Vacation rentals with outdoor seating in Chesterton

4.97 out of 5 average rating, 254 reviews

Home in Michigan City

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. 💙

Tiny home in Michigan City

The exterior of a red tiny house is framed by greenery, showcasing a wooden deck with railing. A hot tub is positioned on the deck, while a door and windows illuminate the structure, providing a welcoming atmosphere in a private yard.

4.99 out of 5 average rating, 221 reviews

The Studio at the Dunes

Experience tiny living at the Studio after a day exploring the beautiful Indiana Dunes National Park! You will love this cozy tiny house with vaulted ceilings and modern amenities. Cool off with the mini-split air conditioner and relax on the sofa chaise after a long day in the sun. Staying in? Enjoy a board game while listening to some oldies on the record player, take a dip in the cozy hot tub, or relax in the hammocks by the fire pit in the secluded back yard. You’re sure to leave refreshed!

4.91 out of 5 average rating, 114 reviews

A sandy pathway winds through tall grasses, leading to Lake Michigan. The tranquil water reflects the soft hues of the sky, with clouds adding texture to the serene scene. The beach's inviting atmosphere creates a perfect setting for relaxation and exploration.

Home in Porter

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! 🌞🏖️🌳

4.92 out of 5 average rating, 132 reviews

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

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

4.98 out of 5 average rating, 321 reviews

A spacious living area showcases a light-colored sectional sofa adorned with plush pillows. Large windows allow natural light to fill the room, revealing wooden flooring and eye-catching artwork on the walls. A dining table is visible in the background, complemented by a minimalist plant.

Home in Michigan City

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.

4.82 out of 5 average rating, 365 reviews

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

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. ✌️

4.98 out of 5 average rating, 123 reviews

A welcoming living area is brightened by natural light streaming through a large window. A comfortable gray daybed is adorned with decorative pillows, complemented by a cozy blue couch. A round coffee table sits on a textured rug, with a potted orchid as a centerpiece.

Apartment in Valparaiso

Cozy Casa: Downtown Digs!

Located in the heart of downtown Valparaiso, guests will love this updated, historic charmer! Walk to fabulous restaurants, local shops, or breweries & wineries in minutes. This unit has been fully updated and fully stocked with room to sleep 6. You'll be 25 minutes from the beaches of Lake Michigan/Indiana Dunes National Park, an hour from Chicago, and close to quaint towns and apple/berry picking orchards. This space is perfect for families & friends who want to relax or adventure outdoors!

4.96 out of 5 average rating, 194 reviews

Guesthouse in Chesterton

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

4.91 out of 5 average rating, 394 reviews

An outdoor space is presented with a patio featuring a round table and four chairs under a red umbrella. A fire pit is positioned nearby, with a pile of branches placed in the foreground. The area is enclosed by a wooden fence with decorative artwork visible.

Guesthouse in Chesterton

"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.

4.91 out of 5 average rating, 237 reviews

The front exterior of a single-story home is presented, featuring a light grey facade with white shutters. A welcoming porch is visible, adorned with vibrant plants. The property is surrounded by lush greenery, with trees providing natural shade in the background.

Home in Michigan City

Casinos, Shopping, Pets, and Parking a Plenty!

1 mile from BLUE CHIP CASINO - with its new SPORTS BOOK and is where the away team stays for NOTRE DAME FOOTBALL, 2 miles from the outlet mall, 7 blocks to the beach, and plenty of parking! 3 bedrooms (4 beds) and 1 bathroom. This is a great place regardless of the season and though in the city; it backs up to woods with lovely walking trails. The home also has hi speed internet/WiFi and HD cable television. Simple, practical home in a safe neighborhood - and it’s a bargain!

4.86 out of 5 average rating, 129 reviews

A compact kitchen area displays modern appliances, including a black refrigerator and a microwave. A wooden dining table with four chairs is positioned in the center. Open shelving above the counter features decorative items and kitchen essentials, complemented by a window allowing natural light.

Apartment in Valparaiso

Cute Skylar: Valparaiso University ShortTerm

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! ☺️

Guest suite in Crown Point

The exterior of a private guest house is shown, featuring a detached two-story structure. A driveway leads to a garage with a white door, while a wooden staircase ascends to the entryway. The surrounding area includes greenery and paved walkways.

4.94 out of 5 average rating, 261 reviews

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.

Popular amenities for Chesterton outdoor seating rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.84 out of 5 average rating, 110 reviews

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

National Park Nature Lover's Retreat

4.96 out of 5 average rating, 272 reviews

A modern kitchen is visible, featuring white cabinetry and stainless steel appliances. The living area includes a comfortable couch and a round table with a decorative runner. Natural light fills the space, highlighting the open layout and ceiling beams.

Home in Lakeside

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

4.96 out of 5 average rating, 229 reviews

The open living area features large floor-to-ceiling windows framing views of the surrounding woods. A sleek two-tone sofa and modern armchairs are arranged near a minimal table. Warm wooden flooring complements the contemporary design, and a staircase leads to the upper level.

Home in Beverly Shores

Secluded Modern Retreat Near Beach - "Sandlot"

4.9 out of 5 average rating, 250 reviews

An open living space showcases a blend of modern and rustic design elements. A spacious kitchen features stainless steel appliances, with bar stools positioned at the counter. Natural light filters in through large windows, illuminating the polished hardwood floors.

Home in Union Pier

CASA TICA Serenity Amongst Nature Dog Friendly

4.95 out of 5 average rating, 248 reviews

A welcoming living area is presented, featuring a light grey sectional sofa paired with plush armchairs. A dark coffee table sits at the center, complemented by a textured area rug. Natural light filters through the nearby window, adding warmth to the space.

Home in Portage

Newly Renovated with Finished Basement

5 out of 5 average rating, 141 reviews

A bright living area features a comfortable gray sofa adorned with decorative pillows, paired with a light brown armchair. Large windows provide views of lush greenery, while a striped rug anchors the space. A coffee table with a bowl sits at the center, enhancing the cozy atmosphere.

Home in Sawyer

The treehouse at Warren Dunes

4.97 out of 5 average rating, 101 reviews

Home in Buchanan

-The District 5 Schoolhouse-

4.99 out of 5 average rating, 132 reviews

The image displays a stylish living room featuring light-colored walls and a geometric area rug. A modern light fixture hangs above a rectangular coffee table, complemented by two leather chairs. The exterior view showcases a two-story home with a welcoming front porch and a blended color scheme.

Home in Three Oaks

2 blocks to Journeyman, 12 mins to Beach, King Bed

Apartment rentals with outdoor seating

4.85 out of 5 average rating, 170 reviews

A well-appointed bedroom features a spacious bed adorned with a soft blush and white blanket. A bedside lamp and decorative elements are present. Natural light filters through a window dressed with sheer curtains, creating a cozy ambiance. A small chair complements the interior design.

Apartment in Hammond

1Plant MOOD FREE Wi-Fi Parking Washer/Dryer

4.81 out of 5 average rating, 118 reviews

A spacious living room is filled with natural light from a large window. A comfortable gray sofa, red armchair, and black accent chair are arranged around a glass coffee table. A fireplace is set against an attractive wall, and a television is mounted above it.

Apartment in Bridgman

Relax - SW Mi Getaway/Hot Tub-Beaches & Wine Tours

4.97 out of 5 average rating, 205 reviews

A minimalist corner of the suite features a black sofa against a light-colored wall. Natural light streams in from a nearby window, adorned with sheer curtains. An artwork depicting floral designs is displayed on the wall, adding a subtle decorative touch to the space.

Apartment in Bridgman

Beachcomber Suite - Beaches, Dunes, Golf, Wine Tr

Apartment in Michigan City

The living area is furnished with a comfortable sofa, two chairs, and a coffee table, all arranged on soft, plush carpet. Natural light enters through two windows, and ceiling fans provide airflow. A doorway leads to another room, and curtains frame the windows.

4.88 out of 5 average rating, 8 reviews

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

Apartment in Near West Side

The open concept kitchen is equipped with modern appliances and features dark cabinetry. A dining table with four chairs is positioned near the kitchen. A cozy seating area with a gray sofa is visible in the background, complemented by soft lighting and a warm area rug.

4.9 out of 5 average rating, 115 reviews

Historic Studebaker Carriage House- Lower Level

4.89 out of 5 average rating, 120 reviews

Two white Adirondack chairs are positioned adjacent to a circular fire pit. The ground is covered with colorful fallen leaves, and trees with yellow foliage provide a natural backdrop. The scene reflects a serene outdoor space ideal for relaxation.

Apartment in Sawyer

Morton's Retreat Cozy 1 Bedroom Apartment

4.93 out of 5 average rating, 516 reviews

A circular stone fire pit is situated on a stone patio overlooking the lake. Flames flicker from the center, providing a warm glow against the twilight sky. The serene water reflects the evening colors, creating a peaceful waterfront setting.

Apartment in La Porte

Second Floor Apartment sitting on Pine Lake

4.93 out of 5 average rating, 384 reviews

Apartment in Sawyer

Cozy Mid-Century Mod By Lake MI&Dunes with Hot Tub

Condo rentals with outdoor seating

4.95 out of 5 average rating, 59 reviews

A light-filled living area features a cozy sofa facing a rustic wooden coffee table. The wall behind is adorned with nautical-themed decor, including an anchor and oars, complemented by blue cabinetry in the kitchen area.

Condo in Bridgman

Lakeside Serenity: One-Bedroom Villa

A cozy living area features a gray sofa adorned with decorative pillows, positioned near a window with light filtering through sheer curtains. A dark coffee table sits at the center, accompanied by a remote and a paper. A modern floor lamp stands nearby.

4.86 out of 5 average rating, 114 reviews

Updated Cottage Downtown, walk to Beach

Condo in Michigan City

4.74 out of 5 average rating, 57 reviews

MTM Premier Properties-on acres of tranquility

An outdoor pool is surrounded by lounge chairs, providing a relaxing area for guests. The three-story building features balconies on the upper floors. Clear blue skies add to the inviting atmosphere, enhancing the setting for relaxation and leisure.

5 out of 5 average rating, 5 reviews

2026 Open Perfect Location Condo Pools Walk to all

A modern living room features a comfortable gray sofa adorned with decorative pillows. A wooden coffee table sits in front of the sofa, while two lamps provide soft lighting. Artwork adorns the wall above, accompanied by a round mirror reflecting the space.

4.94 out of 5 average rating, 94 reviews

Nightingale Dunes - Modern beach town retreat

An aerial view showcases a marina filled with boats, adjacent to modern waterfront homes. The calm water reflects a clear sky, while a tree-lined pathway and parking area are visible in the foreground, enhancing the serene environment.

4.93 out of 5 average rating, 80 reviews

Live the marina life in New Buffalo!

A white lighthouse with red stripes stands on sandy beach land. The sky is filled with dramatic clouds, and the sun is setting on the horizon, casting warm hues in the sky. The surrounding area appears tranquil, enhancing the seaside atmosphere.

4.75 out of 5 average rating, 191 reviews

Lake Condo in the heart of Downtown New Buffalo