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Search results; Over 1,000 homes in Chesterton

Loft in Chesterton
Treehouse loft with pool, hot tub, sauna
1 bedroom, 2 beds, 1 private bath
Aug 16 – 21
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4.95 out of 5 average rating, 19 reviews
Top guest favorite
Home in Chesterton
Vintage home 10 minutes from the Dunes
4.96 out of 5 average rating, 67 reviews, 2 bedrooms, 3 beds, 1 bath
Sep 8 – 13
Guest favorite
Home in Chesterton
Craftsman home minutes from Lake Michigan
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 4 beds, 2 baths
Sep 13 – 18
Apartment in Chesterton
Modern retreat minutes from the Dunes
4.79 out of 5 average rating, 14 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 30 – Sep 4
Top guest favorite
Home in Chesterton
Fire pit and patio near the Dunes
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 3 beds, 2.5 baths
Aug 26 – 31
Superhost
Townhouse in Chesterton
Pool, fire pit, and beach access nearby
4.81 out of 5 average rating, 63 reviews, 3 bedrooms, 5 beds, 2 baths
Aug 23 – 28
Superhost
Home in Chesterton
Fenced yard with a fire pit
4.8 out of 5 average rating, 122 reviews, 3 bedrooms, 8 beds, 2 baths
Sep 7 – 12
Top guest favorite
Guesthouse in Chesterton
Vaulted skylights and a fire pit
4.92 out of 5 average rating, 417 reviews, 1 bedroom, 2 beds, 1 bath
Sep 8 – 13
Top guest favorite
Home in Chesterton
Retro 1950s Estate w Hot Tub Near Indiana Dunes
4.98 out of 5 average rating, 96 reviews, 4 bedrooms, 7 beds, 2.5 baths
Aug 14 – 19
Top guest favorite
Home in Chesterton
Remodeled 1800s home near the Dunes
4.97 out of 5 average rating, 182 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 16 – 21
Top guest favorite
Apartment in Chesterton
Historic home, walk to downtown Chesterton
4.96 out of 5 average rating, 78 reviews, 3 bedrooms, 3 beds, 1 bath
Aug 30 – Sep 4
Top guest favorite
Bungalow in Chesterton
Barn-turned-guesthouse on 4 wooded acres
4.98 out of 5 average rating, 119 reviews, 2 bedrooms, 2 beds, 1 bath
Sep 13 – 18
Guest favorite
Home in Chesterton
5-acre retreat near Indiana Dunes
4.83 out of 5 average rating, 420 reviews, 1 bedroom, 1 bed, 1 bath
Sep 11 – 16
Home in Chesterton
10 minutes from Indiana Dunes National Park
4.78 out of 5 average rating, 9 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 25 – 30
Top guest favorite
Guesthouse in Chesterton
Coastal cottage across from European Market
5.0 out of 5 average rating, 49 reviews, 1 bedroom, 4 beds, 1 bath
Aug 23 – 28
Guest favorite
Apartment in Chesterton
Historic home, walk to downtown Chesterton
4.94 out of 5 average rating, 66 reviews, 2 bedrooms, 4 beds, 1 bath
Aug 18 – 23
Top guest favorite
Guesthouse in Chesterton
Secluded on 2 wooded acres with pool
4.97 out of 5 average rating, 99 reviews, 1 bedroom, 1 bed, 1 bath
Sep 13 – 18
Top guest favorite
Guest suite in Valparaiso
Geodesic dome and hot tub on Long Lake
4.98 out of 5 average rating, 170 reviews, 1 bedroom, 2 beds, 1 bath
Sep 20 – 25
Guest favorite
Home in Chesterton
Fireplace, fire pit, and a game room
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 7 beds, 2 baths
Aug 16 – 21