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Our top choices for Chesterton vacation homes
Vacation Home in Chesterton
Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes9.8 out of 10, Exceptional, (63)
"This place was great. It was very spacious, clean, and close to restaurants and grocery stores. The host was very communicative and answered any questions we had very quickly. The house was easy to find and parking was right in front of the house. The neighborhood was quiet and safe."
Christine C.
$301 nightly
The price is $337
Jan 4 - Jan 5, 2026
Total with taxes and fees
Vacation Home in Chesterton
Balcony/Patio/ Separate Fenced Yard + Beach, Park & Downtown+close to Chicago9.0 out of 10, Wonderful, (9)
"Excellent spot for several people to stay and enjoy the Dunes. Clean, quiet, centrally located to lots of Dunes hotspots. Thanks for the great stay!"
Nick R.
$287 nightly
The price is $321
Dec 28 - Dec 29
Total with taxes and fees
Vacation Home in Chesterton
Balcony/Patio/ Fenced Yard/ Attached Garage/near Beach, Park /close to Chicago9.4 out of 10, Exceptional, (3)
"I enjoyed my short stay and visit to The Indiana National Dunes. The Host was friendly and she put special effort into setting the place up for my stay. I 100% would rent again from this host and would recommend "
T J.
$348 nightly
The price is $390
Dec 24 - Dec 25
Total with taxes and fees
Vacation Home in Chesterton
NEW! Beautiful Riverfront Home on 10 Acres!8.0 out of 10, Very Good, (9)
"Very tranquil and private stay. The house was clean and comfortable, the fire pit was very nice,. CLose to town, and close to the beach. We loved it."
Jeff S.
$349 nightly
The price is $391
Dec 28 - Dec 29
Total with taxes and fees
Vacation Home in Chesterton
Cozy Retreat w/Hot tub Indiana dunes Beaches Trails10.0 out of 10, Exceptional, (12)
"This rental was amazing!!! So very clean, amazingly comfortable bed, and every amenity thought off. You will not be sorry that you stayed here. We hope to stay again. "
Leiann N.
$286 nightly
The price is $320
Dec 29 - Dec 30
Total with taxes and fees
Vacation Home in Chesterton
Modern Comfort 3-bedroom house in lovely Chesterton with cool breeze and charm$404 nightly
The price is $452
Dec 29 - Dec 30
Total with taxes and fees
Vacation Home in Michigan City
Grand Reunion House 2 / Hot Tub / Pet Friendly / Duplex10.0 out of 10, Exceptional, (5)
"Great option for a quick weekend trip to the Dunes. Clean, comfy and good communication from the host."
Dillon K.
$257 nightly
The price is $273
Dec 28 - Dec 29
Total with taxes and fees
Vacation Home in Downtown New Buffalo
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach10.0 out of 10, Exceptional, (29)
"It was a lovely stay! Very clean and it was awesome I could take my dog with me :)"
Roxie
$296 nightly
The price is $302
Jan 5 - Jan 6, 2026
Total with taxes and fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesterton Hotel Reviews
Four Winds Casino Resort – New Buffalo
10/10 Excellent
Find out more about Chesterton
Chesterton Vacation Homes information
Number of reviews | 340 |
|---|---|
Accommodation | 723 Vacation Homes |
Lowest Price | $162 |
Highest Price | $533 |
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