
Holiday rentals in Chesterton
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Top-rated holiday rentals in Chesterton
Guests agree: these stays are highly rated for location, cleanliness and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesterton holiday rentals
Other great holiday rentals in Chesterton
Top guest favourite

Home in Porter
5 out of 5 average rating, 20 reviewsIndiana Dunes Getaway! A 5 Bed, 5 Bath Farmhouse

Campervan/Motorhome in Chesterton
4.5 out of 5 average rating, 4 reviewsCreekside

Home in Porter
4.83 out of 5 average rating, 216 reviewsModern Indiana Beach Home Near Lake Michigan
Top guest favourite

Private room in Valparaiso
4.99 out of 5 average rating, 165 reviewsLovely bedroom, bath, parking, 5 blks to downtown.

Home in Valparaiso
5 out of 5 average rating, 3 reviewsThe House Near The Lakes
Top guest favourite

Private room in Valparaiso
4.93 out of 5 average rating, 324 reviews15 min. to beach. Modern country home.5 min. to VU
Top guest favourite

Home in Valparaiso
5 out of 5 average rating, 5 reviewsThe Jefferson House
Top guest favourite

Private room in Westville
4.94 out of 5 average rating, 424 reviewsNice private room in country house
Quick stats about holiday rentals in Chesterton
Total rentals
50 properties
Nightly prices starting at
₹862 before taxes and fees
Total number of reviews
4.4K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
Destinations to explore
- Downtown Chicago Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- South Haven Holiday rentals
- Saugatuck Holiday rentals
- Holland Holiday rentals
- South Side Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Chicago Holiday rentals
- Rentals with a firepit Chesterton
- Cabin rentals Chesterton
- Family-friendly rentals Chesterton
- Rentals with a washing machine and dryer Chesterton
- Family-friendly rentals Chesterton
- Pet-friendly rentals Chesterton
- Rentals with a patio Chesterton
- House rentals Chesterton
- Rentals with outdoor seating Chesterton
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Warren Dunes State Park
- Oak Street Beach
- Humboldt Park
- Shedd Aquarium
- Frank Lloyd Wright Home and Studio
- Guaranteed Rate Field
- 875 North Michigan Avenue
- University of Notre Dame
- The Field Museum
- Lincoln Park
- Washington Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Garfield Park Conservatory
- Wicker Park
- Willis Tower
- Lincoln Park Zoo
- Potato Creek State Park
- Silver Beach Carousel
- The 606