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Winnetka Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Winnetka vacation rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,198 reviews)
"Great location"
United States
JAVIER
The price is AED 609
AED 822 total
includes taxes & fees
1 Jul - 2 Jul
Sentral Michigan Avenue
TV, offices

Downtown Chicago Stay with Free In & Out Parking 5

Downtown Chicago Stay with Free In & Out Parking 5
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"This VRBO was perfect for our family as we visited our college student in downtown Chicago. Plenty of space, sparkling clean, comfy beds. Only two things that I think could be improved/better communicated: only one key card is provided, and the beds are full size not queen (but they were SUPER comfortable!!!)"
United States
Gina C.
The price is AED 753
AED 1,908 total
includes taxes & fees
7 Jul - 8 Jul
Downtown Chicago Stay with Free In & Out Parking 5
Dining

LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is AED 613
AED 811 total
includes taxes & fees
28 Jun - 29 Jun
LIVN Millennium Park Downtown Chicago Studio
Pool

South Loop Rooftop With In and Out Parking 2

South Loop Rooftop With In and Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay! Parking was easy and secure. The building was super clean and had lots of amenities. Host was very responsive to messages and very accommodating to our last minute schedule changes. "
United States
Kara V.
The price is AED 1,168
AED 2,493 total
includes taxes & fees
21 Jul - 22 Jul
South Loop Rooftop With In and Out Parking 2
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.8 out of 10, Exceptional, (6 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is AED 973
AED 2,199 total
includes taxes & fees
28 Jun - 29 Jun
River North Rooftop With In and Out Parking 3
TV, offices

River North Rooftop With In and Out Parking 6

River North Rooftop With In and Out Parking 6
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"Host was amazing, very responsive. VRBO was spotless! Great location! Would definitely stay here again."
United States
Amy L.
The price is AED 775
AED 1,958 total
includes taxes & fees
19 Jul - 20 Jul
River North Rooftop With In and Out Parking 6
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (496 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is AED 888
AED 1,133 total
includes taxes & fees
30 Jun - 1 Jul
Level Chicago – Old Town
Fridge, microwave, oven, stovetop

Beautiful Unit CHI in Prime River North - 1

Beautiful Unit CHI in Prime River North - 1
Downtown Chicago
9.2 out of 10, Wonderful, (22 reviews)
"Location was fun"
United States
Robert L.
The price is AED 562
AED 1,564 total
includes taxes & fees
3 Jul - 4 Jul
Beautiful Unit CHI in Prime River North - 1
1 bedroom, iron/ironing board, travel crib, WiFi

LIVN West Loop Chicago Classic Queen Studio

LIVN West Loop Chicago Classic Queen Studio
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
The price is AED 573
AED 768 total
includes taxes & fees
1 Jul - 2 Jul
LIVN West Loop Chicago Classic Queen Studio
TV, offices

Modern West Loop Gem-City Views & Prime Location 2

Modern West Loop Gem-City Views & Prime Location 2
Downtown Chicago
9.4 out of 10, Exceptional, (9 reviews)
"Excellent location, very clean & comfortable. West Loop is an awesome area to stay in Chicago. Seamless check in process."
United States
Dean R.
The price is AED 1,455
AED 3,300 total
includes taxes & fees
28 Jun - 29 Jun
Modern West Loop Gem-City Views & Prime Location 2
Property grounds

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (13 reviews)
The price is AED 1,006
AED 2,312 total
includes taxes & fees
8 Jul - 9 Jul
ENVITAE Hotel, 4BR Luxury Modern Apartments
Interior

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
The price is AED 1,605
AED 3,159 total
includes taxes & fees
9 Jul - 10 Jul
Premium Urban 4BR - Perfect Mix of Comfort & Location
Lobby

Spacious House ~3min walk WrigleyField~Free Prkg

Spacious House ~3min walk WrigleyField~Free Prkg
Lakeview
9.4 out of 10, Exceptional, (34 reviews)
"Beautiful property! Great time enjoying a “treat yourself” weekend. Nice amenities and thoughtful touches. "
United States
Julie F.
The price is AED 2,182
AED 4,093 total
includes taxes & fees
28 Jun - 29 Jun
Spacious House ~3min walk WrigleyField~Free Prkg
Studio | Exterior

Ground Floor Studios in Chicago by 747 Lofts

Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
West Town
8.6 out of 10, Excellent, (23 reviews)
"Great area and surprisingly nice room!"
United States
Michael
The price is AED 377
AED 682 total
includes taxes & fees
8 Jul - 9 Jul
Ground Floor Studios in Chicago by 747 Lofts
Iron/ironing board, WiFi, bed sheets

Cabin 104 by 747 Lofts

Cabin 104 by 747 Lofts
West Town
10.0 out of 10, Exceptional, (9 reviews)
"The place was great"
United States
bonnie c.
Cabin 104 by 747 Lofts
Private kitchen

Wrigley Field MVP Suite 1 Bedroom Apartment

Wrigley Field MVP Suite 1 Bedroom Apartment
Lakeview
9.6 out of 10, Exceptional, (14 reviews)
"Great location. 30 steps to Wrigley field. Clean. Safe. Very clean apt."
United States
Curt M.
The price is AED 657
AED 2,448 total
includes taxes & fees
6 Jul - 7 Jul
Wrigley Field MVP Suite 1 Bedroom Apartment
TV

Wrigley Field All Star Suite 3 Bedrooms 2 Bath

Wrigley Field All Star Suite 3 Bedrooms 2 Bath
Lakeview
9.6 out of 10, Exceptional, (24 reviews)
"Enjoyed a dinner party with friends Place was perfect Management helpful "
United States
Vince K.
The price is AED 1,392
AED 3,472 total
includes taxes & fees
6 Jul - 7 Jul
Wrigley Field All Star Suite 3 Bedrooms 2 Bath
Fireplace

Wrigley Field Home Run 4 Bedroom, 2 Bathroom

Wrigley Field Home Run 4 Bedroom, 2 Bathroom
Lakeview
9.6 out of 10, Exceptional, (20 reviews)
"Would definitely stay there again "
United States
Enrique
The price is AED 1,759
AED 3,989 total
includes taxes & fees
8 Jul - 9 Jul
Wrigley Field Home Run 4 Bedroom, 2 Bathroom
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.0 out of 10, Wonderful, (38 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is AED 768
AED 901 total
includes taxes & fees
29 Jun - 30 Jun
Wrigleyville Suites
Terrace/patio

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (55 reviews)
"So hospitable "
United States
Adrian
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
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 Winnetka Hotel Reviews

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Did a turn and burn stay here (checked in Saturday and checked out Monday) and had a pleasant visit. The front desk customer service was A+. My only 2 feedback are: the valet attendant should be more attentive. I waited 10 mins while the valet attendant was chatting away with a co-worker and then started laughing with I assume a customer. I had to politely interrupt to get service. 2nd feedback: I was on the 23rd floor and soon as I stepped off the elevator, the hallway and room had a sour/mildew odor."
Latasha 2-night trip
Posted 3 hours ago
Hilton Chicago/Magnificent Mile Suites

Frequently asked questions

Can I find vacation rentals in Winnetka?

Yes, we offer vacation rentals in Winnetka near Chocolate Box, or you can go with a more remote option if you'd like a relaxing place to stay. 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 are some of the best vacation rentals in Winnetka?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: Visitors like this Winnetka vacation home rental. It is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Winnetka?

Lake Michigan and Maple Street Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Chocolate Box. While in the area, you can also visit popular places like Wrigley Field and Naval Base Great Lakes.

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.