Holiday rentals in Chesterton

4.99 out of 5 average rating, 494 reviews

Farm stay in La Porte

Cabin on Swede Hill

Welcome to "Cabin on Swede Hill". Our family has farmed this land since 1871. My great grandparents, Swan and Johanna Johnson immigrated to America in the 1860's, found this land which was similar to Sweden. They raised their family here. Approximately 65 Swedish families settled in this community, became to be know as the "Swede Hills". We just received the Hoosier Homestead Award from Indiana celebrating the Sesquicentennial Award. We invite you to come...... and experience country life.

4.88 out of 5 average rating, 547 reviews

Cottage in Valparaiso

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 a that leads to Flint lLake.The lake can be acce - Pet free - 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 - Local breweries & award winning restaurants - Biking & hiking trails near by - Wood fire places to enjoy in cold weather only

4.8 out of 5 average rating, 297 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. ✌️

4.95 out of 5 average rating, 126 reviews

Flat in Michigan City

Heart of Historical Dist.*King*Parking*A/C*#1

Our charming one bedroom apartment is perfect for a getaway in Northwest IN and will provide everything you need to have an enjoyable stay! Located near Lighthouse Outlets, Restaurants, Casino, Breweries, Indiana Dunes National & State Parks (7 -11.3 miles), Washington Park (1.4 miles) and more! South Shore Line electric train platform is right behind property. (in quiet zone). Day trips are easy to downtown Chicago or South Bend IN. Catch a Notre Dame game one day and see the Bears the next.

4.9 out of 5 average rating, 126 reviews

Downtown Chesterton "Grant-Cottage"

Charming downtown house with a front porch, back deck & covered patio. Beautifully decorated with a small fenced in backyard. Minutes from the Indiana Dunes National Park and beaches. Near the South Shore Commuter train if you wish to visit Chicago without the drive and expense of parking. We are across from an active train track so if you like trains you can watch them from the front porch. Walk to restaurants, wineries and beer pubs. European market on Saturdays from May to end of October.

5 out of 5 average rating, 180 reviews

Barn in Valparaiso

The Good Farm: Barn BnB on 44 acres near Lake Mich

Enjoy 44 acres just 15 minutes from the beaches of Lake Michigan! With room to sleep 6, guests will enjoy this fully stocked barn apartment with gorgeous views! You'll be near Indiana Dunes National Park, tree-lined hiking/biking trails, wineries, cafes, outlet malls, & antique shops. Roast s'mores in the fire pit, watch chickens free range through the yard or grab a bite to eat downtown Valpo/Chesterton/MC—the perfect getaway for families or friends who want to relax or adventure in nature.

Guest house in Valparaiso

4.93 out of 5 average rating, 202 reviews

Private Cottage in Gated Nudist Community

We offer a private cottage on the grounds of Lake O the Woods Club. Cottage has Queen size bed, air conditioning, heater, refrigerator, microwave, TV, coffee maker, work/dining area, private deck and porta-potty. Payment of club daily grounds fee ($30-$60) is mandatory. Pricing on club website. There is no running water in the cottage. Bathrooms, showers, hot tub, sauna and swimming pool are available at the clubhouse and pool area . The cottage is sanitized after every rental.

Guest house in Chesterton

4.96 out of 5 average rating, 168 reviews

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

4.95 out of 5 average rating, 176 reviews

Cottage in Gary

Neon Dunes Vista Beachfront Cottage

Neon Dunes Cottage is perfect for a romantic getaway. A newly renovated cottage with new kitchen, modern appliances and new bathroom all in a bright airy home. It is located in Indiana Dunes National Park/Miller Beach. Only 1.5 blocks to the beach, you can hike trails nearby and come back to relax in a unique, comfortable setting with ambiance and charm. It's perfect for summer/holidays. Wifi, onsite parking and self check in, allow you to enjoy our wonderful home in privacy and peace.

Guest house in Chesterton

4.92 out of 5 average rating, 366 reviews

"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.

4.78 out of 5 average rating, 54 reviews

Loft in Chesterton

That 70’s Loft! Peace, Love & Poolside Vibes

Embrace the 70s vibe in our funky loft, where the inspiration is retro charm and modern comfort! And have an extra special stay knowing you have a private pool to relax in! This airbnb is perfect for: -Business trips -Family visits -Nature lovers seeking a small-town escape. Located within a 10-minute trip to the beach, walking distance of local hot spots, under an hour trip to the vibrant city of Chicago, Illinois, and less than 30 minutes from charming New Buffalo, Michigan.

4.97 out of 5 average rating, 180 reviews

Home in Michigan City

5 Min Drive Lake Michigan beach-brewery-casino-zoo

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!

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space that's all yours, with room for everyone

Hotels

Stylish accommodation and amenities

Popular amenities for Chesterton holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Chesterton

4.98 out of 5 average rating, 157 reviews

Hotel Whiskey

MallaryRating, 5 stars4 weeks ago

Cute little place right in downtown Chesterton. Very convenient: 5-minute drive to Dunes visitor center (and I-94), and 10 minutes to state park gate. There are a handful of restaurants and shops within easy walking distance. Quiet street, lovely screened-in porch and fenced backyard. Wifi worked well, drinks in the fridge upon arrival, comfortable bed and couch. Host proactively offered to install the window AC units the night before an unseasonably hot day (90-ish degrees in mid-May).

4.79 out of 5 average rating, 76 reviews

Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home

KieranRating, 5 stars1 month ago

Great house for the value! Clean and lots of amenities! Wish we visited in summer as fenced backyard is great! Stairs to second floor are steep but in good condition with handrail! There are local trains that are present throughout the day/night, but their sound didn’t bother us 😊 Overall a great value and lovely vintage home! Host was very responsive and friendly! Thank you!

4.98 out of 5 average rating, 40 reviews

Home in Porter

National Park / Lake Michigan Neighbor

SantosRating, 5 stars3 weeks ago

Perfect for our trip. We attended the Indiana Dunes Bird Festival. This place was perfectly located for all of our activities. Later this summer if we go up for a beach getaway we would stay again. Walkable to deep dish pizza too. Great host. Very responsive. Thanks for the great stay.

5 out of 5 average rating, 6 reviews

Home in Valparaiso

Downtown 2 BR Cottage w/ King Bed

JamieRating, 5 stars1 week ago

Hayley's place was beautifully remodel with cool upgrades. Easy 15 minute walk to restaurants and shops. I loved the kitchen. I was able to make amazing breakfasts and dinners for my family. Beds are so comfortable. We didn't want to leave. Hope to be back soon.

4.71 out of 5 average rating, 14 reviews

Charming Chesterton Home: w/ Idyllic Location!

ZackRating, 5 stars1 month ago

House was very clean upon arrival. Nicely decorated as well. Perfect for the weekend stay we needed! Fair warning - it is near train tracks, so you will hear trains. Didn’t bother us too much though!

4.85 out of 5 average rating, 211 reviews

Home in Porter

Modern Indiana Beach Home Near Lake Michigan

RachelRating, 5 stars2 weeks ago

We loved our stay at Jessica's place. The deck off the living room was the perfect place for relaxing with a cup of coffee or a glass of wine. It felt like we were in a tree house. Lots of great, natural lighting on the main floor. We loved the sky lights and the back yard is woodsy, lovely, and private. We really enjoyed having campfires and creating lots of memories in the peaceful environment. The dining room perfectly fit our group of seven for dinners and games. We would definitely come back again. Being minutes away from Indiana National Dunes Park and the State Park was a treasure.

4.95 out of 5 average rating, 37 reviews

Home in Michigan City

Lake Trail Cottage(NO Cleaning Fee!)

KatherineRating, 5 stars4 days ago

A great stay close to the Dunes! We took the South Shore Line into Chicago and did the 3 Dune Challenge and both were great. Highly recommend this place.