautiful Indiana Dunes you’ll find everything you need..chairs, towels, cooler Queen size sofa sleeper

Dec. 23 – 30

$172 CAD per night

Guest favourite

Guesthouse in Chesterton

4.91 out of 5 average rating, 314 reviews

"myhathouse" detached studio downtown Chesterton

Vaulted skylights allow natural light. Ksize bed. Futon opens into a bed. (DEEP cleaned to AirBnb COVID-19 disinfectant standards) Fully stocked kitchen, sm. bathroom w/ shower. Parking ft. of house, 1.5 M from Lake Michigan Shoreline, 2 blocks to 15th St. entry to Prairie-Dune Trail. European Market (May -Oct) each Saturday downtown. Fall season drives along U.S. HW 12 & 20 for foliage Winter day hikes, x-county skis trail, shopping trips to the Michigan City Outlet mall

Jul. 9 – 16

$187 CAD per night

Guest favourite

Home in Chesterton

4.98 out of 5 average rating, 126 reviews

Hotel Whiskey

Fully remodeled and tastefully decorated two bedroom home for short or long term stays. Office space for work travelers. Pet friendly with secure fenced in back yard. Walking distance from downtown with quaint shops, wine bar, craft beer bar, restaurants and bike trails. Whether you're in town for work, visiting family or just looking for a weekend getaway, this house and location are perfect for short or long term stays.

Feb. 1 – 8

$287 CAD per night