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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Guest favorite

Home in Michigan City

4.94 out of 5 average rating, 400 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. Per Airbnb guidelines I am disclosing we have cameras on exterior north/east of home with audio.

Guest favorite

Farm stay in De Motte

4.94 out of 5 average rating, 113 reviews

Cozy barn loft on organic vegetable farm

Find peace and restoration in this beautiful barn loft at Perkins' Good Earth Farm. The loft has a bedroom, separate shower and toilet spaces, work area, sitting room, kitchen space, and heating/cooling fresh air system. Located above our farm store, the loft provides privacy for you while giving you access to fresh fruits & veggies, locally sourced meats, homemade soups & salads from our farm kitchen, and so much more. You can also walk our farm trails, visit the veggies, or enjoy a campfire.

Guest favorite

Cottage in Valparaiso

4.88 out of 5 average rating, 495 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

Barn in Michigan City

4.96 out of 5 average rating, 342 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

Villa in Michigan City

4.9 out of 5 average rating, 127 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

Guesthouse in Chesterton

4.96 out of 5 average rating, 114 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

4.96 out of 5 average rating, 113 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, 692 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, 313 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 New Buffalo

4.96 out of 5 average rating, 470 reviews

Rainbows End 🌈 Plensa

Escape to a tranquil countryside cottage on a 20-acre farm. Enjoy breathtaking sunrises from the picture window, relax in lounge chairs, and gather around the fire pit and grill or take a trail walk down to the south branch of the Galien River. Just 10 minutes from Lake Michigan, and within 5 miles of a casino and a golf course, it's the perfect retreat for nature lovers and entertainment seekers. Book now and experience rural bliss with nearby attractions!

Guest favorite

Guesthouse in Valparaiso

4.95 out of 5 average rating, 371 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, 125 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.

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

Superhost

Home in Porter

4.82 out of 5 average rating, 152 reviews

Modern Indiana Beach Home Near Lake Michigan

Guest favorite

Cottage in Merrillville

4.89 out of 5 average rating, 183 reviews

The Hideaway

Guest favorite

Cabin in Michigan City

4.95 out of 5 average rating, 398 reviews

Little Copper Cabin

Superhost

Camper/RV in Porter

4.79 out of 5 average rating, 606 reviews

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

Guest favorite

Home in Chesterton

4.86 out of 5 average rating, 147 reviews

Sweet Home in Chesterton

Guest favorite

Home in Portage

4.92 out of 5 average rating, 148 reviews

Newly Renovated with Finished Basement

Guest favorite

Home in Chesterton

5.0 out of 5 average rating, 18 reviews

Beautiful Vintage house

Guest favorite

Home in Chesterton

4.95 out of 5 average rating, 39 reviews

Blue Birdhouse by the Beach - No Cleaning Fee

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Other great vacation rentals in Chesterton

Guest favorite

Home in Porter

5.0 out of 5 average rating, 31 reviews

Dunes Woodland

Guest favorite

Home in Trail Creek

4.98 out of 5 average rating, 65 reviews

Leo Lodge

Guest favorite

Cottage in Valparaiso

4.96 out of 5 average rating, 47 reviews

Cozy 2 Bedroom Valparaiso Cottage

Guest favorite

Home in Chesterton

4.95 out of 5 average rating, 38 reviews

The H'Art of Chesterton

Guest favorite

Home in Valparaiso

4.89 out of 5 average rating, 9 reviews

Serene Settings

Guest favorite

Home in Chesterton

4.83 out of 5 average rating, 54 reviews

National Park Nature Lover's Paradise

Guest favorite

Condo in Portage

5.0 out of 5 average rating, 53 reviews

Luxury Waterfront 2 Bedroom Condo by Lake Michigan

Guest favorite

Home in Porter

4.9 out of 5 average rating, 41 reviews

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

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Quick stats about vacation rentals in Chesterton

Total rentals
50 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
3.4K reviews
Nightly prices starting at
$10 before taxes and fees

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 $40 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 30 house rentals with wifi in Chesterton. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Chesterton

Top-rated vacation rentals in Chesterton

Vacation rentals for every style

Cabins

Houses

Hotels

Popular amenities for Chesterton vacation rentals

Stay near Chesterton's top sights

Other great vacation rentals in Chesterton

Home in Porter

Cottage in Merrillville

Cabin in Michigan City

Camper/RV in Porter

Home in Chesterton

Home in Portage

Home in Chesterton

Home in Chesterton

Other great vacation rentals in Chesterton

Home in Porter

Home in Trail Creek

Cottage in Valparaiso

Home in Chesterton

Home in Valparaiso

Home in Chesterton

Condo in Portage

Home in Porter

Quick stats about vacation rentals in Chesterton

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Chesterton?

Are there pet-friendly vacation rentals in Chesterton?

How much does it cost to stay in house rentals in Chesterton?

Do house rentals in Chesterton have wifi?

Destinations to explore