
Vacation rentals with outdoor seating in Chesterton
Find and book unique outdoor seating rentals on Airbnb
Top-rated outdoor seating rentals in Chesterton
Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

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! 🌞🏖️🌳

Beachfront- Lake Michigan-Hot Tub-Heated Pool
Lake Michigan - Beachfront w/Heated In-Ground Pool- Hot Tub - Indiana Dunes National Park - Private Basement Guest Suite - 2 Bedroom/2 Bathrooms - Beautifully Decorated This guest suite has everything you need for a comfy and relaxing stay. Enjoy the 3-person hot tub, perfect for unwinding after a day of adventure. In the summer months, enjoy the heated, in-ground pool. Hiking, beaches and so much more await—and less than an hour’s drive to Chicago. Heated Pool Open from Mid-May to Mid-Oct.

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. ✌️

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.

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, 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. 💙

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!

Secluded Modern Retreat Near Beach - "Sandlot"
Stunning modern home overlooks private sand dunes on 5 wooded acres just a mile away from beautiful Lake Michigan beaches and surrounded by the Indiana Dunes National Park. Relax in our updated open-concept unique home nestled in the dunes. Enjoy the trails in the backyard, the friendly community, and local attractions near by. Just an hour to Chicago by car or the South Shore train is 1/2 mile from the house, with easy rides to Chicago and South Bend.

The Lake Escape -Cozy Lakefront Cottage Valparaiso
Escape the everyday with a relaxing stay at this cozy cottage located on Flint Lake! Hot tub, pontoon boat, fire pit, gas fireplace, tv, lake front, canoe, kayak, sauna, grill and more. This charming property is lake front with a small 50ft beach area and dock. Use of 2018 Sylvan pontoon boat, canoe, and kayak are included. You will love the lake life. Please note the pontoon boat is only available in season from May 1st to October 1st.

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!)

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.

The Lake Escape - 5 Mins from beach, casino, & zoo
LOW CLEANING FEE! Stay close to the beach, only 1.3 miles away, at our spacious property in Michigan City, Indiana! Luxury amenities include: a large jacuzzi tub, dual shower heads for up to 2 person showers, urinal, a large king size suite with a 65 inch TV, and more! We’re located on 11th St. That means that the South Shore train line runs right in front of our home! It is a no horn zone.
Popular amenities for Chesterton outdoor seating rentals
House rentals with outdoor seating

Lakefront House, Pontoon, Deck, Fire Pit & More!

Dog Friendly Downtown Three Oaks Cottage! Fenced!

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

Life's A Beach! Relaxing ranch close to beach!!!

Aunt Betty's Lakeside Abode, Hot Tub Steam Shower

-The District 5 Schoolhouse-

Best Deal In Michigan City 1.3 miles to Beach

Bayless Dune Lodge at West Beach - Indiana Dunes!
Apartment rentals with outdoor seating

1Plant MOOD FREE Wi-Fi Street Parking Washer/Dryer

The Sunshine House: Scenic Skies Unit!

Cute Skylar: Valparaiso University ShortTerms

Beachcomber Suite - Beaches, Dunes, Golf, Wine Tr

French château -literally 150 steps from BEACH

Cozy Chalet by Lake MI&Dunes with Fire Pit

ValpoVilla: Location, location, location!

Morton's Retreat Cozy 1 Bedroom Apartment
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

Nightingale Dunes - Modern beach town retreat

Live the marina life in New Buffalo!

Lake Condo in the heart of Downtown New Buffalo

Uptown Penthouse on Pine:By Lake
When is the best time to visit Chesterton?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ533 | ﺩ.ﺇ562 | ﺩ.ﺇ518 | ﺩ.ﺇ510 | ﺩ.ﺇ657 | ﺩ.ﺇ698 | ﺩ.ﺇ830 | ﺩ.ﺇ735 | ﺩ.ﺇ628 | ﺩ.ﺇ665 | ﺩ.ﺇ558 | ﺩ.ﺇ569 |
| 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 vacation rentals with outdoor seating in Chesterton

Total vacation rentals
Explore 30 vacation rentals in Chesterton

Nightly prices starting at
Chesterton vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

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

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Chesterton vacation 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!
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Warren Dunes State Park
- Guaranteed Rate Field
- The Field Museum
- Wicker Park
- University of Notre Dame
- Lincoln Park Zoo
- Garfield Park Conservatory
- Oak Street Beach
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Willis Tower
- Washington Park Zoo
- University of Chicago




