
Cabin vacation rentals in Chesterton
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Top-rated cabin rentals in Chesterton
Guests agree: these cabins 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 cabin rentals
Cabin rentals with a hot tub

Walk 2 Lake/Shops | Hot Tub | King Bed | Fireplace
Clean, comfortable cabin with a nice fireplace.

Secluded Upscale Lodge. Hot Tub, Sauna & Golf Cart
Great stay in New Buffalo!

Unique 3-bedroom Aframe!
Sarah’s beautifully built A-frame home was the perfect base camp for our weekend away to celebrate my partner’s 40th birthday. The neighborhood was peaceful and quiet. We enjoyed the fire pit and the hot tub. Getting to downtown Three Oaks was a breeze and a public beach was a mile-ish down the road. We would love to come back for another visit!

Cozy Serene Cabin by Lake MI&Dunes Private Hot Tub
Our stay was nothing short of amazing! The airbnb was so clean and so nice! We enjoyed our stay and would love to make the trip back up and stay again!

Cozy Cabin by Lake MI & Dunes with private Hot Tub
The cozy cabin was the perfect getaway for my husband and I! It was the perfect amount of peacefulness we knew we needed. The place was adorable and the hot tub was really nice!

“Hickory Haven” - 6 Acre Cabin Near Notre Dame
Location was very private. House was full of games and toys, wonderful for families with multiple kiddos. Would highly recommend d

Vintage Cabin Wonderland: Welcome to Stonewood
Very relaxing cabin and quiet/quaint neighborhood. Even though you are in a neighborhood, you have privacy. We enjoyed the views and nature sounds. The private beaches are beautiful. Great place to relax. Cabin was cozy. The bed and bedding were sooooo comfy.

Cozy Cabin at Coppertop Barn
Such a great place for a weekend getaway! Very cozy and has everything you need for the weekend. The hot tub was SO much fun & an amazing way to wind down for the night. Would definitely recommend for anyone looking to get away for a few!
Pet-friendly cabin rentals

Idyllic A-frame in Michigan’s Harbor Wine Country
Thank you for letting us stay at your lovely home on Easter weekend! We loved the place and felt like home. Lots of light and the home structure and decor is very special and cozy. Callie was very welcoming and responsive. We were very close to wineries at Baroda county and St. Joseph. We look forward to come back soon!

Floyd's Cabin Lakeside Mich
Had a wonderful restorative weekend here. Would come back !

Rustic Lodge -Oak Tree Lodge
We had a nice getaways weekend at Linda’s! It was so nice to let our puppy freely run as we came from the city. The barn was decorated for Valentine’s Day and Linda left us a delicious treat. The couches were extremely comfortable and we slept well in a dark room. We’d love to return!

Woodland Cabin Escape, walk to Lake Michigan
The cabin was perfect for a couple looking to escape to Lake Michigan. Set back in the trees a bit, it really does feel secluded. The large windows throughout the home mean we almost never had to use lights until it was really dark out. Easy walking access to the beach. Short drives can take you up to New Buffalo or down to Michigan City. Only thing to be careful about driving is to look out for wild life. Deer like to eat right next to the roads and can startle as your car approaches. 10/10 would recommend staying here. Jen’s guide book and recommendations were 100% spot on.

Knotty but Nice-sleeps 6-one minute to lake
This whole place was so nice. We had a blast giving candy out to the kids during the Halloween festivities. Thanks to our host for letting us know it was going on.

Serene Log Cabin Forest Retreat
Jesse's cabin was very quiet and peaceful. Everything is exactly like the pictures, the kitchen is well stocked, also the bathrooms. The beds are very comfortable, the windows have blackout curtains which allowed us to sleep in late every day... The working station and WiFi were also great. Beautiful surroundings and a short drive to local stores and services. A full disclosure: there's a train line somewhere nearby in the area but we practically couldn't hear it from inside the cabin. Never bothered us and it didn't wake anybody up. We just noticed it when walking outside and one train happened to pass by during the day. Overall a great experience, the cabin is very relaxing and perfect for a relaxing getaway, and Jesse is very responsive and attentive. We are planning to come back when time permits.

Cozy Cabin on the grounds of a riding stables
What a hidden gem! We loved our stay at Claudia’s place. It’s quiet and out of the way yet so close to everything. The property is a unique experience. The barn staff was so so nice including the barn cat who we fell in love with. The cabin is pretty spacious and clean for being an older cabin. It feels like an old cabin but also has a few nice updates like the kitchen and bathroom. There was plenty of cleaner, towels, paper towels, toilet paper and anything else we needed. Would definitely come back any time!
Private cabin rentals

Beautiful Rustic Cabin for Two!
great little place, private and comfortable

Steps to the beach at luxury cabin 1hr to Chicago
This is a beautiful house and Amanda has everything ready before our arrival. The house is clean and I just love the ecstatic. We have a lovely girl's night and would love to come back maybe a warmer summer time to check out the beach and outside. We were a little bit confused about the light switches though even Amanda already labeled everything.

Cozy Cabin Minutes from Michigan's Harbor Country
Patti was a great host. Super polite and responsive. Would stay here again when it gets warmer outside.

Pet Friendly Cabin in the Woods - Spring Getaway
A+ absolutely loved this unique cabin! It’s even better in person than in the listing with very cool decor and design. It’s secluded yet close to everything - best of both worlds!

3 acres of Privacy, Pup heaven! 7 minutes 3Oaks!
wow! this place is dog and people paradise. the yard is beautiful and spacious for our dogs to run - they stay close and it look amazing with the snow. love her style and felt very cozy and at home! Had what we needed and gave helpful suggestions and tips. thank you and would love to stay again!

The Little House at Tryon Farm
The place was clean, compact and modern. We loved our hikes in the surrounding woods. Jason was super responsive. Highly recommend!

Cozy Cabin by Lake MI & Dunes with private Hot Tub
The cozy cabin was the perfect getaway for my husband and I! It was the perfect amount of peacefulness we knew we needed. The place was adorable and the hot tub was really nice!

Cozy Cabin at Coppertop Barn
Such a great place for a weekend getaway! Very cozy and has everything you need for the weekend. The hot tub was SO much fun & an amazing way to wind down for the night. Would definitely recommend for anyone looking to get away for a few!
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Warren Dunes State Park
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Humboldt Park
- University of Notre Dame
- Museum of Science and Industry
- Lincoln Park Zoo
- Chicago History Museum
- The Field Museum
- 875 North Michigan Avenue
- Wicker Park
- Potato Creek State Park
- Willis Tower
- Lincoln Park
- Garfield Park Conservatory
- Chicago Cultural Center
- Promontory Point
- Silver Beach Carousel
- Odyssey Fun World