Search Condo Rentals in Chesterton

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month

Compare 23 Condo Rentals in Chesterton with updated reviews, rates, and availability.

'Summer Breeze' Lakeside Condo - Walk to Town & Marina + POOL

10.0 out of 10, Exceptional, (113)
"Property just as advertised. Clean and easy to access. Great location. I would stay again"
'Summer Breeze' Lakeside Condo - Walk to Town & Marina + POOL

Luxury Waterfront 2 Bedroom Condo by Lake Michigan

10.0 out of 10, Exceptional, (13)
"We liked how clean and well decorated the condo was. The pool was nice, and the train close by was a bonus. We went to Indiana Dunes national park and to Chicago during our stay."
Luxury Waterfront 2 Bedroom Condo by Lake Michigan

(2025 Open/3 NT Min) Condo in the Heart of New Buffalo with Heated Pool!

9.6 out of 10, Exceptional, (23)
"The condo is wonderful, more spacious than pictures give it credit for and close to everything New Buffalo has to offer. Perfect long weekend getaway with our two small kids, enjoying the beaches, dunes, shops, outdoor (and indoor) pools and walkable dining. We'll definitely stay here again!"
(2025 Open/3 NT Min) Condo in the Heart of New Buffalo with Heated Pool!

Serenity on the Shores - with easy transport to Chicago/SouthShore across the St

10.0 out of 10, Exceptional, (2)
"Just what we were looking for "
Serenity on the Shores - with easy transport to Chicago/SouthShore across the St

Lake retreat with unique dome near Indiana Dunes

2.0 star property
10.0 out of 10, Exceptional, (2)
"Nice spot, with nice scenery and area! Really enjoyed my stay there. Owner responded quickly everything! Would highly recommend this spot for a little getaway!"
The price is SAR 450
SAR 525 total
includes taxes & fees
23 Feb - 24 Feb
Lake retreat with unique dome near Indiana Dunes

Idyllic New Buffalo Condo: Walk to Beach & Shops!

9.8 out of 10, Exceptional, (37)
"We had a great stay, and the online listing accurately represented the property. Very clean, great size bedrooms/living area, and fantastic open concept. The pool is a walk out from the living room which could be very convenient during the summer. The only item to be aware of, is the train station is literally in your backyard by the bedrooms. Windows are decent soundproof, but you can hear it go by. We had two young kids, so they loved seeing the train go by, but for light sleepers, could...
Idyllic New Buffalo Condo: Walk to Beach & Shops!

3BR Condo Close To The Beach! In/OutDoor Pools

10.0 out of 10, Exceptional, (90)
"It was perfectly situated near the town's center. Very nicely appointed and very spacious bedrooms and kitchen/living room open room. We enjoyed our time there and would love to return next year."
3BR Condo Close To The Beach! In/OutDoor Pools

LAKE TIME @ NEW BUFFALO: Condo with private pool - walk to the beach

10.0 out of 10, Exceptional, (13)
"My family and I were very pleased with this condo in New Buffalo. So much space for our two kids to run around and everything is within walking distance. Will definitely stay again in the future! "
LAKE TIME @ NEW BUFFALO: Condo with private pool - walk to the beach

2025 OPEN Condo w/Marina Views Pools Walk to all Beach 1.5 blk

10.0 out of 10, Exceptional, (72)
"Perfect mid October weekend. Great weather, great times and great accomodations."
2025 OPEN Condo w/Marina Views Pools Walk to all Beach 1.5 blk

DOWNTOWN CONVENIENCE: Condo with private pool, Gym and close to everthing.

10.0 out of 10, Exceptional, (10)
"Great walkable location. Easy check in. We would visit again. "
DOWNTOWN CONVENIENCE: Condo with private pool, Gym and close to everthing.

BEACHSIDE GETAWAY: Condo with private pool and close to everthing.

10.0 out of 10, Exceptional, (15)
"My husband and our friends stayed a week and we could have stayed longer. This place was perfect, great location to everything downtown and the place was clean and had everything we needed. We enjoyed the pool and the patio so much. We would definitely come again."
BEACHSIDE GETAWAY: Condo with private pool and close to everthing.

A SKYLINE LAKE VIEW: Top-floor downtown condo with pool, gym and more

9.6 out of 10, Exceptional, (7)
"Condo was very comfortable, well stocked kitchen, very quiet location, can walk to shops, restaurants, and beach. Building very secure, parking easily accessible. Would definitely stay here again."
A SKYLINE LAKE VIEW: Top-floor downtown condo with pool, gym and more

HEART OF NEW BUFFALO: Downtown condo with private pool(s). Walk to everything.

9.8 out of 10, Exceptional, (7)
"Enjoyed our stay. Became acclimated to condo living rather then cottage. Convenient location and we walked to local restaurants and shopping."
HEART OF NEW BUFFALO: Downtown condo with private pool(s). Walk to everything.

King Bed Suite | Indoor Pool. Free Breakfast.

The price is SAR 963
SAR 1,214 total
includes taxes & fees
27 Feb - 28 Feb
King Bed Suite | Indoor Pool. Free Breakfast.

(2025 Open!) New Buffalo Condo With Association Pool & Hot Tub!

4.0 star property
9.2 out of 10, Wonderful, (24)
"The location of the property was great, and we enjoyed the community pool. Due to a recent storm, Google maps was giving us trouble finding the location. One of the people we spoke to for assist us was less than friendly but the other was nice. The property was nice and well kept. We did find sand all over the floor of the bottom bedroom as well as in that bed when we got there, there were popcorn kernels scattered in the living room rug and some of the roof deck furniture was covered in...
(2025 Open!) New Buffalo Condo With Association Pool & Hot Tub!

Charming New Buffalo Condo: Walk to Lake Michigan!

9.6 out of 10, Exceptional, (41)
"We had an absolutely amazing stay. This is our third time in New Buffalo and hope to stay at this exact location for years to come!"
Charming New Buffalo Condo: Walk to Lake Michigan!

(2025 Open!) Perfectly Located Buffalo Condo w/ Association Pool!

10.0 out of 10, Exceptional, (1)
"The communication with the property owner was great! We were missing a parking pass when we checked in, but the property owner quickly remedied the issue and a new pass was dropped off that Friday evening! The location was wonderful. The condo was walking distance to the main thoroughfare so access to shops and restaurants was easy! The bedroooms were a bit small but we made it work. Overall, good experience. I’d definitely stay there again."
(2025 Open!) Perfectly Located Buffalo Condo w/ Association Pool!

Free Breakfast. Indoor Pool. Gym. Business Center.

Free Breakfast. Indoor Pool. Gym. Business Center.

Corporate Short Term Rental In Northwest Indiana

Corporate Short Term Rental In Northwest Indiana

2 Bedroom | Free Daily Breakfast. Indoor Pool.

2 Bedroom | Free Daily Breakfast. Indoor Pool.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Chesterton
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Chesterton

Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

10.0 out of 10, Exceptional, (80)
"This cabin has an amazing views of Lake Michigan!! We loved our stay here...so peaceful and relaxing. The cabin was clean and the hosts provided lots of little extras (shampoo, bar soap, coffee pods). It is not a "luxury" feel....but everything is well maintained and very clean. We will definitely stay here again!!! "
The price is SAR 563
SAR 958 total
includes taxes & fees
31 Jan - 1 Feb
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly

The Neighborhood Hotel - Grand Beach

4.0 star property
9.4 out of 10, Exceptional, (39)
"Overall the place is wonderful and we enjoyed the amenities. My teenaged boys enjoyed the game room, pool at night, beach, fire pit. I loved the bed, having a kitchenette, and the coffeemaker. Much better than a typical hotel version. I’d caution using suite 10 for more than two people. The sleeper was what you’d expect a sleeper to be - not comfortable! The bed is amazing though. The bathroom could use more hooks for drying beachwear. I think instructions or information in general could be...
The Neighborhood Hotel - Grand Beach

BEACHFRONT LAKE MICHIGAN w/Lookout Tower & Lake Views - Sleeps 13

9.4 out of 10, Exceptional, (51)
"Christmas whit the family, nice view "
BEACHFRONT LAKE MICHIGAN w/Lookout Tower & Lake Views - Sleeps 13
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Why book your condo in Chesterton with Expedia?
Reserving a condo in Chesterton is as easy as entering your travel dates and picking an option that checks your boxes. After something luxurious or low cost, or a stay that also offers a kitchen? Use Expedia’s search filters to narrow your results even further and find the ideal fit.
How can I find cheap condos in Chesterton?
The simplest way to locate cheap condos in Chesterton is with Expedia’s useful filter tool. Narrow down your search by amenities, budget and star rating to discover awesome rates in a few clicks.