
House vacation rentals in Chesterton
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Top-rated house rentals in Chesterton
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Chesterton house rentals
House rentals with a pool

Vip! 4BD 5 min to Lake, W pool heater.
Host was very responsive and helpful. we enjoyed our stay and would definitely return. Kids loved the pool and outside area! Great location and the house is decorated very beautifully! The kitchen provides everything you need to cook a meal also.

Beautiful RETREAT in the country
It was a pleasure meeting Antoinette and her family. They are extremely welcoming. The property is amazing especially if you like horses, donkeys, chickens and outdoor cats. We definitely recommend a stay there.

Lake House Retreat with a Pool
This house was so beautiful and was a perfect place to spend a girl’s weekend! Would recommend over and over again and would definitely stay here again! Mike was also very quick at responding (even on the weekend) and when something wasn’t right he was very quick it fix it.

Beautiful home with Beach views in Beachwalk
Well-maintained house, spotless upon arrival, great view of the area from the kitchen. Ice machine was a great touch especially with a bunch of people in the house! Would definitely come back!

5 Bedroom Luxury Home In Heart of Beachwalk Resort
We all walked in and said WOW! It was beautiful and had so much charm. We have stayed in many rentals and this was by far the cleanest and most organized. We traveled with 3 couples and there was plenty of room to gather and socialize and room to just chill by yourself. The boardwalk made for a wonderful morning walk. Brittany was a terrific host answering any questions I had and providing a list of thing to do in the area. Certainly worth the money! We would definitely stay again. Rita

Pool House near the Indiana Dunes
The location was so peaceful and close to everything (10 mins from the dunes). The house was comfy and had everything you could possibly need. Melissa thought of everything! The pool.. OMG the best! The heater made the water PERFECT! Made it even more special that we could bring our dogs. The fully fenced yard was perfect. Will definitely be coming back.

New Hot Tub Community pool Union Pier
I recently stayed with a few of my girlfriends for the weekend here. My friends and I absolutely loved this place. It was in a picturesque setting, and we loved how cozy it was. We especially enjoyed having the hot tub, the access to the public pool with clubhouse, and being able to walk to the beach to see the sunsets. We were able to enjoy a fire every night within the fire pit and loved being near the woods and the pond. Kristen was extremely responsive and a great host. My girlfriends and I would definitely stay again. We absolutely loved it here! Location is perfect for visiting lots of restaurants, wineries, and enjoying the best of Southwest Michigan.

New Buffalo / Union Pier Pool Hot tub 6 Bedroom
We had an amazing stay to celebrate a milestone birthday with my extended family! The house comfortably fit 4 families and a labradoodle and was excellent for the 5 kiddos. The heated pool and hot tub were fantastic for cooler than expected temperatures Memorial Day weekend and kept the kids entertained. We opted to cook and grill at the house and had everything we needed. The house is also super close to the beautiful New Buffalo beach. We will be back!
Weekly house rentals

Long Lake Retreat
Quaint, peaceful, perfect for a couple, overlooking a gorgeous lake. 10 mins drive to downtown. Great WiFi and thankfully no TV. Loved every minute. All amenities included. Would like to stay again.

National Park / Lake Michigan Neighbor
Perfect for our trip. We attended the Indiana Dunes Bird Festival. This place was perfectly located for all of our activities. Later this summer if we go up for a beach getaway we would stay again. Walkable to deep dish pizza too. Great host. Very responsive. Thanks for the great stay.

Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home
Great house for the value! Clean and lots of amenities! Wish we visited in summer as fenced backyard is great! Stairs to second floor are steep but in good condition with handrail! There are local trains that are present throughout the day/night, but their sound didn’t bother us 😊 Overall a great value and lovely vintage home! Host was very responsive and friendly! Thank you!

Serene Retreat in Beauty Creek
Such a beautiful townhome. It was a perfect place to get ready for my wedding. Beautiful decor and lots of natural light. It was a lovely space. Highly recommend!

Lake Trail Cottage(NO Cleaning Fee!)
A great stay close to the Dunes! We took the South Shore Line into Chicago and did the 3 Dune Challenge and both were great. Highly recommend this place.

Welcome Home
Great place to stay while we were visiting our grandchildren for the weekend! It was nice to have the kitchen to make coffee and breakfast in the morning. Comfortable bed and private, quiet location. Thanks again!

Indiana Dunes Modern Farmhouse
Perfect location to The Dunes! The place was comfortable, clean and cozy for a family birthday trip for 12 people. Plenty of space for all ages. The property was private, large and beautiful. If we’re ever in the area again, this is where we’ll stay for sure. What a great trip!

INDIANA DUNES/LAKE MICHIGAN/CHESTERTON HOUSE
We had such a great stay earlier this month, so we decided to come back for the long weekend ! Thanks again Lori for a wonderful stay in your lovely home and being a great host - we look forward to coming back again !
Private house rentals

The Waverly Retreat
My family stayed at the Waverly Retreat for my son's wedding weekend. The location was perfect as the reception was at the Dunes Pavilion. We appreciated the space, cleanliness, attention to details, fully stocked kitchen and Kayla's assistance with everything. The master suite was gorgeous and the bathroom space allowed several of us to get ready at one time for the wedding. Thank you Kayla for a wonderful place to stay!

Charming Retreat Close to the Beach
Great size house, area close to everything and amazing communication! Had a partial power outage when staying and owners answered promptly and were attentive and super helpful. Would definitely stay again!

Hamstrom Hideaway
Tiffany and John were great host! The house perfectly matched the description and was the perfect spot for a short weekend trip. The house was very homey and had everything you could need. The big yard was a huge plus as we had our dog with us! Tiffany and John were very responsive and very accommodating throughout our stay especially when we had to add another person to our reservation half way through our stay. I would definitely recommend staying here as it definitely feels like a second home!

Top Summer Dates Still Available 1 Mile To Beach
Had the absolute pleasure of taking my wife to Rudy + Deanna's Airbnb to celebrate our first anniversary. Both co-hosts were very responsive, very friendly, and shared a ton of useful local knowledge for us to make our weekend special! The Airbnb itself was gorgeous - pristine inside with all the amenities you could need. The four of us (two dogs, yes they are pet friendly) had a wonderful time and would absolutely recommend this place to others wishing to visit Michigan City! Thanks again!

New Dunes Escape
Probably the best place we've stayed. Clean, organized, and exactly as described. The attention to small details makes you feel at home. Will book again if we go back!

Birch Nest Cottage by The Lake
We loved staying at Katrina’s place! It was very comfortable, clean and uncluttered. We felt right at home the minute we walked through the door. New Buffalo was a short drive away so had a nice dinner at the Stray Dog. We loved spending time down at the beach and then coming home to grill some steaks. Katrina was very helpful and super communicative during our stay! Thank you for a wonderful weekend away!!

New! Charming Retreat in the Heart of MC-King Bed
Eileen was a great host! The space was beautiful and plenty for my husband and our two kids. She was extremely responsive and went above and beyond to make sure our stay was great. Highly recommend if you’re looking to stay in Michigan City!

Roomy & Cozy 3 Bd 2Ba just mins from Indiana Dunes
This home is a lot bigger than it looks. The beds are comfy, the deck is very nice, fire pit was handy and the separate finished basement was a plus. Thank you for hosting us! I will come back if needed!
Quick stats about house rentals in Chesterton
Total rentals
40 properties
Nightly prices starting at
G$14,629 GYD before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Warren Dunes State Park
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- University of Notre Dame
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Lincoln Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Wicker Park
- Willis Tower
- Potato Creek State Park
- Washington Park Zoo
- Brookfield Zoo
- The 606
- Chicago Cultural Center