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 Portage
4.92 out of 5 average rating, 149 reviewsNewly Renovated with Finished Basement
Feb 18 – 25
Home in Valparaiso
5.0 out of 5 average rating, 112 reviewsLonely Pine Guest House: A Peaceful, Wooded Stay
Sep 3 – 10
Home in De Motte
4.96 out of 5 average rating, 207 reviewsCountry Cottage
Nov 11 – 18
Home in Michigan City
4.98 out of 5 average rating, 229 reviewsHouse of Zen: Peaceful Modern Cabin on Tryon Farm
Sep 3 – 10
Cabin in Michigan City
4.96 out of 5 average rating, 210 reviewsThe Little House at Tryon Farm
Sep 27 – Oct 4
Guesthouse in Valparaiso
4.96 out of 5 average rating, 161 reviewsPrivate Cottage in Gated Nudist Community
Sep 30 – Oct 7
Apartment in Valparaiso
4.85 out of 5 average rating, 112 reviewsCharming: Cute 2-bedrooms Valpo University
Apr 4 – 11
Home in Chesterton
4.88 out of 5 average rating, 41 reviewsDunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home
Jan 24 – 31
Other great vacation rentals in Chesterton
Cottage in Valparaiso
4.96 out of 5 average rating, 49 reviewsCozy 2 Bedroom Valparaiso Cottage
Jul 16 – 23
Tiny home in Michigan City
4.97 out of 5 average rating, 76 reviewsThe Studio at the Dunes
Feb 24 – Mar 3
Home in Trail Creek
4.99 out of 5 average rating, 68 reviewsLeo Lodge
Feb 7 – 14
Home in Porter
5.0 out of 5 average rating, 31 reviewsDunes Woodland
Nov 29 – Dec 6
Home in Porter
4.93 out of 5 average rating, 43 reviewsBrand New Dunes Escape
Mar 28 – Apr 4
Condo in Portage
5.0 out of 5 average rating, 53 reviewsLuxury Waterfront 2 Bedroom Condo by Lake Michigan
Sep 15 – 22
Condo in Portage
4.94 out of 5 average rating, 67 reviewsUnsalted Stay - Waterfront Condo
Aug 17 – 24
Home in Chesterton
4.95 out of 5 average rating, 38 reviewsThe H'Art of Chesterton
Oct 23 – 30
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.
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