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Check prices for these dates

Next weekend
14 Rab. I - 16 Rab. I
In two weeks
21 Rab. I - 23 Rab. I
In one month
4 Rab. II - 6 Rab. II
In two months
2 Jum. I - 4 Jum. I

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

'Summer Breeze' Lakeside Condo - Walk to Town & Marina + POOL
Beach nearby, sun loungers, beach towels

'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
Outdoor dining

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!
Beach

(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
Property grounds

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
Property grounds

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!"
Lake retreat with unique dome near Indiana Dunes
Idyllic New Buffalo Condo: Walk to Beach & Shops!
Fridge, microwave, stovetop, dishwasher

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
Point of interest

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
Fridge, microwave, oven, stovetop

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
Miscellaneous

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.
Property grounds

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.
A SKYLINE LAKE VIEW: Top-floor downtown condo with pool, gym and more
Fridge, microwave, oven, stovetop

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
King Bed Suite | Indoor Pool. Free Breakfast.
Fridge, microwave, stovetop, dishwasher

King Bed Suite | Indoor Pool. Free Breakfast.

King Bed Suite | Indoor Pool. Free Breakfast.
(2025 Open!) New Buffalo Condo With Association Pool & Hot Tub!
Beach nearby

(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!
Microwave, stovetop, dishwasher, coffee/tea maker

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!
Beach

(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.
Fridge, microwave, stovetop, dishwasher

Free Breakfast. Indoor Pool. Gym. Business Center.

Free Breakfast. Indoor Pool. Gym. Business Center.
Corporate Short Term Rental In Northwest Indiana
Private kitchen

Corporate Short Term Rental In Northwest Indiana

Corporate Short Term Rental In Northwest Indiana
2 Bedroom | Free Daily Breakfast. Indoor Pool.
Fridge, microwave, stovetop, dishwasher

2 Bedroom | Free Daily Breakfast. Indoor Pool.

2 Bedroom | Free Daily Breakfast. Indoor Pool.
Merrillville Condo-Close to Hospitals and Refinery
Fridge, microwave, oven, stovetop

Merrillville Condo-Close to Hospitals and Refinery

8.0 out of 10, Very Good, (1)
"Was a nice stay. Clean and comfy. Both beds are comfortable and had nice pillows and blankets. The kitchen has all the supplies needed to cook and eat. A washer and dryer are in the unit. Has a smart tv so you can log into your own netflix account or tv apps. The neighborhood is interesting. Becky was very helpful. My son forgot his favorite stuffed animals and she let me know right after checkout and had them ready for me to grab quickly when I turned around. Thank you again Becky!"
Merrillville Condo-Close to Hospitals and Refinery
Chicagoland/Northwest Indiana Corporate Condo Travel Nurses /Oil Refinery
Fridge, microwave, oven, dishwasher

Chicagoland/Northwest Indiana Corporate Condo Travel Nurses /Oil Refinery

Chicagoland/Northwest Indiana Corporate Condo Travel Nurses /Oil Refinery
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.
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Other property types in Chesterton

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

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

10.0 out of 10, Exceptional, (83)
"Our stay at this Vrbo was absolutely incredible! The home was cozy, very clean, and had everything we needed for a relaxing getaway. The large windows offered breathtaking views of Lake Michigan, and even though the lake was partially frozen, it was still beautiful to see. The peaceful winter scenery made our stay even more special.The location was perfect—just a short drive to plenty of hiking trails, which were not only stunning but also very dog-friendly! Our pup loved exploring alongside us,...
The price is SAR 750
SAR 1,201 total
includes taxes & fees
4 Mar - 5 Mar
Cabin 53 steps from Porter Beach on Lake Michigan: Family & Pet-Friendly
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Beach nearby

Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes

9.0 out of 10, Wonderful, (50)
"I booked this stay as a birthday gift for my son. He and his fiancé stayed for 2 nights/3 days. They absolutely enjoyed there stay. The place was clean and just like the pictures displayed. They had an issue with the code not working to enter the property, Don the host got in touch with us immediately and even refunded some money for the inconvenience! I will definitely be booking again for my daughters birthday!!"
The price is SAR 296
SAR 416 total
includes taxes & fees
4 Mar - 5 Mar
Private Downtown Apt, King Bed, Jet Bath, Fireplace, Grill, near Indiana Dunes
Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes
Fridge, microwave, oven, stovetop

Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes

9.8 out of 10, Exceptional, (51)
"This quaint house was perfectly located for attending the Trojan Classic showchoir competition. Plenty of room and nicely equipped. Though it was too cold to use the backyard it looked very nice."
The price is SAR 266
SAR 1,089 total
includes taxes & fees
10 Mar - 11 Mar
Dunes Home 3 Bedroom I 2 BHR I 2 Living rooms Home | Valpo University | Dunes
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

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