
Cabin holiday rentals in Chesterton
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Top-rated cabin rentals in Chesterton
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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!

“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.

NEW- Cozy Michiana cabin walking distance to lake
We had a great stay at Julia's place. It was exactly what was described and shown in the pictures. Beautiful and very quiet neighborhood. The home was older but you could only tell because of the original floors which had the charming creaks of original wood floors. Everything else has been upgraded and in great shape. Would be a great place anytime of year. Pool was closed obviously but the hot tub was perfect and the steam shower was nice. Only suggestion is that if you are arriving late definitely take a flashlight...it is very dark after the sun goes down. It was exactly what we needed. Julia was great with communication and available for anything we needed! Already have had discussions about coming back in the summer!

Cabin on 7 acres minutes to Lake Max & Bass Lake!
Secluded and quiet cabin. Lots of space around the kitchen, amazing deck, and tons of sleeping options.
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 !

Log Cabin - Private - Pets Welcome
Cute log cabin, a bit rustic, but it added to the charm. Portia was very responsive to questions & helpful.

Firefly near Warren Dunes Red Arrow Cabins
Kristal and John were great hosts. gave is clear and fast answers when we needed. Their property is very cozy, clean and comfortable...Wish we had more time to enjoy the staying longer. The only 2 negative points were: The weak WiFi signal in our cabin, not good enough to download and watch a movie during the night. No locker on the restroom door, so the sliding door kept on opening all the time, while one was using the restroom.

Rustic Lodge -Oak Tree Lodge
5 Stars !! We had a great stay at Linda’ s place! The home was exactly as described—clean, comfortable, and well-located. Check-in was smooth, and the host was very responsive and helpful throughout. Would definitely stay here again.

Black Cabin Getaway in Beautiful Woods I Valpo
We were very thankful for a quiet and clean place to lay our heads during our trip. It met our needs.

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 pine cabin at the lake.
We loved our time at the cottage! Lynette was the most gracious host and we were fully stocked the whole weekend! The location is beautiful and our stay was spectacular, we will be back!
Private cabin rentals

Sister Lake Cottages - Unit 3
cozy comfortable cabin in a fabulous setting between lakes and beautiful country setting can walk to bar and restaurants on water great stay!!! 👍 Good value. Recommend!

Rustic but chic cottage on hill at Dewey Lake
Lynette's cottage is incredible and full of history and nostalgia. Everything was absolutely perfect. From the comfortable beds, well stocked kitchen, to the awesome sun porch overlooking the vintage playground and the beautiful lake. Fun and relaxation was had by all the ages of our group and we a can't wait to come for longer next season.

Waterfront Cable Lake Cabin w/ Grill!
We had a nice time relaxing by the lake would definitely stay here again. Very convenient walking outside and lake is right outside the door our family and little baby enjoyed it up here

Sister Lake Cottages - Unit 4
Great place and a great location would stay here again

Sister Lake Cottages - Unit 2
We have stayed here multiple times and will continue to for as long as it's available!

Indiana Dunes Cabin WITH Bunk/Rec Room!
If I could give this place 6 stars I would! Jeannie was a great host and the cabin was well over our expectations! Check in was seamlessly and everything worked perfectly. The bunk beds were awesome and everything was clean, tidy and above our expectations. Jeannie also was very responsive during our stay and we had no issues. 100% would stay again.

Sister Lake Cottages - Unit 7
We enjoy staying there that was our 2nd time and will be booking again.

Sister Lake Cottages - Unit 1
The place is just fantastic if you’re looking for peace and quiet and you want to get away from the big city life wherever you live this is the place to come and enjoy the country fresh vegetables, fruit dairy freshwater minutes away from Lake Michigan +10 sister Lakes walking distance to two of them. I can’t say enough Highly recommended. And budget friendly prices and the staff and team are fantastic.
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- Indiana Dunes National Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Warren Dunes State Park
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- University of Notre Dame
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park Zoo
- Lincoln Park
- Wicker Park
- Museum of Science and Industry
- Chicago History Museum
- Willis Tower
- Potato Creek State Park
- Brookfield Zoo
- Flossmoor Golf Club
- Garfield Park Conservatory