
House holiday 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.
Holiday rentals for every style
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Popular amenities for house rentals in Chesterton
House rentals with a pool

The Poolside Escape | Hot Tub | Arcade | Ping Pong
Had a great stay. Was great with communicating when needed.

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
We had a great stay!! The house was perfect for the five of us and our dog, with enough space for all of us to feel comfortable. The bathrooms were clean and the kitchen was well stocked. The pool was the best part! Melissa was super prompt when it seemed like the heat to the pool wasn’t running and we were back in there in no time - the heated water was perfect for this fall weather! We also tried some of the recommended spots and overall, this was exactly the quick getaway we needed!

New Hot Tub Community pool Union Pier
beautiful home and I love the energy and the location. will definitely stay again. I appreciate your time as well when I needed to reach out to you.

Home near the lake with an inground pool
Clean house and will definitely book again for our needs. Very comfortable with everything.

Luxury Living in Harbor Country|Hot Tub| Sleeps 10
The place was absolutely beautiful—clean, cozy, and well-designed. The location was perfect for a peaceful getaway, with the lake just a short walk away. Would definitely love to visit again!

Pool | Hot Tub | Backyard Oasis | Game Room | Fun
We had an amazing stay here. House was very clean, beds very comfortable and inviting. The kids loved the game room, especially the game tables. The hot tub was fun and relaxing and the pool looks great for when it will be heated. Large backyard - would just be careful with little kids as no gate right around pool, just around the whole backyard. We really enjoyed our stay and Todd was very responsive to all our questions and requests.
Weekly house rentals

18 acres | Arcades | Heated Pool | Hot Tub | Pond
We had an amazing and pleasant stay here, the place is beautiful, serene and breath taking. Brandon was super helpful and communicative. The house is well maintained and has all the amenities described. If you love nature, this is the place to be. The view to the pond is magnificent and I really enjoyed watching the sunset while enjoying a good conversation around the fire pit. Overall it was wonderful, affordable and will definitely recommend it to our family and friends!! Just a couple things to know: 1. The playground is across the path from the house and kind of out of sight, so if you were expecting to be in the hot-tub or pool while directly keeping an eye on the little ones, thats going to be impossible. 2. The Hot tub does not have a direct pond view because the pool is in front of it.

Indiana Dunes Park Getaway w/Firepit, Near Beach
Kelly’s place was wonderful. There’s a lot to enjoy here from a wonderful backyard with a fire pit, a lovely front porch, a chill side porch with a grill, a second floor balcony, and a sun room. The place was perfectly clean when I got there and they so nicely left out plenty of clean towels and sweatshirts for myself and my friends. I would definitely stay again if I came back to the area!

It's A Dog's Life
This place was perfect for a friends getaway from Chicago!! We loved the fire pits and cozy vibe throughout the property. So lovely all the dog’s life decor❤️ We really enjoyed being so close to Three Oaks, Union Pier, and Warren Dunes! Thank you Pam, you were a great host!!

Picture Perfect Lake House Steps from the Beach
Absolutely perfect in every way. I have booked a (lakefront)fall retreat for a group of 12 ladies six years in a row. This home is by far the best equipped! From cozy blankets on hooks near the outdoor seating areas, cushions stored clean and dry inside so the outdoor seating could be used easily, and very high-quality large amount of beach chairs available, I have never seen such great amenities at a beach home! Mattresses are very high-quality and bedding was soft and luxurious! We loved every second of our weekend!

In-town Lovely Home! Steps to Starbucks & Beach!
This was such a nice place for a quick family getaway. James was a great host. He was very responsive and checked in after the first night to make sure we had what we needed. Highly recommend this place to stay!

Long-Term Spacious House for Rent
Ruthanne was beyond helpful and attentive.

3BR w/sauna, tanning bed, hot tub 3.9 miles fromND
We had a e couples weekend for my birthday and we had everything we needed as far as amenities for adults. I would recommend this place to anyone including people with kids.

Sleeps 15, 7 bedrooms, 4 baths, 2 kitchens
My stay at this Airbnb was fantastic! The space was spotless, stylish, and fully equipped, making it feel like home. The beds were incredibly comfortable, and the cozy décor added a welcoming touch. Located in a quiet neighborhood near local attractions, it offered the perfect balance of convenience and privacy. While it was too cold to use the outdoor space, the overall experience was still great. The host was responsive when needed, ensuring a smooth and stress-free stay. I highly recommend this Airbnb for a relaxing and comfortable getaway!
Private house rentals

Vip! 4BD 5 min to Lake, W pool heater.
Stayed there for almost a month never had a problem really clean and a quiet neighborhood I’ll definitely stay there again and the host responds very quickly 100% recommend this house !

Serenity House on the River
Our group had an absolutely amazing stay! Everyone raved about how beautiful the property was—from the peaceful setting to the gorgeous interior. The hot tub was a favorite spot for unwinding, and the well-stocked, spacious kitchen made it easy (and fun!) to cook all our meals in. We also loved having a grill to use! The hosts were super responsive and helpful with any questions we had. I would highly recommend this home to any large group looking for a relaxing, well-equipped getaway with all the comforts of home.

Renovated french country lake home. 6bedroom/4bath
This house was perfect for our family. It was extremely well appointed, was very spacious and it had extremely clean spaces. The view in the back off of the deck was very serene and soothing. It was located near several great restaurants and coffee shops. Denise was extremely kind and responsive during our stay ad well. I would recommend this Airbnb to anyone traveling to the area very highly.

Irish Retreat
We stayed at Linda’s while visiting family over the holidays and it was a comfortable, well stocked, clean, home away from home. It’s on a busy road but because of that close to everything. Linda was responsive and helpful. Kitchen had lots of condiments, coffee filters, cooking basics. Lots of extras like blankets, games, and box fans.

Pure Michiana - Rustic & Cozy - near the stateline
Great experience all the way around as always

Relaxation in the country close to everything
Great place to stay for ND Football games, we'l be back next year!

5 Bedroom House "Quiet Street right off the Lake"
Lence’s house was perfect for us while we were in town visiting with family. There were 9 of us, and the way the bedrooms were set up allowed for plenty of privacy. Everything was clean and new feeling. We have stayed in several houses in Culver over the years and this has been one of the nicest we have stayed at. We will definitely try to stay here next time we are in town.

Serene Settings
A hidden gem! Perfect hideaway for city and country folks alike.
Quick stats about house rentals in Chesterton
Total rentals
40 properties
Nightly prices starting at
£53 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
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- Family-friendly rentals Chesterton
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- 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
- Lincoln Park Zoo
- Museum of Science and Industry
- The Field Museum
- Wicker Park
- Chicago History Museum
- Willis Tower
- Potato Creek State Park
- Flossmoor Golf Club
- Brookfield Zoo
- Lincoln Park
- Garfield Park Conservatory
- Chicago Cultural Center
- Promontory Point