Condo vacation rentals in Michigan City

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Top-rated condo rentals in Michigan City

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Guest favorite

Condo in Chicago

4.92 out of 5 average rating, 110 reviews

Stunning, Spacious, & Sun-Soaked 1br Uptown Condo

Perfect for any type of traveler, my bright and inviting one bedroom condo in Uptown is a sanctuary stocked with every amenity you could need! There's an organized workspace area if you bring your work with you to Chicago, a gorgeous sunroom with a sofa bed, and a beautiful kitchen stocked with everything you could need to whip up a delicious meal. Steps to the lakefront and Montrose Beach and just a 6-minute walk to the Wilson Red Line, you can't beat this location. Book today! Welcome!

Apr 1 – 8

G$59,212 GYD per night

Guest favorite

Condo in Chicago

4.9 out of 5 average rating, 235 reviews

MAG MILE 2/2 Gold Coast Gem (+Parking/Rooftop)

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach - Walk to every popular attraction that makes Chicago so great! - Parking spot on-site with in/out access!! - Newly remodeled interior - Tranquil rooftop overlooking Lake Michigan - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Amazing views of Lake Michigan We look forward to hosting you!

May 10 – 15

G$84,009 GYD per night

Guest favorite

Condo in St. Joseph

4.9 out of 5 average rating, 115 reviews

*Luxury condo on water in St Joseph, 2 queen beds*

Modern and beautiful condo on the river going into the mouth of Lake Michigan near Silver Beach. Immediately next door to Clementine’s restaurant and within walking distance to many shops, bars, downtown, and the beach. Right next to Pier 33 Marina and docks and water rentals. You can eat, drink, fish, shop, and enjoy the beautiful scenery all at one spot! The condo also has a rooftop for corn hole games, a grill, and tanning. Silver beach/the pier is literally a short walk away!

Feb 11 – 18

G$40,402 GYD per night

Guest favorite

Condo in Chicago

4.96 out of 5 average rating, 178 reviews

Updated Designer Duplex In Fulton Market W/parking

UPDATE: We just completed our luxury renovation March 2023! New kitchen, bathrooms, and patio with a firepit. We hope you enjoy! The first thing you notice stepping into my house are the sky-high ceilings! Enormous floor to ceiling windows allow light to stream into the the 2 floor home. The stylish and very large terrace are great for summer nights. Walk out the front door & you are in the heart of restaurant row with all the best bars and restaurant in the city. Parking included!

Mar 3 – 10

G$166,269 GYD per night

Guest favorite

Condo in Chicago

4.91 out of 5 average rating, 246 reviews

Old Town Pied-à-Terre w/Pvt Terrace and Parking

Our bright modern 2 bedroom condo has 13 ft ceilings and an amazing private terrace. It's in the heart of Old Town, right on Wells St - steps outside the door are some of the city's best restaurants, cafes, and bars. Just a 5 minute walk to two world-renowned comedy clubs: Second City and Zanies. The Chicago History Museum, Lincoln Park Zoo, and the lake are a quick walk too. The Sedgwick CTA stop is nearby too! Please note: patio cushions are available May through October.

Sep 8 – 15

G$120,772 GYD per night

Superhost

Condo in New Buffalo

4.8 out of 5 average rating, 142 reviews

Lake Condo in the heart of Downtown New Buffalo

Covid-19 safety enhanced cleaning certified! AMAZING LOCATION steps away from New Buffalo beach! Be near all the action in this lovely and spacious 2br condo! Breweries, restaurants, shopping, Amtrak & Grocery all within 2 blocks. Located right on Whittaker Street in the heart of downtown New Buffalo. This unique condo is a stand alone unit above a storefront so guests will have privacy and peace. Washer/Dryer in unit along with a full kitchen and private patio.

Nov 24 – Dec 1

G$31,275 GYD per night

Guest favorite

Condo in Chicago

4.98 out of 5 average rating, 201 reviews

Near Lake Michigan & Wrigley Field

Available 2B/2B condo with 2 King Size Beds. One block from the Aragon Ballroom and Riviera with great views of Uptown and two blocks from Lake Michigan. It’s also a perfect place to stay if your in town for a Cubs game. You can see the stadium from the rooftop deck. Walking distance to everything you need, 2 train stations, groceries, gym, restaurants/ bars. The perfect place to come and go as you please with easy key code entry.

Sep 19 – 26

G$68,149 GYD per night

Guest favorite

Condo in Chicago

4.99 out of 5 average rating, 561 reviews

Urban Comfort in the Heart of Chicago

Proud to be amongst the highest rated listings in the city. This is the PRIVATE first floor of our duplex condo, with your own entrance/exit, 75" flatscreen TV, central heat/air, and an en-suite bathroom. We are in the middle of Chicago's vibrant Northside while still having the benefit of coming home to a tree lined one lane residential street. Please contact us with any questions at all before you book your stay.

Jun 24 – Jul 1

G$50,190 GYD per night

Guest favorite

Condo in Chicago

4.99 out of 5 average rating, 212 reviews

❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D

• 1,750ft² / 162m² • Walk Score 95 (walk to cafe's, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Onsite, secured parking • Onsite washer + dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport Note: The wood burning fireplace is not operational.

Mar 16 – 23

G$88,501 GYD per night

Guest favorite

Condo in Chicago

4.98 out of 5 average rating, 281 reviews

Sunny Apartment Just 2 Blocks from Wrigley and Boystown

Located on a quiet, tree-lined street, the apartment sits on the second storey of a classic Chicago house in Lakeview—a vibrant lakefront community with arts and culture, green space, eateries, boutiques, nightlife, and transportation options. Street parking passes available upon request. Less than five minute walk to red line El (subway train) stop and several bus lines.

Aug 16 – 23

G$91,316 GYD per night

Guest favorite

Condo in Portage

4.8 out of 5 average rating, 158 reviews

Marina Condo near Lake Michigan

Enjoy the marina lifestyle in the best kept secret on Lake Michigan at Marina Shores. Only 45 minutes from downtown Chicago. A short walk to the South Shore Line train station to Chicago, Michigan City or South Bend. Note, you will hear train noise. This recently updated condo is the perfect place for your visit.

Jan 18 – 25

G$29,498 GYD per night

Guest favorite

Condo in Elkhart

4.93 out of 5 average rating, 127 reviews

Experience Main Street

Enjoy this high-end downtown condo and experience city-life with the feel of big-city but nestled in a quaint small town atmosphere. Suitable for business executive trips, wedding guests, Notre Dame events, or just a weekend get-away.

Dec 2 – 9

G$40,533 GYD per night