Vacation rentals in Chesterton

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Chesterton

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

Guest favorite

Home in Michigan City

4.94 out of 5 average rating, 399 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.

Jul 25 – Aug 1

G$30,574 GYD per night
Superhost

Apartment in Michigan City

4.87 out of 5 average rating, 137 reviews

Perfect 1 Bed Penthouse Steps To Beach w/Parking!

Looking to spend some time away from the chaos of life and stay in a beautifully updated home steps from a private beach on Lake Michigan? Welcome to Sheridan Beach in Michigan City! This perfect 1 bed/1 bath penthouse unit is situated within a block of the beach/water. The serenity of the neighborhood and seclusion from the outside world are its most attractive features. Located a little over an hour from Chicago, it's a quick drive to enjoy some R&R. Get ready to make some amazing memories.

Apr 12 – 19

G$24,715 GYD per night
Guest favorite

Farm stay in De Motte

4.94 out of 5 average rating, 109 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.

Jan 24 – 31

G$17,638 GYD per night

Popular amenities for Chesterton vacation rentals

Stay near Chesterton's top sights

Indiana Dunes National Lakeshore Visitor Center12 locals recommend
Wagner's Ribs19 locals recommend
Jewel-Osco12 locals recommend
Strack & Van Til7 locals recommend
Octave Grill18 locals recommend
Leroy's "Hot Stuff"4 locals recommend

Other great vacation rentals in Chesterton

Guest favorite

Guesthouse in New Buffalo

4.96 out of 5 average rating, 464 reviews

Rainbows End 🌈 Plensa

Sep 20 – 27

G$31,861 GYD per night
Superhost

Home in Porter

4.82 out of 5 average rating, 150 reviews

Modern Indiana Beach Home Near Lake Michigan

Jan 1 – 8

G$50,891 GYD per night
Guest favorite

Home in Portage

4.92 out of 5 average rating, 145 reviews

Newly Renovated with Finished Basement

Jan 27 – Feb 3

G$33,659 GYD per night
Guest favorite

Home in Chesterton

4.86 out of 5 average rating, 147 reviews

Sweet Home in Chesterton

Apr 2 – 9

G$36,586 GYD per night
Guest favorite

Guesthouse in Valparaiso

4.95 out of 5 average rating, 371 reviews

Private Guest House, in Gated Nudist Resort.

May 15 – 22

G$25,813 GYD per night
Guest favorite

Guesthouse in Porter

4.86 out of 5 average rating, 672 reviews

'Pool Barn' w/Games & Hot Tub near Indiana Dunes

Sep 9 – 16

G$69,494 GYD per night
Guest favorite

Home in Michigan City

4.92 out of 5 average rating, 205 reviews

✦Cozy Bungalow✦ Central location, 2.4mi to Beach

Oct 3 – 10

G$28,760 GYD per night
Guest favorite

Guesthouse in Plymouth

4.99 out of 5 average rating, 487 reviews

Sue's Place

Oct 20 – 27

G$18,148 GYD per night
Guest favorite

Home in Michigan City

4.96 out of 5 average rating, 207 reviews

The Little House In the Big Woods

May 12 – 19

G$36,048 GYD per night
Guest favorite

Cabin in Grovertown

4.92 out of 5 average rating, 197 reviews

Cozy Cabin at Coppertop Barn

Jul 29 – Aug 5

G$29,756 GYD per night
Guest favorite

Home in Michigan City

4.98 out of 5 average rating, 227 reviews

House of Zen: Peaceful Modern Cabin on Tryon Farm

Aug 18 – 25

G$40,200 GYD per night
Guest favorite

Cabin in Michigan City

4.95 out of 5 average rating, 392 reviews

Little Copper Cabin

Sep 14 – 21

G$39,678 GYD per night

Other great vacation rentals in Chesterton

Guest favorite

Home in Chesterton

4.94 out of 5 average rating, 35 reviews

The H'Art of Chesterton

Jan 13 – 20

G$35,965 GYD per night
Guest favorite

Cottage in Valparaiso

4.95 out of 5 average rating, 44 reviews

Cozy 2 Bedroom Valparaiso Cottage

Jun 12 – 19

G$23,644 GYD per night
Guest favorite

Home in Portage

4.82 out of 5 average rating, 17 reviews

Cozy Cottage Guest House

Apr 7 – 14

G$24,405 GYD per night
Guest favorite

Apartment in Valparaiso

4.81 out of 5 average rating, 58 reviews

Studio Apt. Near Downtown Valpo! (.2 mile walk)

Sep 8 – 15

G$21,418 GYD per night
Guest favorite

Home in Porter

5.0 out of 5 average rating, 29 reviews

Dunes Woodland

Nov 24 – Dec 1

G$39,290 GYD per night
Guest favorite

Condo in Portage

4.96 out of 5 average rating, 78 reviews

Cozy 1 bedroom condo on Marina near Lake Michigan

Oct 31 – Nov 7

G$30,977 GYD per night
Guest favorite

Home in Portage

5.0 out of 5 average rating, 29 reviews

Indiana Dunes, Beach, Chicago, Shopping Center

Apr 23 – 30

G$21,558 GYD per night
Guest favorite

Home in Porter

4.93 out of 5 average rating, 40 reviews

Brand New Dunes Escape

Nov 21 – 28

G$37,450 GYD per night
Superhost

Home in Chesterton

4.82 out of 5 average rating, 51 reviews

National Park Nature Lover's Paradise

May 23 – 30

G$39,176 GYD per night
Guest favorite

Home in Valparaiso

4.83 out of 5 average rating, 66 reviews

Cheerful three bedroom home in Downtown Valparaiso

Aug 4 – 11

G$27,557 GYD per night
Guest favorite

Cabin in Portage

4.97 out of 5 average rating, 72 reviews

Cozy Log Cabin Near Indiana Dunes & Lake Michigan!

Feb 23 – Mar 2

G$48,079 GYD per night
Guest favorite

Home in La Porte

4.95 out of 5 average rating, 21 reviews

Secluded 3-BR cottage w/ hot tub

Jan 10 – 17

G$22,653 GYD per night

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

3.2K reviews

Nightly prices starting at

G$2,094 GYD 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.

Destinations to explore

  1. Airbnb
  2. United States
  3. Indiana
  4. Porter County
  5. Chesterton