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Our top choices for Winnetka vacation rentals
1. The Gem Museum Suites
The Gem Museum Suites3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (301 reviews)
9.4/10
Exceptional
(301 reviews)
"Good breakfast"
"Good breakfast"
Zhaohua
The price is NT$6,566
NT$6,566
NT$7,517 total
includes taxes & fees
Nov 9 - Nov 10
2. Wrigleyville Suites
Wrigleyville Suites2.0 star property
Lakeview
9.4 out of 10, Exceptional, (49 reviews)
9.4/10
Exceptional
(49 reviews)
"Clean room"
"Clean room"Michael
The price is NT$4,876
NT$4,876
NT$5,723 total
includes taxes & fees
Nov 9 - Nov 10
3. Level Chicago – Old Town
Level Chicago – Old Town4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (558 reviews)
9.2/10
Wonderful
(558 reviews)
"Super clean and friendly staff! Would definitely stay here again"
"Super clean and friendly staff! Would definitely stay here again"Robert Edward
The price is NT$5,644
NT$5,644
NT$7,435 total
includes taxes & fees
Nov 23 - Nov 24
4. Sentral Michigan Avenue
Sentral Michigan Avenue4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,404 reviews)
9.0/10
Wonderful
(1,404 reviews)
"10/10 2nd time staying here!"
"10/10 2nd time staying here!"Rosa
The price is NT$4,176
NT$4,176
NT$4,902 total
includes taxes & fees
Dec 7 - Dec 8
5. Kasa Lake Shore Chicago
Kasa Lake Shore Chicago4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (83 reviews)
8.8/10
Excellent
(83 reviews)
"The bathroom was really clean. The beds were really comfortable"
"The bathroom was really clean. The beds were really comfortable"Jair
The price is NT$5,006
NT$5,006
NT$7,910 total
includes taxes & fees
Nov 22 - Nov 23
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.
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.
Find vacation rentals that suit your style
Top Winnetka Hotel Reviews
Holiday Inn Chicago O'Hare – Rosemont by IHG
Holiday Inn Chicago O'Hare – Rosemont by IHGRosemont
10/10 Excellent
I actually like the proximity to the airport. The hotel was clean, had good amenities and has a heated pool.
I actually like the proximity to the airport. The hotel was clean, had good amenities and has a heated pool.
Eero
L7 Chicago by LOTTE
L7 Chicago by LOTTEDowntown Chicago
10/10 Excellent
I stayed here to visit my child that attends the Art Institute and I was completely impressed. I will definitely stay here again.
I stayed here to visit my child that attends the Art Institute and I was completely impressed. I will definitely stay here again.
Erin
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by HiltonDowntown Chicago
10/10 Excellent
Great location
Great location
blerina
Hyatt Regency Chicago
Hyatt Regency ChicagoDowntown Chicago
10/10 Excellent
Wonderful stay in a great location!
Wonderful stay in a great location!
Brooke
Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoDowntown Chicago
10/10 Excellent
We chose this hotel last minute and we were nervous because there were a couple recent negative reviews. There were 4 of us in our family and couldn't find anything negative to say about the hotel. The only disappointing fact was that the rooftop bar was not open but that wasn't a big deal. Everything was very clean. I actually wiped the floor in our room with a wet, white wash cloth, it was clean! There was no hair in the bathroom from a previous guest. There was no hair in the bed from a...
We chose this hotel last minute and we were nervous because there were a couple recent negative reviews. There were 4 of us in our family and couldn't find anything negative to say about the hotel. The only disappointing fact was that the rooftop bar was not open but that wasn't a big deal. Everything was very clean. I actually wiped the floor in our room with a wet, white wash cloth, it was clean! There was no hair in the bathroom from a previous guest. There was no hair in the bed from a...
Donna
Hyatt Place Chicago/River North
Hyatt Place Chicago/River NorthDowntown Chicago
10/10 Excellent
Good
Good
Saad
citizenM Chicago Downtown
citizenM Chicago DowntownDowntown Chicago
10/10 Excellent
Great location, clean room and friendly staff!
Great location, clean room and friendly staff!
Diani
The Royal Sonesta Chicago Downtown
The Royal Sonesta Chicago DowntownDowntown Chicago
10/10 Excellent
Excellent Customer Service
Excellent Customer Service
Grace
Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake ChicagoDowntown Chicago
10/10 Excellent
This was the fourth time I’ve stayed here, and I’ll keep coming back. The location is very handy for families of Columbia College, the rooms are clean, comfortable and well appointed. The staff is extremely friendly and helpful, and it’s priced well.
This was the fourth time I’ve stayed here, and I’ll keep coming back. The location is very handy for families of Columbia College, the rooms are clean, comfortable and well appointed. The staff is extremely friendly and helpful, and it’s priced well.
Jennifer
Swissotel - Chicago
Swissotel - ChicagoDowntown Chicago
10/10 Excellent
It was okay but, I wish they specified the clearance level for the self parking if we would of have know ahead of time we would of brought our smaller car
It was okay but, I wish they specified the clearance level for the self parking if we would of have know ahead of time we would of brought our smaller car
Brian
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHGDowntown Chicago
10/10 Excellent
The customer service was great. And the pool is so pretty!
The customer service was great. And the pool is so pretty!
Rosemary
Courtyard by Marriott Chicago Magnificent Mile
Courtyard by Marriott Chicago Magnificent MileDowntown Chicago
10/10 Excellent
Forever one of my favorite hotels and one of my two favorite Courtyard properties I've ever stayed at! This is the 3rd year in a row we've stayed here when coming to Chicago and it never disappoints. It feels like a high-end hotel for an affordable price (considering where it is)! The staff is great super helpful, rooms are so clean and overall just is one of the nicest places! Highly recommend if you're looking for a spot in Chicago!
Forever one of my favorite hotels and one of my two favorite Courtyard properties I've ever stayed at! This is the 3rd year in a row we've stayed here when coming to Chicago and it never disappoints. It feels like a high-end hotel for an affordable price (considering where it is)! The staff is great super helpful, rooms are so clean and overall just is one of the nicest places! Highly recommend if you're looking for a spot in Chicago!
adriana
Springhill Suites by Marriott Chicago Downtown/ River North
Springhill Suites by Marriott Chicago Downtown/ River NorthDowntown Chicago
10/10 Excellent
Recently stayed at the Springhill Suites/River North. Could not have picked a better location for the first time in Chicago. Tons of local dining options. Close to landmarks. Easily walked to the Magnificient Mile(Michigan Ave) Walked to the subway to go to Wrigley Field and the United Center. Hotel was excellent. Clean, the staff was excellent in all areas. Free breakfast was fresh and good. Highly recommend overall.
Recently stayed at the Springhill Suites/River North. Could not have picked a better location for the first time in Chicago. Tons of local dining options. Close to landmarks. Easily walked to the Magnificient Mile(Michigan Ave) Walked to the subway to go to Wrigley Field and the United Center. Hotel was excellent. Clean, the staff was excellent in all areas. Free breakfast was fresh and good. Highly recommend overall.
Michael
Fairfield Inn & Suites Chicago Downtown/River North
Fairfield Inn & Suites Chicago Downtown/River NorthDowntown Chicago
10/10 Excellent
This hotel met our expectations. All the city attractions were within a walkable distance. The staff at breakfast was amazing! Shout out to Javier who was so welcoming and friendly :)
This hotel met our expectations. All the city attractions were within a walkable distance. The staff at breakfast was amazing! Shout out to Javier who was so welcoming and friendly :)
Claribeth
Hampton Inn & Suites Chicago Downtown
Hampton Inn & Suites Chicago DowntownDowntown Chicago
10/10 Excellent
I enjoyed my stay here. I didn’t get a chance to experience breakfast or the pool, but it's nice that they're avaliable. I loved the area, very easy to walk for food and entertainment. The bed does need replacing as it makes a squeaking noise when you sit on it and the mattress wasn't that comfortable. Even with that, I would stay here again.
I enjoyed my stay here. I didn’t get a chance to experience breakfast or the pool, but it's nice that they're avaliable. I loved the area, very easy to walk for food and entertainment. The bed does need replacing as it makes a squeaking noise when you sit on it and the mattress wasn't that comfortable. Even with that, I would stay here again.
Shatani
Arlo Chicago
Arlo ChicagoDowntown Chicago
10/10 Excellent
Arlo Chicago is in the perfect location for walkable access to so many Chicago sights, excellent food (please try the Broken English Taco Pub around the corner!), bars, shopping, etc. It was also very conveniently located to access the L when we needed to get to other parts of the city!
The staff was BEYOND accommodating, friendly, and helpful. The room was clean and exceeded all comfort expectations!
I also highly recommend the lobby bar for a great happy hour spot!!!
Everyone at this hotel...
Arlo Chicago is in the perfect location for walkable access to so many Chicago sights, excellent food (please try the Broken English Taco Pub around the corner!), bars, shopping, etc. It was also very conveniently located to access the L when we needed to get to other parts of the city!
The staff was BEYOND accommodating, friendly, and helpful. The room was clean and exceeded all comfort expectations!
I also highly recommend the lobby bar for a great happy hour spot!!!
Everyone at this hotel...
Lina
Heart O' Chicago
Heart O' ChicagoEdgewater
10/10 Excellent
The motel was easy to get to and the room itself was very clean and well presented. I appreciate the breakfast too.
The motel was easy to get to and the room itself was very clean and well presented. I appreciate the breakfast too.
Anonymous traveler
Hotel 505 River North
Hotel 505 River NorthDowntown Chicago
10/10 Excellent
Across from Nordstroms! Staff helpfu!
Across from Nordstroms! Staff helpfu!
shanea
Residence Inn by Marriott Chicago Downtown / River North
Residence Inn by Marriott Chicago Downtown / River NorthDowntown Chicago
10/10 Excellent
Big spacious room with complete kitchen. Beautiful views of the city. Restaurants and CVS pharmacy nearby. Decent selection of foods on breakfast buffet. Walking distance to the Navy Pier, Riverwalk and the Millennium Park. Parking garage is great but it is $55/ day extra.
Big spacious room with complete kitchen. Beautiful views of the city. Restaurants and CVS pharmacy nearby. Decent selection of foods on breakfast buffet. Walking distance to the Navy Pier, Riverwalk and the Millennium Park. Parking garage is great but it is $55/ day extra.
Arlene
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile SuitesDowntown Chicago
10/10 Excellent
I was traveling with two 14 year olds on a business/vacation trip and we stayed here for five days. The location is great. I wanted a hotel that was convenient to the major attractions and downtown, and safe for the boys to walk around on their own. We were able to walk to Navy Pier, Millennium Park, the Loop, and the Hancock Building. It's a good 20-25 minute walk to Navy Pier, but you walk along Lakeshore Drive and it's very enjoyable.
The property is very nice, although we didn't get the two...
I was traveling with two 14 year olds on a business/vacation trip and we stayed here for five days. The location is great. I wanted a hotel that was convenient to the major attractions and downtown, and safe for the boys to walk around on their own. We were able to walk to Navy Pier, Millennium Park, the Loop, and the Hancock Building. It's a good 20-25 minute walk to Navy Pier, but you walk along Lakeshore Drive and it's very enjoyable.
The property is very nice, although we didn't get the two...
Joanna
Find out more about Winnetka
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Frequently Asked Questions
Can I find vacation rentals in Winnetka?
Yes, we offer vacation rentals near the most popular attractions in Winnetka, or you can go with a more remote option if you're looking for relaxation. Winnetka is known for its shopping and forests. Make sure you have time to check out the sporting events and restaurants during your trip.
What can I see and do in Winnetka?
Lake Michigan and Maple Street Beach are a couple of lovely local spots to get outside and enjoy nature. While in the area, you can also visit popular places like Wrigley Field and Navy Pier.
What are vacation rentals like in Winnetka?
Vacation rentals are private accommodations you can stay in for a couple days or more in Winnetka. Vacation rentals feature extras such as hot tubs, fire pits, and patios so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for family trips.