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
Cabin in Michigan City
4.95 out of 5 average rating, 399 reviewsLittle Copper Cabin
Mar 10 – 17
Home in Portage
4.92 out of 5 average rating, 148 reviewsNewly Renovated with Finished Basement
Jan 27 – Feb 3
Home in De Motte
4.96 out of 5 average rating, 207 reviewsCountry Cottage
Nov 25 – Dec 2
Cottage in Merrillville
4.89 out of 5 average rating, 184 reviewsThe Hideaway
Jun 17 – 24
Home in Valparaiso
5.0 out of 5 average rating, 112 reviewsLonely Pine Guest House: A Peaceful, Wooded Stay
Dec 26 – Jan 2
Home in Michigan City
4.98 out of 5 average rating, 229 reviewsHouse of Zen: Peaceful Modern Cabin on Tryon Farm
Sep 3 – 10
Apartment in Michigan City
4.95 out of 5 average rating, 104 reviewsMichigan City full apartment near National Park #4
Jan 13 – 20
Apartment in Valparaiso
4.85 out of 5 average rating, 112 reviewsCharming: Cute 2-bedrooms Valpo University
Aug 21 – 28
Other great vacation rentals in Chesterton
Condo in Portage
4.96 out of 5 average rating, 78 reviewsCozy 1 bedroom condo on Marina near Lake Michigan
Mar 7 – 14
Home in Trail Creek
4.99 out of 5 average rating, 68 reviewsLeo Lodge
Apr 3 – 10
Cottage in Valparaiso
4.96 out of 5 average rating, 49 reviewsCozy 2 Bedroom Valparaiso Cottage
Jun 17 – 24
Home in Porter
5.0 out of 5 average rating, 31 reviewsDunes Woodland
Feb 23 – Mar 2
Home in Porter
4.93 out of 5 average rating, 43 reviewsBrand New Dunes Escape
Mar 26 – Apr 2
Guest suite in Gary
4.98 out of 5 average rating, 48 reviewsBeachfront- Lake Michigan- 2bd/2bath -Heated Pool
Feb 9 – 16
Condo in Portage
4.94 out of 5 average rating, 67 reviewsUnsalted Stay - Waterfront Condo
Sep 3 – 10
Home in Chesterton
4.95 out of 5 average rating, 38 reviewsThe H'Art of Chesterton
Oct 21 – 28
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
G$2,084 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.
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