Holiday Homes in East Chicago

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Featured Holiday Homes in East Chicago

Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

10.0 out of 10, Exceptional, (4)
"This is a very nice property in an up and coming neighborhood. The house is multilevel with three spacious bedrooms (two with ensuite bathrooms). As a bonus, the house has a garage opening onto an alleyway. Everything was very clean, bright and well appointed. The property is located in an up and coming neighborhood very convenient to good el lines and only a couple of blocks from a wonderful coffee place we used every day during our stay. Everything with the property went well and we would stay...
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

9.4 out of 10, Exceptional, (81)
"This property worked well for our group of 14. The need to go outside to get between the upper and lower levels had been made very clear. It was a bit tricky at first with 5 young children, but we all adjusted pretty quickly. The lower level is more basic than upstairs but still worked very well for 5 of the group. The neighborhood was perfect for the location of the wedding we were attending, and having garage parking was fantastic. Definitely recommend."
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Crestwood Gem! Family and pets friendly 3-bedroom house with WiFi, AC

2.0 star property
10.0 out of 10, Exceptional, (2)
"So cute and lots of space. Would definitely stay here again!"
Crestwood Gem! Family and pets friendly 3-bedroom house with WiFi, AC

Cozy Home Sweet Homewood.

10.0 out of 10, Exceptional, (15)
"We were in Homewood for a wedding and this was a perfect location. Besides its proximity to the wedding venue, we walked to the train station for a day in the city. The house is exactly as listed. It was very clean, organized and comfortable. Everything we needed was supplied. My husband especially liked the TVs. 😊 Since we were there on Halloween, we had the added bonus of seeing a truly family-oriented neighborhood in action. Lots of happy trick-or-treaters showed up accompanied by lots of...
Cozy Home Sweet Homewood.

Luxury Chicago TH is a 10-minute drive to DWTN, perfect for city access RSV Now

9.6 out of 10, Exceptional, (9)
"Stayed at the property for a conference at McCormick. Very convenient and nice."
Luxury Chicago TH is a 10-minute drive to DWTN, perfect for city access RSV Now

Nestled just behind Marquette Park. 5 minute walk to beach.

10.0 out of 10, Exceptional, (9)
"Could not be more thankful for her prompt replies and accommodations."
Nestled just behind Marquette Park. 5 minute walk to beach.

Luxury 3-bedroom house in Northern Indiana with new EVERYTHING!

10.0 out of 10, Exceptional, (4)
" The home was very clean. The host was very helpful and easy to communicate with. My family enjoyed our stay."
The price is AU$438
includes taxes & fees
4 Dec - 5 Dec
Luxury 3-bedroom house in Northern Indiana with new EVERYTHING!

Villa Gold Cost -Sleeps 12+KING Bed-Pets-Garage- 65”TV Netflix-Wifi-Ping Pong

10.0 out of 10, Exceptional, (2)
"We absolutely loved this place! It is gorgeous inside - the pics don’t do it justice. Communication with the host was super responsive too. Highly recommend!"
Villa Gold Cost -Sleeps 12+KING Bed-Pets-Garage- 65”TV Netflix-Wifi-Ping Pong

"The Nook"- ROOMY Home 2mi- Dunes & Chesterton, Yard, Fire Pit, Grill, Game Room

10.0 out of 10, Exceptional, (64)
"We had a great time. Very comfortable and plenty of room for to spread out. We enjoyed the game room and we even road the bikes. stt location."
"The Nook"- ROOMY Home 2mi- Dunes & Chesterton, Yard, Fire Pit, Grill, Game Room

Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

9.2 out of 10, Wonderful, (7)
"The house was good, plenty of space. The steps were hard to get up and down but the upstairs was a nice space. House had a bit of a musty odor and the windows could use a cleaning. One night while watching a movie, we received a text stating we were had a loud party and to keep it down. They must have big brother watching us as the only party going on that night was in the movie. Overall the house was close to the city but in a nice Neiborhood. Having a fenced yard with off street parking...
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

10.0 out of 10, Exceptional, (87)
"The house was simply beautiful, and the hosts were very communicative and on top of things. Would stay here again"
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

8.6 out of 10, Excellent, (4)
"Overall it was a great experience and I’ll be coming back sooner"
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

Full Luxurious Modern House Near Chicago

2.8 out of 10, (5)
"I stayed in this home for two nights. It was cold as ever. The heat did not work at all, no matter how high I turned it up and I couldn’t even heat up my food in the microwave because that didn’t work either. My food was not getting warm no matter how long I put it on in the microwave me and my company was cold For both nights."
Full Luxurious Modern House Near Chicago

Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

8.2 out of 10, Very good, (20)
"We really love the home and the setup."
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

Dreamsville Gateway to Indiana Dunes National Park

6.0 out of 10, (1)
"Listed as private home , once you get there and read the house rules it states shared refrigerator with owner. Owner comes in while you are gone and turns off all lights and the Ac, even goes into your locked room to turn off ac."
Dreamsville Gateway to Indiana Dunes National Park

Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

9.2 out of 10, Wonderful, (56)
"We recently rented this home for our church's women's fall spiritual retreat. This stay for our group of 21 ladies was more than we expected. We chose this home for its size, proximity to the shore, and great accommodations. Upon our arrival we were pleasantly surprised to find the house had been recently updated. It was absolutely beautiful...bright, serene, and peaceful! The cleanliness of the home was great! The attention to detail was appreciated. I love a well stocked kitchen and this...
Spa-quality amenities, dog friendly, close to trails, IN Dunes Nat’l Park

Prime location Historic Chicago Townhouse

9.4 out of 10, Exceptional, (63)
"It was great to stay in a beautiful grey stone in Gold Coast. Better yet it is located in an excellent area, less than 1/4 mile walking distance to the lake, around the corner from Michigan Avenue shopping, the Hancock Building, the Drake, Lou Malnati's and other great restaurants, and pharmacy-- we walked to all of these places! It felt like a home away from home with the layout of the home and nice neighborhood. It was stocked up with everything one needs in the kitchen, bathrooms, bedrooms...
Prime location Historic Chicago Townhouse

Blue Birdhouse by the Beach

9.2 out of 10, Wonderful, (21)
"We had a fantastic stay at the Blue Birdhouse. Super close to the beach and a very clean little house. Wagners Ribs were walking distance away and delicious food. We had an issue accessing the house that the owner quickly resolved. Great little place. "
The price is AU$387
includes taxes & fees
2 Dec - 3 Dec
Blue Birdhouse by the Beach

The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

9.8 out of 10, Exceptional, (8)
"Would reserve this again wonderful host"
The price is AU$173
includes taxes & fees
3 Dec - 4 Dec
The "Pool Barn Camper" w/Hot Tub near Indiana Dunes

Newly Renovated with Finished Basement

9.8 out of 10, Exceptional, (73)
"My 3 girlfriends and I enjoyed staying at this spacious comfortable clean home. We would love to visit again when we are back visiting the Portage area. Thank you!"
The price is AU$471
includes taxes & fees
2 Dec - 3 Dec
Newly Renovated with Finished Basement
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 East Chicago

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (592)
"Staff is friendly and very helpful!"
The price is AU$239
includes taxes & fees
8 Dec - 9 Dec
Sentral Michigan Avenue

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (208)
"Easiest check in and check out process "
The price is AU$145
includes taxes & fees
24 Dec - 25 Dec
Sonder Market Hall

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (395)
"Nice"
The price is AU$258
includes taxes & fees
23 Dec - 24 Dec
Sonder South Wabash
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.
Beautiful view of the beach with palm trees

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