Vacation rentals with a patio in Chesterton

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Top-rated patio rentals in Chesterton

Guests agree: these patio rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
A clear, geodesic dome is set on a paved patio surrounded by a grassy area and decorative plants. The backdrop features a tranquil lake and lush trees, illuminated by a colorful sunset sky.
Guesthouse in Valparaiso
4.98 out of 5 average rating, 112 reviews

Unique Dome Retreat by Indiana Dunes w/ Lake View

Escape to our Valparaiso Lakeside Retreat with king bed, lake views, unique dome experience, fire pit, grill & hot tub, all near Indiana Dunes National Park, Valparaiso University & 4 local parks! Experience a nature getaway at our newly renovated lake guest house on the ground level of our home with keyless entry & unique outdoor amenities, ideal for friend groups, small families, business travelers & couples. 10 min - downtown Valparaiso. Book now to experience this unique tranquil retreat.

Superhost
A spacious log cabin is surrounded by lush greenery, featuring a large front deck and multiple large windows. The roof has a classic gable design, and the exterior is clad in dark wood, providing a rustic charm. The lawn is well-kept, enhancing the cabin's inviting presence.
Cabin in Portage
4.93 out of 5 average rating, 127 reviews

Cozy Log Cabin Near Indiana Dunes & Lake Michigan!

Less than 10 minutes from Indiana Dunes National Park and Lake Michigan, our beautiful log cabin sits on 2 acres while still being in the heart of Portage! Our large front deck overlooks state land giving a beautiful, private view out of our large windows. Our cozy cabin has 3 bedrooms and 3.5 bathrooms with fun, thoughtful touches for your family including video game consoles, movies, books, a LOT of games, a pool/ping pong table, 2 fire pits, and more! Age limit: 25+ years old Sorry no pets

Top guest favorite
A multi-level house is set on a grassy area, featuring a stairway leading to a deck adorned with flower pots. Vibrant red canopies provide shade, and bicycles are stationed nearby, creating an inviting environment. The exterior showcases a mix of wooden and painted surfaces.
Home in Chesterton
4.82 out of 5 average rating, 345 reviews

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. ✌️

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, 223 reviews

Casa Gitana - Boutique Style Stay in Three Oaks

Casa Gitana is a Boutique style stay in the quaint town of Three Oaks, MI. Just a short drive to the pristine beaches of Lake Michigan and walking distance to downtown, our home offers an eclectic & contemporary feel that is perfect for a relaxing getaway any time of the year. We personally manage & oversee the home before every stay, & take pride in putting thought & intention into every detail. We want our guests to feel at home, and most importantly enjoy a comfortable and relaxing stay. :)

Superhost
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
4.84 out of 5 average rating, 109 reviews

Indiana Dunes, Beach, Chicago, Shopping Center

Near Indiana Dunes, Lake Michigan and Chicago when you stay at our centrally-located townhome. For family fun we’re is located a few minutes away from the shopping center, plenty of restaurants, main chain stores and more. Enjoy the convenience a parking garage& driveway, outdoor patio, dishwasher and washer & dryer. home has 4 beds 2 bedrooms. One bedroom has a Queen bed, second bedroom has a Queen bed and a Full bed. The Living room has a sofa bed. Shovel in the garage for when it snows.

Top guest favorite
A cabin exterior is presented, featuring a screened-in porch that offers comfortable seating. The structure, painted in a muted green tone, is surrounded by trees and foliage. A set of steps leads to the porch, creating easy access to the welcoming retreat.
Cabin in Union Pier
4.99 out of 5 average rating, 118 reviews

Walk 2 Lake/Shops | Hot Tub | King Bed | Fireplace

Tucked away sophisticated cabin in the heart of Downtown Union Pier. Killer location that's just steps away from dining and drinks: Black Current Bakery, Neon Moon Gelato, Union Pier Market, and Union Pier Social. Townline Beach is a 10 minute walk, and the cabin is right off the bike path. Seeds Brewery is just down the road and local Wineries are 1 mile away. Back home enjoy a relaxing hot tub (available year round), wood burning fire place, spacious screened in porch & outdoor fire pit.

Top guest favorite
Home in Michigan City
4.97 out of 5 average rating, 229 reviews

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. Explore all the south shore of Lake Michigan has to offer then kick back at your home away from home. Only a half mile walk to the Southshore commuter train to Chicago! So COZY. 💙

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
4.88 out of 5 average rating, 117 reviews

New Dunes Escape

Your family will be close to everything when you stay at this centrally-located place. Located just 3 minutes from the entrance of the Indiana Dunes National Park, 45 minutes from Chicago, 45 minutes from New Buffalo, MI , and 3 minutes from the Dunes Park South Shore Station, this completely remodeled home is the perfect place for a get-away. With free wifi, firepit with firewood, and a 4-seasons room, this house is the perfect place to relax after a great day swimming or hiking.

Guest favorite
A charming two-story home features light blue siding and white exterior accents. A welcoming front porch is bordered by a white picket fence. Large windows allow natural light to fill the space, offering a glimpse of the cozy seating area within.
Home in Michigan City
4.85 out of 5 average rating, 140 reviews

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.

Top guest favorite
The exterior of Chalet Valpo features a charming two-story white house with a pitched roof. The front porch is accessible with a gravel path, offering wooden steps and a small seating area with a table and chairs. A fenced yard provides additional privacy.
Guesthouse in Valparaiso
4.98 out of 5 average rating, 200 reviews

Cozy Luxe Downtown Valparaiso Stay

Welcome to “Chalet Valpo”! A historic carriage house located minutes from the heart of Valpo that we have had completely gutted and made new for you! This home is a carriage house, it is located on our personal property. You have complete privacy during your stay in a private fenced in area. Do not hesitate to reach out with any questions. Walkable to downtown Valparaiso! NO CLEANING FEE!

Superhost
The exterior of the house is shown with a deck that features white railings and steps leading down to a grassy area. Lush greenery surrounds the home, providing a secluded atmosphere. A large window on the right allows natural light into the interior.
Home in Chesterton
4.84 out of 5 average rating, 110 reviews

National Park Nature Lover's Retreat

Nestled on over a half acre and surrounded by Indiana Dunes National Park, our home offers panoramic views of the surrounding forestry. Secluded but only a mile from the South Shore train station with access to Chicago and the National Park Campground. Enjoy the large indoor and outdoor space with friends and family or explore all that the Indiana lake shore and Chicago has to offer.

Top guest favorite
The exterior of the home showcases a white siding and large windows, surrounded by lush greenery. A wooden deck with seating is visible, complemented by stone steps leading to the yard. The fenced area offers a private outdoor space for relaxation.
Cottage in Valparaiso
4.96 out of 5 average rating, 114 reviews

Cozy 2 Bedroom Valparaiso Cottage

This quiet, centrally located north side home offers a perfect place to relax. Only minutes away from downtown Valparaiso and the Indiana Dunes National Park. Conveniently situated for day and evening adventures and activities. Such as, local lakes, parks, and festivals. Enjoy hiking, bird watching, swimming, fishing, fine dining, local breweries and wineries, and so much more.

Popular amenities for Chesterton patio rentals

When is the best time to visit Chesterton?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ411ﺩ.ﺇ507ﺩ.ﺇ466ﺩ.ﺇ474ﺩ.ﺇ588ﺩ.ﺇ621ﺩ.ﺇ661ﺩ.ﺇ690ﺩ.ﺇ606ﺩ.ﺇ540ﺩ.ﺇ569ﺩ.ﺇ525
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Quick stats about vacation rentals with a patio in Chesterton

  • Total vacation rentals

    Explore 40 vacation rentals in Chesterton

  • Nightly prices starting at

    Chesterton vacation rentals start at ﺩ.ﺇ257 per night before taxes and fees

  • Verified guest reviews

    Over 4,400 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 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!