Vacation rentals in Chesterton

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Top-rated vacation rentals in Chesterton

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Guest favorite

Farm stay in La Porte

4.99 out of 5 average rating, 445 reviews

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.

Guest favorite

Home in Michigan City

4.97 out of 5 average rating, 233 reviews

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, 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 during our high season (mid May-mid September), and open 2 night stays 1-2 weeks prior if we have a couple open days.

Guest favorite

Cottage in Valparaiso

4.88 out of 5 average rating, 499 reviews

Flint Lake Cottage.

This is a rustic cottage with old world charm. There are 2 fireplaces,. The home sits on a hill overlooking a lake. The lake can be accessed from the back yard. - 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

Guest favorite

Villa in Michigan City

4.89 out of 5 average rating, 131 reviews

Steps from the beach. Entire beach villa renovated

Private, ~800 sq ft, ground-level renovated beach villa with close trail access to the beach. Includes 1 BR with queen bed, 1 BR with futon & extra folding guest bed, kitchen, bathroom, & living room with small couch that converts to sleeping space if needed. Amenities: washer/dryer, free wi-fi/streaming services, 2 free parking spaces, AC/heating, self check-in, laptop friendly workspace, games, complimentary coffee/tea, beach chairs, towels, umbrella & toys, & cleaning/laundry supplies.

Guest favorite

Barn in Michigan City

4.96 out of 5 average rating, 350 reviews

The Black Pearl Great Escape Spa & Art Shop

Check out our website! thegreatescapespah.com The Black 🖤 Pearl is perfect for a Special Occasion for the Evening. Book a Couples Massage @ 3p.m. & Check into your Spa Suite @ 4 p.m. Kick your feet Up & Order in.... Or Dine Out~ This quaint property is located in a woodsy setting 5 minutes from Lake Michigan. The keyless entry door to The Black Pearl is located on the East wall of The Great Escape. Upon entry the Black Pearl door will be directly in front of you. Mini Luxury awaits!

Guest favorite

Guesthouse in Chesterton

4.97 out of 5 average rating, 118 reviews

Bro’s Place

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

Guest favorite

Cottage in Gary

4.97 out of 5 average rating, 118 reviews

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 favorite

Guesthouse in New Buffalo

4.98 out of 5 average rating, 703 reviews

"Tiny House" Guest House Under the Oak Trees

"Tiny House" guest house located under large oak trees near the beach, and not far from I-94 and the Michigan state line. Vaulted ceiling, open feeling. Light and bright décor. Full bathroom, comfy couch, and other amenities. Polished concrete floor, whitewashed shiplap ceiling, hand-crafted oak furniture, suspended shelving. High ceilings, windows with southern exposure, front porch with siting chairs and a grill. Convenient charger for electric cars. Never a cleaning fee.

Guest favorite

Guesthouse in Chesterton

4.91 out of 5 average rating, 318 reviews

"myhathouse" detached studio downtown Chesterton

Vaulted skylights allow natural light. Ksize bed. Futon opens into a 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

Guest favorite

Guesthouse in Valparaiso

4.95 out of 5 average rating, 373 reviews

Private Guest House, in Gated Nudist Resort.

Book your get away today. Make it a few days or a week. If you've ever thought of trying social nudity. This is the place to do it. Very private 200+ acre property. You can also USE GUESTHOUSE AS BASE FOR SHORT DAY TRIPS, to Indiana Dunes State Park, Michigan Wine Country, or Chicago. You won't find a more beautiful, cost effective setting for a get away. This listing is for Guest house only (see guest access below)...where NUDITY IS NOT REQUIRED.

Guest favorite

Home in Chesterton

4.98 out of 5 average rating, 128 reviews

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.

Guest favorite

Cottage in Merrillville

4.89 out of 5 average rating, 189 reviews

The Hideaway

This cozy cottage (lodging only, renters only) located 30 minutes from Chicago is located on a private 3 acre property. It’s a private detached cottage that sleeps four. One king size bedroom (sheets supplied), large full bathroom with deep tub (towels supplied), full kitchen (dishes, pots and pans ect supplied) and private parking. Also has its own fire pit for enjoyment.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chesterton vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Chesterton's top sights

Jewel-Osco12 locals recommend

Indiana Dunes National Lakeshore Visitor Center12 locals recommend

Wagner's Ribs19 locals recommend

Octave Grill18 locals recommend

Strack & Van Til7 locals recommend

Leroy's "Hot Stuff"4 locals recommend

Other great vacation rentals in Chesterton

Guest favorite

Barn in Rensselaer

5.0 out of 5 average rating, 282 reviews

The Loft at Virgie

Guest favorite

Home in De Motte

4.95 out of 5 average rating, 212 reviews

Country Cottage

Guest favorite

Guest suite in Crown Point

4.93 out of 5 average rating, 209 reviews

IT'S THE WRIGHT PLACE

Guest favorite