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.
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 Valparaiso
4.95 out of 5 average rating, 371 reviewsPrivate Guest House, in Gated Nudist Resort.
Sep 18 – 25
Home in Chesterton
4.86 out of 5 average rating, 147 reviewsSweet Home in Chesterton
Apr 24 – May 1
Home in Porter
4.82 out of 5 average rating, 152 reviewsModern Indiana Beach Home Near Lake Michigan
Mar 27 – Apr 3
Home in Portage
4.92 out of 5 average rating, 148 reviewsNewly Renovated with Finished Basement
Feb 22 – Mar 1
Camper/RV in Porter
4.79 out of 5 average rating, 606 reviews'Pool Barn Camper' w/Hot Tub near Indiana Dunes
Dec 26 – Jan 2
Home in Valparaiso
5.0 out of 5 average rating, 112 reviewsLonely Pine Guest House: A Peaceful, Wooded Stay
Sep 19 – 26
Home in Chesterton
5.0 out of 5 average rating, 18 reviewsBeautiful Vintage house
Jan 8 – 15
Home in Valparaiso
4.96 out of 5 average rating, 85 reviewsCozy Luxe Downtown Valparaiso Stay
Aug 26 – Sep 2
Other great vacation rentals in Chesterton
Home in Valparaiso
4.89 out of 5 average rating, 9 reviewsSerene Settings
Aug 11 – 18
Cottage in Valparaiso
4.96 out of 5 average rating, 47 reviewsCozy 2 Bedroom Valparaiso Cottage
Jun 24 – Jul 1
Tiny home in Michigan City
4.97 out of 5 average rating, 76 reviewsThe Studio at the Dunes
Dec 8 – 15
Home in Chesterton
4.95 out of 5 average rating, 39 reviewsBlue Birdhouse by the Beach - No Cleaning Fee
Aug 27 – Sep 3
Home in Chesterton
4.95 out of 5 average rating, 38 reviewsThe H'Art of Chesterton
Oct 15 – 22
Home in Chesterton
4.83 out of 5 average rating, 54 reviewsNational Park Nature Lover's Paradise
Aug 23 – 30
Condo in Portage
5.0 out of 5 average rating, 53 reviewsLuxury Waterfront 2 Bedroom Condo by Lake Michigan
Sep 9 – 16
Cabin in Portage
4.97 out of 5 average rating, 74 reviewsCozy Log Cabin Near Indiana Dunes & Lake Michigan!
Feb 7 – 14
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
ﺩ.ﺇ37 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.
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