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
Home in Porter
4.82 out of 5 average rating, 152 reviewsModern Indiana Beach Home Near Lake Michigan
Jan 19 – 26
Cottage in Merrillville
4.89 out of 5 average rating, 183 reviewsThe Hideaway
Jul 28 – Aug 4
Cabin in Michigan City
4.95 out of 5 average rating, 398 reviewsLittle Copper Cabin
Jan 28 – Feb 4
Camper/RV in Porter
4.79 out of 5 average rating, 606 reviews'Pool Barn Camper' w/Hot Tub near Indiana Dunes
Oct 6 – 13
Home in Chesterton
4.86 out of 5 average rating, 147 reviewsSweet Home in Chesterton
Apr 24 – May 1
Home in Portage
4.92 out of 5 average rating, 148 reviewsNewly Renovated with Finished Basement
Nov 4 – 11
Home in Chesterton
5.0 out of 5 average rating, 18 reviewsBeautiful Vintage house
Jan 9 – 16
Home in Chesterton
4.95 out of 5 average rating, 39 reviewsBlue Birdhouse by the Beach - No Cleaning Fee
Feb 1 – 8
Other great vacation rentals in Chesterton
Home in Porter
5.0 out of 5 average rating, 31 reviewsDunes Woodland
Jan 23 – 30
Home in Trail Creek
4.98 out of 5 average rating, 65 reviewsLeo Lodge
Dec 2 – 9
Cottage in Valparaiso
4.96 out of 5 average rating, 47 reviewsCozy 2 Bedroom Valparaiso Cottage
Jun 24 – Jul 1
Home in Chesterton
4.95 out of 5 average rating, 38 reviewsThe H'Art of Chesterton
Oct 16 – 23
Home in Valparaiso
4.89 out of 5 average rating, 9 reviewsSerene Settings
Jan 1 – 8
Home in Chesterton
4.83 out of 5 average rating, 54 reviewsNational Park Nature Lover's Paradise
Oct 1 – 8
Condo in Portage
5.0 out of 5 average rating, 53 reviewsLuxury Waterfront 2 Bedroom Condo by Lake Michigan
Sep 3 – 10
Home in Porter
4.9 out of 5 average rating, 41 reviewsThe Dune Den! Huge Yard/Firepit/Near Town+Dunes
Nov 14 – 21
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
€ 9 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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- Rentals with a washer and dryer Chesterton
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