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Browse Select Chesterton Vacation Homes

Adorable cottage in the Michiana Shores area! Close to Lake Michigan and Dunes

10.0 out of 10, Exceptional, (75)
"Beautiful home...It was close to all the places we wanted to see."
Adorable cottage in the Michiana Shores area! Close to Lake Michigan and Dunes

Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

10.0 out of 10, Exceptional, (197)
"We loved our stay here. I can’t wait to come back in the summer months"
Family Retreat-Beachwalk-Grill-AC-Free WiFi-Pool Table-Bikes-Grill-Golf Cart

Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.

9.6 out of 10, Exceptional, (227)
"We enjoyed our stay. Everything was picturesque and would definitely recommend staying here."
Beautiful Family Cottage in Beachwalk-Grill-AC-Free Wifi-Kids Haven.

Kid-friendly Michiana cottage! Summer dates open - including 4th of July!

10.0 out of 10, Exceptional, (58)
"Loved this place and so clean and perfect for our girls weekend!"
Kid-friendly Michiana cottage! Summer dates open - including 4th of July!

Wonderful Downtown Gem W/ Fast WiFi, Firepit, & Central AC - Walk to the Beach

9.0 out of 10, Wonderful, (23)
"Great location, everything is walkable. Master bedroom is fantastic."
Wonderful Downtown Gem W/ Fast WiFi, Firepit, & Central AC - Walk to the Beach

Walk to the beach! Great modern home with spring and early summer availability!

9.8 out of 10, Exceptional, (118)
"Great location. Close to the beach, fun restaurants, and stores. Perfect for families. Spacious common areas and lots of bathrooms. "
Walk to the beach! Great modern home with spring and early summer availability!

Cozy house with hot tub, firepit, near restaurants + near beach

2.0 star property
9.8 out of 10, Exceptional, (11)
"Host was very nice and extremely quick to respond to texts or calls. House was clean and in great condition. 10/10"
Cozy house with hot tub, firepit, near restaurants + near beach

Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants

10.0 out of 10, Exceptional, (74)
"This house is a great setup and well taken care of. The owners are very responsive and location is close to everything."
Red Oak-5 bedroom with in ground pool, fireplace-walk to restaurants

Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!

10.0 out of 10, Exceptional, (168)
"This property is beautiful with a lot of space, bedrooms, and bathrooms. The location was perfect for walking to the beach, restaurants, and shopping. Can't wait to visit again!"
Warm late summer dates still open in Sept 2025: 1-4, 7-11, 15-19, 21-26. Enjoy!

Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!

9.2 out of 10, Wonderful, (65)
"Had the best weekend at this house. The house was clean, updated, and had everything we could need. Will be staying again. "
Hot tub open all year! Private heated pool, sleeps 10 near downtown New Buffalo!

Charming & cozy in-town retreat in the heart of New Buffalo

10.0 out of 10, Exceptional, (159)
"We loved staying here! It was perfect for our young family and dogs. We really enjoyed the backyard, fireplace, and walkability. Hope to return!"
Charming & cozy in-town retreat in the heart of New Buffalo

Adorable Downtown Cottage with Firepit, Fireplace, & Yard - Walk Everywhere

9.6 out of 10, Exceptional, (44)
"Cottage was adorable and very clean. We enjoyed the fireplace and the view of the backyard. Cottage was comfortable and charming. "
Adorable Downtown Cottage with Firepit, Fireplace, & Yard - Walk Everywhere

House of TarTar with year long hot tub next to adorable downtown Valparaiso

10.0 out of 10, Exceptional, (74)
"Great place to stay, easy check in and check out. Very nice place we will be back to visit."
House of TarTar with year long hot tub next to adorable downtown Valparaiso

Charming 3-bedroom house in Michigan City is handicapp friendly with a ramp.

9.4 out of 10, Exceptional, (6)
"We stayed here for the accessibility, as one family member is in a wheelchair. The ramp was very useful and the layout made for easy moving about, but the throw rugs were a bit of an issue. The shower in the master suite is a poor design as the built in bench sets back too far from the shower heads and without a door, the water goes out onto the floor. Luckily, we brought a shower stool with us. The house was very nicely decorated and overall, a comfortable place to stay. Cookware could be...
Charming 3-bedroom house in Michigan City is handicapp friendly with a ramp.

Amazing Lake Views, Beach Access, Hot Tub, Fire Pit, Screened Porch & Game Room

10.0 out of 10, Exceptional, (209)
"We had a great stay; the layout was great for our family vacation."
Amazing Lake Views, Beach Access, Hot Tub, Fire Pit, Screened Porch & Game Room

Charming 1-bedroom apt in house by creek with AC, in delightful Portage

10.0 out of 10, Exceptional, (4)
"Easy check in and wonderful host. Great place to stay near Indiana Dunes and train station to Chicago. "
Charming 1-bedroom apt in house by creek with AC, in delightful Portage

Red Zen | HotTub-all yr | Firepit | Grill | DogsOK

9.6 out of 10, Exceptional, (31)
" Loved it! Very cozy, and warming home, good communication and very attentive. :) "
The price is CA $253
CA $483 total
includes taxes & fees
Aug 18 - Aug 19
Red Zen | HotTub-all yr | Firepit | Grill | DogsOK

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

8.4 out of 10, Very good, (37)
"The yard is awesome, of course the hot tub at the top of the hill was the best, and we enjoyed the firepit as well. The house was a tidy little cottage at which we enjoyed our stay. It’s within a short walk to the National Park and downtown Miller Beach. The neighborhood is fine, pretty secluded, and still close to most attractions."
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

The White House - spacious 5 bedroom, with hot tub - blocks from everything!!!!

10.0 out of 10, Exceptional, (91)
"Our family had a great time at this location."
The White House - spacious 5 bedroom, with hot tub - blocks from everything!!!!

Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach

10.0 out of 10, Exceptional, (19)
"Quiet area and warmly decorated. "
The price is CA $455
CA $882 total
includes taxes & fees
Sep 7 - Sep 8
Eagles Beach Nest 2:Pet-Friendly*Fenced*Walk2Beach
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