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.
Home in Michigan City
4.94 out of 5 average rating, 399 reviewsSmall 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
Apartment in Michigan City
4.87 out of 5 average rating, 137 reviewsPerfect 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
Farm stay in De Motte
4.94 out of 5 average rating, 109 reviewsCozy 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
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesterton vacation rentals
Other great vacation rentals in Chesterton
Guesthouse in New Buffalo
4.96 out of 5 average rating, 464 reviewsRainbows End 🌈 Plensa
Sep 20 – 27
Home in Porter
4.82 out of 5 average rating, 150 reviewsModern Indiana Beach Home Near Lake Michigan
Jan 1 – 8
Home in Portage
4.92 out of 5 average rating, 145 reviewsNewly Renovated with Finished Basement
Jan 27 – Feb 3
Home in Chesterton
4.86 out of 5 average rating, 147 reviewsSweet Home in Chesterton
Apr 2 – 9
Guesthouse in Valparaiso
4.95 out of 5 average rating, 371 reviewsPrivate Guest House, in Gated Nudist Resort.
May 15 – 22
Guesthouse in Porter
4.86 out of 5 average rating, 672 reviews'Pool Barn' w/Games & Hot Tub near Indiana Dunes
Sep 9 – 16
Home in Michigan City
4.92 out of 5 average rating, 205 reviews✦Cozy Bungalow✦ Central location, 2.4mi to Beach
Oct 3 – 10
Guesthouse in Plymouth
4.99 out of 5 average rating, 487 reviewsSue's Place
Oct 20 – 27
Home in Michigan City
4.96 out of 5 average rating, 207 reviewsThe Little House In the Big Woods
May 12 – 19
Cabin in Grovertown
4.92 out of 5 average rating, 197 reviewsCozy Cabin at Coppertop Barn
Jul 29 – Aug 5
Home in Michigan City
4.98 out of 5 average rating, 227 reviewsHouse of Zen: Peaceful Modern Cabin on Tryon Farm
Aug 18 – 25
Cabin in Michigan City
4.95 out of 5 average rating, 392 reviewsLittle Copper Cabin
Sep 14 – 21
Other great vacation rentals in Chesterton
Home in Chesterton
4.94 out of 5 average rating, 35 reviewsThe H'Art of Chesterton
Jan 13 – 20
Cottage in Valparaiso
4.95 out of 5 average rating, 44 reviewsCozy 2 Bedroom Valparaiso Cottage
Jun 12 – 19
Home in Portage
4.82 out of 5 average rating, 17 reviewsCozy Cottage Guest House
Apr 7 – 14
Apartment in Valparaiso
4.81 out of 5 average rating, 58 reviewsStudio Apt. Near Downtown Valpo! (.2 mile walk)
Sep 8 – 15
Home in Porter
5.0 out of 5 average rating, 29 reviewsDunes Woodland
Nov 24 – Dec 1
Condo in Portage
4.96 out of 5 average rating, 78 reviewsCozy 1 bedroom condo on Marina near Lake Michigan
Oct 31 – Nov 7
Home in Portage
5.0 out of 5 average rating, 29 reviewsIndiana Dunes, Beach, Chicago, Shopping Center
Apr 23 – 30
Home in Porter
4.93 out of 5 average rating, 40 reviewsBrand New Dunes Escape
Nov 21 – 28
Home in Chesterton
4.82 out of 5 average rating, 51 reviewsNational Park Nature Lover's Paradise
May 23 – 30
Home in Valparaiso
4.83 out of 5 average rating, 66 reviewsCheerful three bedroom home in Downtown Valparaiso
Aug 4 – 11
Cabin in Portage
4.97 out of 5 average rating, 72 reviewsCozy Log Cabin Near Indiana Dunes & Lake Michigan!
Feb 23 – Mar 2
Home in La Porte
4.95 out of 5 average rating, 21 reviewsSecluded 3-BR cottage w/ hot tub
Jan 10 – 17
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
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