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Vacation rentals in Chesterton

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Top-rated vacation rentals in Chesterton

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

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Home in Chesterton

4.8 out of 5 average rating, 259 reviews

South Shore Studio Apartment {National Park}

I have to warn u 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 11 -8 generely some music playing and musicians are welcome !! if you happen to book on a sunday i host open mic in my Barn every sunday ..... pretty relaxed. Upon arriving turn into the driveway just passed my house and then right into the yard apartment is upstairs the door is open keys inside. ✌️

Home in Michigan City

4.94 out of 5 average rating, 432 reviews

Small Clean Home Near Beach, Casino, Outlet Mall

This cozy, clean home is located 2.9 miles to Beach, Outlet Mall, and Casino. Quiet neighborhood. Well maintained property. Perfect for a couple or business traveler. It is not child proof. It is not suitable for small children. There are open stairs that cannot be blocked. We do not accept pets. I have an autoimmune disease. I am allergic to pet dander We request drivers license of each guest f Per Airbnb guidelines I am disclosing we have cameras on exterior north/east of home with audio

Home in Portage

4.94 out of 5 average rating, 187 reviews

Newly Renovated with Finished Basement

This beautiful house is located near Lake Michigan in Northwest Indiana, less than 10 minutes from the expressway and toll road. There is a stainless steel kitchen, spa bathroom, finished basement and bar with sleeping capacity to accommodate two families. This is a smart home with Ring db, lights and thermostat controlled by your voice. We are less than an hour drive from downtown Chicago, and there are many great beaches nearby. Shopping and great dining options are also within a close drive.

Camper/RV in Porter

4.9 out of 5 average rating, 642 reviews

'Pool Barn Camper' w/Hot Tub near Indiana Dunes

Pool is open! Hot tub open all year! Fully equipped RV is parked in the driveway of our Pool Barn. RV sleeps 5, has bath w/shower, stove, microwave, heat & A/C, & running water all year. We are located minutes from the sand beaches of Indiana Dunes on Lake Michigan. Hiking in the Indiana Dunes National Park along the Little Calumet River and the historic Bailley homestead is only 1 block away. You may also use our large pool, hot tub, grill, campfire, and playground area. No cleaning fee!

Tiny home in Michigan City

4.98 out of 5 average rating, 132 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 NEW hot tub, or relax on the hammocks by the fire pit in the secluded back yard. You’re sure to leave refreshed!

Home in Chesterton

4.9 out of 5 average rating, 114 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.

Cottage in Valparaiso

4.88 out of 5 average rating, 533 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

Barn in Michigan City

4.97 out of 5 average rating, 407 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!

Condo in Portage

4.94 out of 5 average rating, 116 reviews

Cozy 1 bedroom condo on Marina near Lake Michigan

Come stay at this adorable one bedroom condo on the Marina near Lake Michigan! This condo has everything you need to enjoy a special getaway from everyday life. Conveniently located near the Indiana Dunes with the South Shoreline to Chicago directly across the street. Relax on the patio and enjoy watching the boats come and go as they please. Check out the drinks and food at the Marina Shores Yacht Club just a short walk away from this unit. This condo has everything you're looking for!

Guesthouse in Chesterton

4.96 out of 5 average rating, 154 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

Home in Michigan City

4.92 out of 5 average rating, 225 reviews

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!

Guesthouse in Chesterton

4.92 out of 5 average rating, 345 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

Vacation rentals for every style

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Cabins

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Popular amenities for Chesterton vacation rentals

Laptop-friendly workspace

Stay near Chesterton's top sights

Chesterton’s European Market20 locals recommend

Lucrezia® Café20 locals recommend

Wagner's Ribs19 locals recommend

Running Vines Winery18 locals recommend

Octave Grill18 locals recommend

Indiana Dunes National Lakeshore Visitor Center12 locals recommend

Other great vacation rentals in Chesterton

Home in Michigan City

4.79 out of 5 average rating, 47 reviews

The Lake Escape - 5 Mins from beach, casino, & zoo

Home in Michigan City

4.99 out of 5 average rating, 96 reviews

5 min to beach-zoo-brewery-casino-restaurants

Home in Portage

4.96 out of 5 average rating, 52 reviews

The Lake Place

Home in Valparaiso

4.92 out of 5 average rating, 51 reviews

Wooded Lake Home, 15 min. IN Dunes, 7=DT, 50=CHI.

Rental unit in Michigan City

4.99 out of 5 average rating, 80 reviews

Fresh 1 bedroom apartment downtown Michigan City

Home in Porter

4.92 out of 5 average rating, 60 reviews

The Dune Den! Huge Yard/Firepit/Near Town+Dunes

Cabin in Portage

4.95 out of 5 average rating, 94 reviews

Cozy Log Cabin Near Indiana Dunes & Lake Michigan!

Home in Michigan City

5 out of 5 average rating, 30 reviews

Superb Deal! 2 Miles from Beach

Quick stats about vacation rentals in Chesterton

Total rentals
60 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
4.2K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Chesterton?
Yes! Work meets play with ease at over 30 vacation rentals in Chesterton featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Chesterton?
Four-legged friends are welcome in Chesterton. Choose from more than 20 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Chesterton?
Experience the best of Chesterton with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Chesterton have wifi?
Absolutely! We offer over 40 house rentals with wifi in Chesterton. Enjoy a tailored experience with all the comforts you desire.

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