Photo by WanderingFunk009

Glencoe Holiday Rentals

Save an average of 15% on thousands of properties with Expedia Rewards

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide

Holiday Rentals in Glencoe

Outdoor pool
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, (198)
"This was an amazing place, in a great location, the view was unbelievable, and there was lots of things to do in the area our host, we’re great to work with, they had great insight, and information to share with us to make our stay even more enjoyable. we would definitely use their property again"
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Desk, iron/ironing board, WiFi, bed sheets
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
10.0 out of 10, Exceptional, (20)
"Very cool penthouse apartment with two balconies and access to additional rooftop patio having amazing views of the Chicago skyline. Highly recommend!"
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
Exterior
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, (7)
"Easy to check in, good information for parking in the area. The place was clean and nice."
The price is HK$646
per night
22 May - 23 May
Ground Floor Studios in Chicago by 747 Lofts
Save an average of 15% on thousands of hotels when you're signed in
Exterior
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
10.0 out of 10, Exceptional, (176)
"Great stay! All of the rooms were wonderful! Really close to food! There are a lot of stairs so make sure you are able to walk up but really great place!"
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
Lobby
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
10.0 out of 10, Exceptional, (2)
"very close to Michigan Avenue convenience store like a block away. It was a great stay."
The price is HK$1,281
per night
27 May - 28 May
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
9.8 out of 10, Exceptional, (28)
"Beautiful, spacious, clean rooms. Cozy safe neighborhood. Prompt and responsive communication. Would absolutely stay here again!!"
The Neighborhood Hotel-Little Italy
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (156)
"This is a fantastic location just outside of the city on a quiet street but close to everything. The Property Manager (Ross) is fantastic with communication and even after our flight was delayed three times, he met us at the door, gave us a thorough tour of where everything is located, and some great tips on where to eat. It's a $20 UBER to the heart of the city (Millenium Park) and the place is spotless! Highly recommend if you're looking for a place to hang your hat for a few days!"
Walking distance to restaurants, shops and Lake Michigan,
Property grounds
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (36)
"Great access to Wrigley/ South Port & Lake view neighborhoods. Very Clean and laid out space that maximizes the space in this unit. Will be back soon!"
Wrigley/Southport Corridor Garden Oasis +parking!
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (65)
"Very clean and comfortable. Great location very close to an L stop. Walkable to shopping and the lake front and river walk"
Kasa River North Chicago
Smart TV, books
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
9.6 out of 10, Exceptional, (7)
"Great unit! Spacious and clean. We were able to have the best family mini vacay sharing tons of laughs and memories. I believe it is family owned, which is a bonus for us. We even crossed paths with the grandmother who was very kind and accommodating. The only downside was that the neighborhood looked a bit rough in the harsh light of day. However, we only encountered polite neighbors and an adorable doggo next door."
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
Exterior
Cozy modern unit w/ easy access to downtown Chi
9.6 out of 10, Exceptional, (18)
"It’s really confortable clean and accesible easy"
Cozy modern unit w/ easy access to downtown Chi
Exterior
Chic Suite/Mins to L Train /Laundry/Free Parking
9.6 out of 10, Exceptional, (16)
"My wife and I spent a long weekend here. The apartment had plenty of room, was nicely decorated. The kitchen contained everything we needed to cook a full meal (which we did not). The bed is very comfortable. Ride service to downtown averaged $25. It was perfect."
The price is HK$625
per night
22 May - 23 May
Chic Suite/Mins to L Train /Laundry/Free Parking
Fridge, microwave, oven, stovetop
Beautiful, Remodeled Penthouse Unit in Old Town!
9.6 out of 10, Exceptional, (7)
"This property is huge for a city apartment. Our family of 5 (two parents, three kids) had plenty of space. The newly updated kitchen is very pretty. It is a short walk to many restaurants and Lincoln Park Zoo. The property manager was very responsive to my questions. We would definitely stay here again."
Beautiful, Remodeled Penthouse Unit in Old Town!
Living area
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (161)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
Outdoor dining
national historic home near downtown airports no parties no events
9.4 out of 10, Exceptional, (19)
"Had a great time used space for birthday event!!"
The price is HK$2,110
per night
15 May - 16 May
national historic home near downtown airports no parties no events
Terrace/patio
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (70)
"The house and location was perfect for our group trip to Chicago. Ample rooms and beds for everyone, and host was extremely responsive throughout the process and our stay. Walking distance to a bunch of great restaurants and bars. Would definitely stay again!"
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Property grounds
Ensuring a Very Pleasant & Memorable Stay! Close to 360 Chicago, Pet-Friendly
9.4 out of 10, Exceptional, (3)
"Easy check in, staff on property were so nice. Property has a lap pool and a gym. Location was great and price was very comfortable."
The price is HK$1,484
per night
27 May - 28 May
Ensuring a Very Pleasant & Memorable Stay! Close to 360 Chicago, Pet-Friendly
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (396)
"It was amazing to have a whole apartment for the price of a hotel room... less actually. Their system is simple and painless. I will book here again!"
The price is HK$977
per night
27 May - 28 May
Sentral Michigan Avenue
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (222)
"Kasa is good overall. However, the cleaning lady just barged in my room without knocking and pretended to be checking the place. Not good at all. No proper MANNER. There is only one person in the lobby checking in guests as well as taking luggages for storage. It would be helpful to have a separate person designated so guests are not waiting."
Kasa Magnificent Mile Chicago
Property grounds
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, (9)
"Excellent"
The price is HK$1,172
per night
19 May - 20 May
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Don't see what you're looking for?
See all available properties in Glencoe
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.

Other types of properties in Glencoe you may be interested in

View from property
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2869)
"We stayed here for two nights and it was amazing! We will come back again)"
The price is HK$1,329
per night
27 May - 28 May
River Hotel
Exterior
The Westin Michigan Avenue Chicago
4.5 star property
8.6 out of 10, Excellent, (1002)
"We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)"
The price is HK$1,633
per night
27 May - 28 May
The Westin Michigan Avenue Chicago
Front of property
Warwick Allerton - Chicago
4.0 star property
7.8 out of 10, Good, (2580)
"Great location near shops, food outlet’s, etc"
The price is HK$898
per night
27 May - 28 May
Warwick Allerton - Chicago
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

Are there holiday rentals in Glencoe?

Yes, there are holiday rentals close to the most popular sights in Glencoe, or you can select a more secluded option if you're looking for a relaxing stay. Glencoe is known for its shopping and restaurants. Make sure you have time to check out the forests while you're in the area.

What are some of the best holiday rentals that Glencoe has to offer?

Luxury Home Away From Your Home: This holiday home rental outside of Glencoe has air conditioning and cable TV to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

What’s there to see and do in Glencoe?

Lake Michigan and Chicago Botanic Garden are a couple of scenic spots to enjoy the outdoors, whereas Writers Theatre is one of the cultural attractions. You’ll find favourite places to visit such as Naval Base Great Lakes and Wrigley Field in the wider area.

What’s a holiday rental in Glencoe like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Glencoe. Holiday rentals offer extras like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for small groups.