
Holiday rentals with outdoor seating in Chesterton
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Chesterton
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

Visit LakeMichigan Beach-Brewery-Casino-OutletMall
Explore the beautiful Indiana Dunes National and State Parks. Book your stay at this cozy, newly renovated 2 bedroom home centrally-located for all your adventures. Within 2 miles of beach, restaurants, brewery, winery, casino, concert venue, spa, botanical garden, splashpad, zoo, boat tours, kayak rental. Bonus trip: take the Southshore commuter train to Chicago for the day. Here, you can explore all the south shore of Lake Michigan has to offer then kick back at your home away from home. 💙

Blue Birdhouse - Indiana Dunes
Welcome to The Birdhouse - Your Perfect Getaway! 🐦🌿 Nestled near the Indiana Dunes National Lakeshore, our cozy 2-bedroom, 1-bathroom home is perfect for families, couples, and nature lovers. Enjoy a pet-friendly, fully fenced yard, free parking for 2 vehicles, a fully equipped kitchen, laundry, and a BBQ grill with patio for outdoor dining. Minutes from Lake Michigan beaches, hiking trails, and local dining, it’s the ideal spot for beachgoers and adventurers. Book your stay today! 🌞🏖️🌳

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, and close to Indiana Dunes National Park, 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 stay during summer, but open up 2 night stays 1-2 weeks before if possible.

South Shore Studio Apartment {National Park}
I have to warn you definitely not a hook up spot or party house!!! typically rise with rooster on this 5 acre country setting with a small fishing pond. 420 friendly .. Quiet hours are 11 -8 generally some music playing, musicians are welcome !! if you happen to book on a Sunday i host an Open Mic in my Barn every Sunday ..... pretty relaxed. Upon arriving, turn into the driveway, and then right into the yard. Apartment is upstairs, the door is open with the keys inside. ✌️

Relax - SW Mi Getaway/Hot Tub-Beaches & Wine Tours
Welcome to "Lake 2 Grapes" Bridgman is a little gem located between St. Joe and Warren Dunes. Minutes to Lake Mi. beaches, craft breweries, and wine trails. Relax in the upper level of our bi-level vacation home w/private entrance. This 3 bedroom, 2 bath includes a beautiful Master suite! Enjoy the Hot tub and fire pit in the backyard. Wine Tour? Stay with us and you'll receive a discount with "Grape & Grain Tours" plus complimentary pick up and drop off. Must be 25 or older to book.

The Sunshine House: Breezy Beach Unit!
Welcome to Breezy Beach, a bright and cheerful first-floor apartment in the Sunshine House 🌻. With updated amenities, colorful décor, and a prime location near the beach, outlet mall, restaurants, and parks, this spot is perfect for couples, friends, or small families (up to 4 guests). Cook a meal in the fully stocked kitchen 🍳, relax in the comfy queen bed, or enjoy evenings by the outdoor firepit & picnic table. Everything downtown Michigan City has to offer is just a short walk away!

Bro’s Place 6 mile drive to Indiana Dune’s
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

"myhathouse" detached studio downtown Chesterton
Vaulted skylights allow natural light. Ksize bed. Couch opens into a full size 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.

The Dune Den! Huge Yard/Firepit/Near Town+Dunes
Right in-between The Dunes National Park and downtown Chesterton, you will be close to everything when you stay at this centrally-located home. Things to look forward to: Less than 10 minutes to the Dunes and beaches or head 3 minutes the other way to downtown for food, drinks and plenty of small town fun. This charismatic home greets you with all new furniture, front porch, HUGE fenced yard, and local decor. You will fall in love with this family town so bring the kids!

Cute Skylar: Valparaiso University ShortTerms
Welcome to Skylar's Relaxing Spot! This cozy one-bedroom on the second level features a queen-size bed, its own entrance, deck space, and building laundry facilities. Perfect for accessing downtown and Valpo University. Enjoy strong WiFi for remote work and relaxing movie nights on the TV. Located near Route 30 and I-49, it’s an hour from Chicago and 15 minutes from Indiana Dunes, close to malls, ice cream parlors, and great restaurants! ☺️

IT'S THE WRIGHT PLACE
Private guest house newly remodeled. One bedroom queen bed, bath w/shower, full kitchen stocked, including microwave and Keurig coffee maker pods included, family room TV, and WIFI. No matter if you are in town for work, sport competition, family or just vacationing we offer all the comforts of home. Air Mattress available upon request. Please treat as your own home, follow all house rules. No party or gatherings. This is a no smoking home.

Flint Lake Cottage.
This is a rustic cottage with old world charm. There are 2 fireplaces,. The home sits on a hill overlooking the channel that leads to Flint Lake. - Pet free -May not be appropriate for people with mobility issues. - 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 - Wood fireplaces (winter only!)
Popular amenities for Chesterton outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Duplex | Firepit | Game Room | Hot Tub-all year

Anna's Cottage

Couples alert! PVT beach access, hot tub, firepit!

Secluded Modern Retreat Near Beach - "Sandlot"

Dunefarmhouse Modern Country Escape

Casa Gitana - Boutique Style Stay in Three Oaks

The treehouse at Warren Dunes

-The District 5 Schoolhouse-
Apartment rentals with outdoor seating

1Plant MOOD FREE Wi-Fi Parking Washer/Dryer

Beachcomber Suite - Beaches, Dunes, Golf, Wine Tr

French château -literally 150 steps from BEACH

Cozy Hideaway: King Bed, Fire Pit, 7 min to beach

Cozy Chalet by Lake MI&Dunes with Fire Pit

ValpoVilla: Location, location, location!

Morton's Retreat Cozy 1 Bedroom Apartment

King Bed Retreat, Minutes to Beach & Dunes
Condo rentals with outdoor seating

Lakeside Serenity: One-Bedroom Villa

Updated Cottage Downtown, walk to Beach

MTM Premier Properties-on acres of tranquility

Perfect Location Condo Pools Walk to all Beach 1.5

The Broadway Special - 2 Bd/1 Bath Smart-Condo!

Nightingale Dunes - Modern beach town retreat

Live the marina life in New Buffalo!

Lake Condo in the heart of Downtown New Buffalo
When is the best time to visit Chesterton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $205 AUD | $217 AUD | $200 AUD | $197 AUD | $254 AUD | $269 AUD | $320 AUD | $283 AUD | $242 AUD | $257 AUD | $215 AUD | $220 AUD |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about holiday rentals with outdoor seating in Chesterton

Total holiday rentals
Explore 30 holiday rentals in Chesterton

Nightly prices starting at
Chesterton holiday rentals start at $85 AUD per night before taxes and fees

Verified guest reviews
Over 3,900 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Chesterton holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesterton rentals

4.8 Average rating
Chesterton stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Chicago Holiday rentals
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- Rentals with a fire pit Chesterton
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- Rentals with a washing machine and dryer Chesterton
- Rentals with a patio Chesterton
- Family-friendly rentals Chesterton
- Pet-friendly rentals Chesterton
- House rentals Chesterton
- Rentals with outdoor seating Porter County
- Rentals with outdoor seating Indiana
- Rentals with outdoor seating United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- 875 North Michigan Avenue
- Soldier Field
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Warren Dunes State Park
- The Field Museum
- University of Notre Dame
- Wicker Park
- Lincoln Park Zoo
- Oak Street Beach
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- Washington Park Zoo
- Silver Beach Carousel




