Vacation rentals in Chesterton

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Popular amenities for Chesterton vacation rentals

Stay near Chesterton's top sights

Chesterton’s European Market20 locals recommend
Lucrezia® Café20 locals recommend
Wagner's Ribs19 locals recommend
Running Vines Winery18 locals recommend
Octave Grill18 locals recommend
Indiana Dunes National Lakeshore Visitor Center12 locals recommend

Other great vacation rentals in Chesterton

Superhost
The exterior view reveals a two-story home with a light blue facade and a vibrant red front door. Outdoor verandas are present on both levels, adorned with hanging plants. A well-maintained garden surrounds the home, featuring various greenery and flowers, and offers a welcoming entry.
Home in Michigan City
5 out of 5 average rating, 4 reviews

Lake Life Livin’- Beach House

ChristineRating, 5 stars6 months ago
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 .
Superhost
An inviting backyard features a central fire pit surrounded by several metal chairs. The bi-level house is visible in the background, with large windows reflecting the evening light. A hot tub is seen nearby, framed by trees and a spacious lawn.
Apartment in Bridgman
4.79 out of 5 average rating, 106 reviews

Relax - SW Mi Getaway/Hot Tub-Beaches & Wine Tours

BernadetteRating, 5 stars1 month ago
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.
Guest favorite
A circular arrangement of colorful Adirondack chairs is set in a lush green lawn. The seating area is shaded by surrounding trees, creating a relaxed outdoor space for gatherings. A small table is positioned at the center, enhancing the inviting atmosphere.
Home in Berrien Springs
4.95 out of 5 average rating, 123 reviews

Great Living Too

MichelleRating, 5 stars2 months ago
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!
Guest favorite
An inground swimming pool features clear, blue water surrounded by a spacious deck area. Several lounge chairs are arranged alongside the pool, and pool floats are visible in the water. A secure fence encloses the area, providing safety and privacy.
Home in Michigan City
4.92 out of 5 average rating, 64 reviews

Home near the lake with an inground pool

FreddieRating, 5 stars2 months ago
Clean house and will definitely book again for our needs. Very comfortable with everything.
Top guest favorite
The exterior of the estate is showcased, featuring a combination of natural stone and dark siding. Large glass windows enhance the entryway, framed by a geometric roofline. Lush greenery surrounds the property, with tall trees and well-maintained shrubs providing a serene ambiance.
Vacation home in Baroda
4.94 out of 5 average rating, 17 reviews

Location location

GabrielRating, 5 stars1 month ago
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.
Top guest favorite
Cottage in Union Pier
4.96 out of 5 average rating, 200 reviews

Designer Cottage Relax Beach Pool & Spa—Windjammer

SarahRating, 5 stars2 weeks ago
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
Guest favorite
Home in Union Pier
4.96 out of 5 average rating, 114 reviews

cozy new buffalo cabin, hot tub, 14m walk to beach

TimothyRating, 5 stars1 month ago
very fun relaxing experience, stayed in the back cabin. great time
Guest favorite
A wooden staircase descends towards a calm lake beach with gentle waves lapping at the shore. Lush greenery frames the steps, and the expansive water reflects soft pastel colors from the sky, creating a serene atmosphere.
Cottage in New Buffalo
4.97 out of 5 average rating, 32 reviews

Sprawling Retreat w/ Private Beach Access!

CookieRating, 5 stars4 months ago
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.

Destinations to explore

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