Chicago Grayland Station Vacation Rentals

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Browse Select Chicago Grayland Station Vacation Homes

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (50)
"This is a really cute property close to a lot of neighborhood restaurants and bars. The host is really nice and even moved his car for us so we could have his spot when we arrived. We would definitely stay here again. "
Great 3 bedroom rental unit near Logan Square

Historic 1920s Private Bungalow Near Logan Square!

9.8 out of 10, Exceptional, (39)
"Could not have been happier with this property! Everything was great!"
Historic 1920s Private Bungalow Near Logan Square!

Pulaski Mahal - Spacious 3bed/2.5bath with Game Room. Close to Hwy, train.

10.0 out of 10, Exceptional, (8)
"I've been fortunate to stay in VRBO rentals abroad and in the US over 20 times, and though I've only had good experiences, this was easily the best. Raminder is an attentive and communicative host, stocking the kitchen with more drinks and snacks than we could eat. He's answers texts quickly and is very easygoing. The townhouse is well equipped, and the basement game room is amazing: ping pong table, Foosball, darts and games. There's plenty of living space for a large group (we were six) to...
Pulaski Mahal - Spacious 3bed/2.5bath with Game Room. Close to Hwy, train.

Single Family Home with 3 Bedrooms + Attic with 2 beds

10.0 out of 10, Exceptional, (3)
"Like the property very much."
Single Family Home with 3 Bedrooms + Attic with 2 beds

Gorgeous NEW 5 BDR/ 4BA in Logan Square w/Parking!

9.2 out of 10, Wonderful, (46)
"Overall our stay was so so great! The area of the house was nice, quiet and safe. One thing I would say is that there were ants so we had to make sure to not leave anything around. The host was very responsive and helpful! Other than that the city was close by and there was a lot of shops/ restaurants walking distance too. "
Gorgeous NEW 5 BDR/ 4BA in Logan Square w/Parking!

Chic 3BR King Bed+Work-Friendly+ Firepit

Chic 3BR King Bed+Work-Friendly+ Firepit

Stunning 4-Bed 4-Bath Home - Prime Location OHare & Downtown <25-min, Free PRKNG

2.0 star property
10.0 out of 10, Exceptional, (1)
"Extremely nice place to stay! The neighborhood is quiet with a lot of great restaurant choices within walking distance! Very easy to navigate around the neighborhood too! The host, Toby, is very easy to communicate with and quick and concise with his responses and descriptions. Would definitely book again for similar trips!"
Stunning 4-Bed 4-Bath Home - Prime Location OHare & Downtown <25-min, Free PRKNG

Stunning New 6 Bedroom Home w/ Parking in Chicago (Superhosts)

9.0 out of 10, Wonderful, (19)
"Nice, quiet neighborhood with garage parking. Lots of room and Jeff said he would stay here again!!"
Stunning New 6 Bedroom Home w/ Parking in Chicago (Superhosts)

Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!

9.8 out of 10, Exceptional, (6)
"This home worked out perfect for us! Our cosmetology students had a great first trip to Chicago! Thank you!"
Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!

Stylish 6 Bedroom Home in Trendy Logan Square!

9.8 out of 10, Exceptional, (53)
"East access to everything we needed, was the perfect size for a large group to move around easily. Would recommend"
Stylish 6 Bedroom Home in Trendy Logan Square!

BoHo House - A Chic, 1903 Chicago Workers Cottage

10.0 out of 10, Exceptional, (13)
"Highly recommend this property! It’s close to everything, our dog felt at home, and communication with the property owner was top notch! We will definitely stay here again when we find ourselves in Chicago next."
BoHo House - A Chic, 1903 Chicago Workers Cottage

The Logandale: HUGE Mid-Century Home, sleeps 15

9.4 out of 10, Exceptional, (3)
"We had a wonderful stay for a 14 person bachelorette party! Chic property with enough room for everyone, difficult to find in Chicago. Very modern and new updates, easy uber ride to many parts of the city, very close to Logan Square! Would recommend!"
The Logandale: HUGE Mid-Century Home, sleeps 15

Game Room, Deck & Yard: Chicago Home

2.0 star property
Game Room, Deck & Yard: Chicago Home

5 Star Epicurean Experience with Hip, Modern, Gazebo with BBQ Grill & Sleeps 14.

10.0 out of 10, Exceptional, (8)
"We had a great time and accommodations were great as well."
5 Star Epicurean Experience with Hip, Modern, Gazebo with BBQ Grill & Sleeps 14.

Elegant 3-Bed, 3-Bath Home in Chicago <25-minutes to O’Hare & Downtown + Parking

9.6 out of 10, Exceptional, (4)
"The property was very nice and comfortable. Nice location in a quite neighborhood. Plenty of space for 8 adults."
Elegant 3-Bed, 3-Bath Home in Chicago <25-minutes to O’Hare & Downtown + Parking

Irving Park/Avondale Updated Vintage Top Unit in 2-Flat

10.0 out of 10, Exceptional, (2)
"I stayed here with my adult sons and it was fantastic. Very clean, within walking distance to good restaurants and coffee as well as train and bus lines. We loved it!"
Irving Park/Avondale Updated Vintage Top Unit in 2-Flat

Luxury Charming 3-bedroom house with WiFi, AC in enjoyable Chicago

Luxury Charming 3-bedroom house with WiFi, AC in enjoyable Chicago

LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!

10.0 out of 10, Exceptional, (38)
"Well appointed place and in a good location. Parking pass works great!"
LOGAN SQUARE: Chic, Comfy 1st Floor 2 BDRM APT! Parking Incld!

Easy city living 2 bed 2 bath with private patio

Easy city living 2 bed 2 bath with private patio
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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Top Chicago Grayland Station Hotel Reviews