
Vacation rentals in Chesterton
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Top-rated vacation rentals in Chesterton
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Chesterton vacation rentals
Other great vacation rentals in Chesterton

Lake Life Livin’- Beach House
We had the greatest girls weekend here . House is cozy, decorated beautifully, well appointed with everything you could need. Walkable to beach & a fun breakfast restaurant. Spacious common areas. Large bedrooms. Great backyard with comfortable , nice furniture and a fire table. Cozy front porch with comfortable seats . Lots of seating in the house . Huge kitchen with every utensil, bowl, plate or cup you may need . Host was very responsive to all of our questions .

Relax - SW Mi Getaway/Hot Tub-Beaches & Wine Tours
Was an absolutely relaxing stay. It was exactly what my husband and I were looking for. An extended weekend away with a bunch of things around us to do. It had a little bit of everything around us, including privacy. It was fantastic.

Great Living Too
I cannot say enough about how clean the house was. Wonderful space for everyone. Kitchen table was large enough for my group to play games at and the basement space was large enough for everyone too! If we are back in the area we would stay here again!

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

Location location
I don’t think the pictures do this house any justice. House is tremendously big. Lots of space for large families. The views? Amazing. With the vineyard next door and the woods surrounding it, it was a great view. Very ample parking. Easy to find and close to the highway. There’s plenty of wineries near the house. Also grocery stores for any quick essentials. Back to the house. Very clean and big kitchen. Has everything you need from plates to cups. The living room is big. Tv is huge to keep the kids entertained. It was a little chilly so we stayed inside. But the deck looks really new and big with a girl. The backyard was huge. Rooms were big with nice beds and clean as well. All bathrooms were super clean and big. Basement had an entire other living area with rooms as well. Pool table kept everyone entertained. Dining room had a nice table for the large family dinners. In conclusion, I will definitely love to book this for the summer. You won’t regret it.

Designer Cottage Relax Beach Pool & Spa—Windjammer
Birthday brownies upon arrival! Great quiet location but very convenient for local shops and restaurants. Can walk to the beach! Can’t wait for the opportunity to visit again

cozy new buffalo cabin, hot tub, 14m walk to beach
very fun relaxing experience, stayed in the back cabin. great time

Sprawling Retreat w/ Private Beach Access!
I had my family of 17 up to MI for this past Thanksgiving. I own a home about 100 yards from Monika’s and half my family stayed there. It was incredibly convenient and my family loved the house! Coffee in the sunroom, hot tubbing and hanging at the fire pit with a roaring fire. Heaven!!
Quick stats about vacation rentals in Chesterton
Total rentals
50 properties
Nightly prices starting at
$10 before taxes and fees
Total number of reviews
4.3K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Chesterton?
Yes! Work meets play with ease at over 30 vacation rentals in Chesterton featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Chesterton?
Four-legged friends are welcome in Chesterton. Choose from more than 20 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Chesterton?
Experience the best of Chesterton with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there Chesterton vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Chesterton, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Chesterton have wifi?
Absolutely! We offer over 40 house rentals with wifi in Chesterton. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Chesterton?
Chesterton has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
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- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Warren Dunes State Park
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Humboldt Park
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- Museum of Science and Industry
- Chicago History Museum
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- The Field Museum
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- Wicker Park
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- Garfield Park Conservatory
- Lincoln Park
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