House holiday rentals in Chesterton

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Chesterton

House rentals with a pool

Superhost
Home in Bridgman
5 out of 5 average rating, 4 reviews

The Poolside Escape | Hot Tub | Arcade | Ping Pong

DanteRating, 5 stars4 months ago
Had a great stay. Was great with communicating when needed.
Superhost
Home in Michigan City
4.92 out of 5 average rating, 107 reviews

Beautiful home with Beach views in Beachwalk

SamanthaRating, 5 stars6 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 favourite
Home in Michigan City
4.97 out of 5 average rating, 174 reviews

5 Bedroom Luxury Home In Heart of Beachwalk Resort

JeffRating, 5 stars4 days 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
Guest favourite
Home in Chesterton
4.98 out of 5 average rating, 40 reviews

Pool House near the Indiana Dunes

KrishnaRating, 5 stars7 months ago
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!
Top guest favourite
Home in Union Pier
4.96 out of 5 average rating, 146 reviews

New Hot Tub Community pool Union Pier

Maria GuadalupeRating, 5 stars1 week ago
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.
Guest favourite
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.
Superhost
Home in Three Oaks
4.88 out of 5 average rating, 120 reviews

Luxury Living in Harbor Country|Hot Tub| Sleeps 10

PranjalRating, 5 stars1 month ago
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!
Guest favourite
Home in South Bend
4.92 out of 5 average rating, 284 reviews

Pool | Hot Tub | Backyard Oasis | Game Room | Fun

MosheRating, 5 stars2 weeks ago
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

Guest favourite
Home in Berrien Springs
4.94 out of 5 average rating, 125 reviews

18 acres | Arcades | Heated Pool | Hot Tub | Pond

MarianaRating, 5 stars1 week ago
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.
Superhost
Home in Miller
4.81 out of 5 average rating, 58 reviews

Indiana Dunes Park Getaway w/Firepit, Near Beach

NicholasRating, 5 stars8 months ago
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!
Guest favourite
Home in Three Oaks
5 out of 5 average rating, 20 reviews

It's A Dog's Life

JennaRating, 5 stars3 months ago
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!!
Guest favourite
Home in Michigan City
4.98 out of 5 average rating, 61 reviews

Picture Perfect Lake House Steps from the Beach

SoniaRating, 5 stars6 months ago
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!
Top guest favourite
Home in New Buffalo
4.96 out of 5 average rating, 154 reviews

In-town Lovely Home! Steps to Starbucks & Beach!

JeffRating, 5 stars1 month ago
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!
Superhost
Home in South Bend
5 out of 5 average rating, 4 reviews

Long-Term Spacious House for Rent

MaureenRating, 5 stars4 months ago
Ruthanne was beyond helpful and attentive.
Guest favourite
Home in South Bend
4.88 out of 5 average rating, 154 reviews

3BR w/sauna, tanning bed, hot tub 3.9 miles fromND

ShikaRating, 5 stars2 weeks ago
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.
Guest favourite
Home in South Bend
4.97 out of 5 average rating, 37 reviews

Sleeps 15, 7 bedrooms, 4 baths, 2 kitchens

CharleneRating, 5 stars4 months ago
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

Superhost
Home in Michigan City
4.85 out of 5 average rating, 52 reviews

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

LeslyRating, 5 stars6 months ago
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 !
Guest favourite
Home in Benton Harbor
4.84 out of 5 average rating, 83 reviews

Serenity House on the River

GillianRating, 5 stars1 week ago
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.
Guest favourite
Home in La Porte
4.97 out of 5 average rating, 86 reviews

Renovated french country lake home. 6bedroom/4bath

AaronRating, 5 stars2 months ago
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.
Guest favourite
Home in South Bend
4.86 out of 5 average rating, 166 reviews

Irish Retreat

MicheleRating, 5 stars4 months ago
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.
Top guest favourite
Home in Rolling Prairie
4.96 out of 5 average rating, 195 reviews

Pure Michiana - Rustic & Cozy - near the stateline

MikeRating, 5 stars2 weeks ago
Great experience all the way around as always
Guest favourite
Home in South Bend
4.86 out of 5 average rating, 58 reviews

Relaxation in the country close to everything

JustinRating, 5 stars5 months ago
Great place to stay for ND Football games, we'l be back next year!
Guest favourite
Home in Culver
5 out of 5 average rating, 6 reviews

5 Bedroom House "Quiet Street right off the Lake"

MeganRating, 5 stars9 months ago
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.
Guest favourite
Home in Valparaiso
4.96 out of 5 average rating, 26 reviews

Serene Settings

JoeRating, 5 stars2 weeks ago
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

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