Holiday rentals with a patio in Chesterton

Find and book unique rentals with patio on Airbnb

Top-rated rentals with patio in Chesterton

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

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Guest favourite
Home in Michigan City
4.97 out of 5 average rating, 254 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. 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. 💙

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
4.92 out of 5 average rating, 132 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

Guest favourite
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, 365 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 favourite
Home in Three Oaks
4.97 out of 5 average rating, 239 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, 118 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 favourite
A stylish living area features a blue sofa with throw pillows, situated on a patterned rug. Natural light streams through a skylight, illuminating the open layout that includes a dining space and kitchen with modern appliances. Minimalist decor enhances the inviting ambiance.
Home in New Buffalo
4.95 out of 5 average rating, 204 reviews

Steps to Beach & Starbucks! Private Yard, Firepit!

Walk to Starbucks! Walk to beach, cafes, shops, ice cream, grocery! 2 queen bed 2 bath home is perfect to enjoy fenced yard, grill, fire pit, & yard games! Take a few days to explore wineries/breweries, art galleries, antique stores, kayaking, casino and more! Live bands Fridays/Saturdays till around 2am Memorial Weekend to Fall, New Year's at Casey's (behind property). Noise machines in each bdrm. Pet fee $100, 2 dogs MAX. Exterior areas have video/audio cameras w/live feeds. Wp#bcnbwmech

Guest favourite
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, 121 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 favourite
A spacious living area is highlighted by wooden beams and natural light. A comfortable sofa and armchairs arrange around a round coffee table. A striking wall art piece features a deer, while large glass doors provide views of the outdoors.
Cottage in Sawyer
4.97 out of 5 average rating, 170 reviews

Hot tub open year round in modern/rustic cottage!

Kick back and relax in this rustic & stylish cottage that is surrounded by gorgeous landscaping on almost 2 acres in Harbert. Cherry Beach a 5 min drive, 15 mins to New Buffalo, & minutes to Greenbush, Infusco, Susan's & the new Out There wine bar! Perfect place if you seek peace & quiet - play a record, hit the hot tub, read a book in screened in porch or hammock, hang out by the firepit or jump on one of the 4 bikes! So close to boutiques, coffee shops and cute restaurants!

Guest favourite
A bright living room is showcased, featuring a comfortable seating arrangement with a sofa and armchair. Natural light enters through large windows, illuminating the wood-tone flooring. A ceiling fan and framed wall art add to the welcoming ambiance.
Home in Porter
4.88 out of 5 average rating, 109 reviews

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!

Top guest favourite
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.
Guest house in Valparaiso
4.98 out of 5 average rating, 216 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 favourite
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
4.97 out of 5 average rating, 120 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 rentals with patio in Chesterton

When is the best time to visit Chesterton?

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Avg. price$141 SGD$174 SGD$160 SGD$163 SGD$202 SGD$213 SGD$231 SGD$245 SGD$201 SGD$185 SGD$196 SGD$180 SGD
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Quick stats about holiday rentals with a patio in Chesterton

  • Total holiday rentals

    Explore 40 holiday rentals in Chesterton

  • Nightly prices starting at

    Chesterton holiday rentals start at $76 SGD per night before taxes and fees

  • Verified guest reviews

    Over 4,510 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Chesterton holiday rentals include wifi 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!