House vacation rentals in Chesterton

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Popular amenities for Chesterton house rentals

House rentals with a pool

Superhost
Home in Michigan City
4.85 out of 5 average rating, 54 reviews

Vip! 4BD 5 min to Lake, W pool heater.

BrandonRating, 5 stars4 days ago
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.
Guest favorite
Home in Buchanan
4.92 out of 5 average rating, 201 reviews

Beautiful RETREAT in the country

LisaRating, 5 stars3 weeks ago
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.
Guest favorite
Home in Berrien Springs
4.9 out of 5 average rating, 125 reviews

Lake House Retreat with a Pool

KatelynRating, 5 stars1 week ago
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.
Superhost
Home in Michigan City
4.92 out of 5 average rating, 107 reviews

Beautiful home with Beach views in Beachwalk

SamanthaRating, 5 stars8 months ago
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!
Guest favorite
Home in Michigan City
4.96 out of 5 average rating, 176 reviews

5 Bedroom Luxury Home In Heart of Beachwalk Resort

JeffRating, 5 stars1 month ago
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
Top guest favorite
Home in Chesterton
4.98 out of 5 average rating, 42 reviews

Pool House near the Indiana Dunes

AlaynaRating, 5 stars2 weeks ago
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.
Top guest favorite
Home in Union Pier
4.95 out of 5 average rating, 155 reviews

New Hot Tub Community pool Union Pier

JanelleRating, 5 stars6 days ago
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.
Guest favorite
Home in Union Pier
4.85 out of 5 average rating, 180 reviews

New Buffalo / Union Pier Pool Hot tub 6 Bedroom

KimberlyRating, 5 stars2 weeks ago
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

Top guest favorite
Home in Valparaiso
5 out of 5 average rating, 8 reviews

Long Lake Retreat

SaadRating, 5 stars1 week ago
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.
Guest favorite
Home in Porter
4.98 out of 5 average rating, 40 reviews

National Park / Lake Michigan Neighbor

SantosRating, 5 stars4 weeks ago
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.
Superhost
Home in Chesterton
4.79 out of 5 average rating, 76 reviews

Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home

KieranRating, 5 stars1 month ago
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!
Superhost
Home in Valparaiso
5 out of 5 average rating, 9 reviews

Serene Retreat in Beauty Creek

ErinRating, 5 stars1 week ago
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!
Guest favorite
Home in Michigan City
4.95 out of 5 average rating, 37 reviews

Lake Trail Cottage(NO Cleaning Fee!)

KatherineRating, 5 stars5 days ago
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.
Superhost
Home in Portage
4.88 out of 5 average rating, 26 reviews

Welcome Home

KathyRating, 5 stars4 months ago
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!
Top guest favorite
Home in Porter
5 out of 5 average rating, 14 reviews

Indiana Dunes Modern Farmhouse

KristiRating, 5 stars5 days ago
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!
Guest favorite
Home in Chesterton
5 out of 5 average rating, 17 reviews

INDIANA DUNES/LAKE MICHIGAN/CHESTERTON HOUSE

RebeccaRating, 5 stars9 months ago
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

Guest favorite
Home in Porter
4.88 out of 5 average rating, 41 reviews

The Waverly Retreat

JohannaRating, 5 stars2 weeks ago
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!
Guest favorite
Home in Michigan City
5 out of 5 average rating, 8 reviews

Charming Retreat Close to the Beach

AnnRating, 5 stars3 weeks ago
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!
Superhost
Home in Portage
4.82 out of 5 average rating, 56 reviews

Hamstrom Hideaway

GeorgiaRating, 5 stars1 week ago
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!
Superhost
Home in Michigan City
5 out of 5 average rating, 5 reviews

Top Summer Dates Still Available 1 Mile To Beach

RichardRating, 5 stars1 week ago
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!
Guest favorite
Home in Porter
4.89 out of 5 average rating, 89 reviews

New Dunes Escape

EmilyRating, 5 stars1 week ago
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!
Top guest favorite
Home in Michigan City
4.97 out of 5 average rating, 38 reviews

Birch Nest Cottage by The Lake

MelissaRating, 5 stars6 days ago
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!!
Top guest favorite
Home in Michigan City
5 out of 5 average rating, 38 reviews

New! Charming Retreat in the Heart of MC-King Bed

OliviaRating, 5 stars1 week ago
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!
Superhost
Home in Michigan City
4.87 out of 5 average rating, 67 reviews

Roomy & Cozy 3 Bd 2Ba just mins from Indiana Dunes

CaraRating, 5 stars1 month ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. Indiana
  4. Porter County
  5. Chesterton
  6. House rentals