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

Farm stay in La Porte

4.99 out of 5 average rating, 441 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.

Jun 1 – 8

R2,647 ZAR per night

Guest favorite

Home in Michigan City

4.94 out of 5 average rating, 401 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.

Sep 16 – 23

R2,128 ZAR per night

Guest favorite

Home in Michigan City

4.96 out of 5 average rating, 216 reviews

Cozy House near Beach, Casino, Outlets, & Hiking

Escape with family or friends near the dunes of Lake Michigan! Recently renovated and decorated, you won't find a better rental! Guests will love this cozy home located near a variety of attractions. Just 2 miles from the sandy beaches, near tree-lined hiking trails in the nation's newest national park, casino, wineries, boat rentals, cafes, Michigan City Zoo, splash pad and park, outlet malls, & antique shops. This is the perfect little getaway for up to 6 people who want to relax or adventure!

Feb 18 – 25

R2,515 ZAR per night

Guest favorite

Cottage in Valparaiso

4.88 out of 5 average rating, 496 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

Sep 11 – 18

R2,464 ZAR per night

Guest favorite

Barn in Michigan City

4.96 out of 5 average rating, 343 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!

Sep 30 – Oct 7

R2,387 ZAR per night

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.

Dec 15 – 22

R2,586 ZAR per night

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

Nov 12 – 19

R1,981 ZAR per night

Guest favorite

Guesthouse in New Buffalo

4.98 out of 5 average rating, 695 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.

May 21 – 28

R2,597 ZAR per night

Guest favorite

Guesthouse in Chesterton

4.91 out of 5 average rating, 314 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

Feb 18 – 25

R1,942 ZAR per night

Guest favorite

Guesthouse in New Buffalo

4.96 out of 5 average rating, 471 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!

Mar 6 – 13

R2,784 ZAR per night

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.

Apr 14 – 21

R2,214 ZAR per night

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.

Feb 5 – 12

R3,446 ZAR per night

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

Farm stay in De Motte

4.94 out of 5 average rating, 113 reviews

Cozy barn loft on organic vegetable farm

Apr 4 – 11

R1,623 ZAR per night

Guest favorite

Home in Portage

4.92 out of 5 average rating, 149 reviews

Newly Renovated with Finished Basement

Feb 18 – 25

R3,092 ZAR per night

Guest favorite

Home in De Motte

4.96 out of 5 average rating, 207 reviews

Country Cottage

Nov 11 – 18

R2,090 ZAR per night

Guest favorite

Home in Valparaiso

5.0 out of 5 average rating, 112 reviews

Lonely Pine Guest House: A Peaceful, Wooded Stay

Sep 3 – 10

R3,966 ZAR per night

Guest favorite

Home in Michigan City

4.98 out of 5 average rating, 229 reviews

House of Zen: Peaceful Modern Cabin on Tryon Farm

Sep 3 – 10

R3,765 ZAR per night

Guest favorite

Cabin in Michigan City

4.96 out of 5 average rating, 210 reviews

The Little House at Tryon Farm

Sep 27 – Oct 4

R3,311 ZAR per night

Guest favorite

Guesthouse in Valparaiso

4.96 out of 5 average rating, 161 reviews

Private Cottage in Gated Nudist Community

Sep 30 – Oct 7

R1,213 ZAR per night

Superhost

Apartment in Valparaiso

4.85 out of 5 average rating, 112 reviews

Charming: Cute 2-bedrooms Valpo University

Apr 4 – 11

R2,151 ZAR per night

Show all

Other great vacation rentals in Chesterton

Guest favorite

Condo in Portage

4.96 out of 5 average rating, 78 reviews

Cozy 1 bedroom condo on Marina near Lake Michigan

Mar 3 – 10

R2,498 ZAR per night

Guest favorite

Home in Trail Creek

4.99 out of 5 average rating, 68 reviews

Leo Lodge

Feb 7 – 14

R1,985 ZAR per night

Guest favorite

Cottage in Valparaiso

4.96 out of 5 average rating, 49 reviews

Cozy 2 Bedroom Valparaiso Cottage

Jul 16 – 23

R2,423 ZAR per night

Guest favorite

Tiny home in Michigan City

4.97 out of 5 average rating, 76 reviews

The Studio at the Dunes

Feb 24 – Mar 3

R2,634 ZAR per night

Guest favorite

Home in Porter

4.93 out of 5 average rating, 43 reviews

Brand New Dunes Escape

Mar 28 – Apr 4

R3,338 ZAR per night

Guest favorite

Home in Porter

5.0 out of 5 average rating, 31 reviews

Dunes Woodland

Oct 6 – 13

R4,236 ZAR per night

Guest favorite

Condo in Portage

5.0 out of 5 average rating, 53 reviews

Luxury Waterfront 2 Bedroom Condo by Lake Michigan

Sep 15 – 22

R3,696 ZAR per night

Guest favorite

Home in Chesterton

4.95 out of 5 average rating, 38 reviews

The H'Art of Chesterton

Oct 23 – 30

R3,741 ZAR per night

Show all

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
R192 ZAR 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

Houses

Cabins

Hotels

Popular amenities for Chesterton vacation rentals

Stay near Chesterton's top sights

Other great vacation rentals in Chesterton

Farm stay in De Motte

Home in Portage

Home in De Motte

Home in Valparaiso

Home in Michigan City

Cabin in Michigan City

Guesthouse in Valparaiso

Apartment in Valparaiso

Other great vacation rentals in Chesterton

Condo in Portage

Home in Trail Creek

Cottage in Valparaiso

Tiny home in Michigan City

Home in Porter

Home in Porter

Condo in Portage

Home in Chesterton

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