Winnetka Vacation Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

This weekend
Next weekend

Vacation Rentals in Winnetka

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (739)
"Great family place to stay. "
The price is CA $198
CA $273 total
includes taxes & fees
May 26 - May 27
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (486)
"Great stay "
The price is CA $178
CA $208 total
includes taxes & fees
May 26 - May 27
Sonder South Wabash

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (277)
"Charming, minimalist, accessible and modern, just what I needed, ideal for couples or single people who want to enjoy the city."
The price is CA $176
CA $207 total
includes taxes & fees
May 26 - May 27
Sonder Market Hall

Sonder The Burnham Apartments

3.5 star property
9.0 out of 10, Wonderful, (164)
"Easy and great for extended stay."
The price is CA $195
CA $229 total
includes taxes & fees
May 26 - May 27
Sonder The Burnham Apartments

Sonder Onterie

3.5 star property
8.2 out of 10, Very good, (14)
"Nice quiet stay. The rooms are beautiful!"
The price is CA $206
CA $242 total
includes taxes & fees
May 26 - May 27
Sonder Onterie

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (308)
"It was really nice overall! Would recommend "
The price is CA $303
CA $387 total
includes taxes & fees
May 12 - May 13
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (396)
"Great stay "
Kasa Magnificent Mile Chicago

Sonder Jewelers Row

3.5 star property
8.4 out of 10, Very good, (151)
"This was the perfect stay for us this past weekend "
The price is CA $201
CA $236 total
includes taxes & fees
May 26 - May 27
Sonder Jewelers Row

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (280)
"Great place , Clean easy check-in and great location ."
Kasa South Loop Chicago

The Neighborhood Hotel-Little Italy

3.5 star property
9.8 out of 10, Exceptional, (154)
"Another amazing stay in Little Italy!"
The Neighborhood Hotel-Little Italy

Sonder The Plymouth

3.5 star property
8.4 out of 10, Very good, (97)
"The apartment was perfect. Location made everything walkable. Super clean. Bright rooms. Bed was super comfy. I can’t say enough good things about this place. I loved it and would stay here again on my next trip to Chicago "
The price is CA $165
CA $194 total
includes taxes & fees
May 26 - May 27
Sonder The Plymouth

Sonder The Opal

3.5 star property
8.6 out of 10, Excellent, (34)
"Great property. Really like the 3 bedroom set up with kitchen as it is perfect for travelling with children. "
The price is CA $172
CA $202 total
includes taxes & fees
May 11 - May 12
Sonder The Opal

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (138)
"i really enjoyed this cozy apartment, it had all the amenities and friendly staff to help me through the check-in process. "
The price is CA $227
CA $266 total
includes taxes & fees
May 4 - May 5
Kasa River North Chicago

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (47)
"I enjoyed my stay! Thanks!"
The price is CA $239
CA $281 total
includes taxes & fees
May 27 - May 28
Sonder Greektown

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (59)
"The breakfast was wonderful. Everyone was very nice and friendly."
The price is CA $193
CA $220 total
includes taxes & fees
May 21 - May 22
The Gem Museum Suites

Wrigleyville Suites

2.0 star property
8.8 out of 10, Excellent, (5)
The price is CA $170
CA $269 total
includes taxes & fees
May 2 - May 3
Wrigleyville Suites

HUGE! 3bdrm Private HOME-Garage-RoofDeck Skyline view-EVTesla-PETS OK-Sleeps12

10.0 out of 10, Exceptional, (4)
"Great property and very kind and responsive hosts. I would be happy to stay here again. "
HUGE! 3bdrm Private HOME-Garage-RoofDeck Skyline view-EVTesla-PETS OK-Sleeps12

Bright Garden Studio

9.0 out of 10, Wonderful, (21)
"Great spot to stay, very accommodating and everything we needed! Will be back for future visits."
The price is CA $116
CA $331 total
includes taxes & fees
May 19 - May 20
Bright Garden Studio

2-bedroom apartment just 2 minutes drive to Wrigley Field

2.0 star property
9.6 out of 10, Exceptional, (12)
"Great time and location. "
The price is CA $137
CA $355 total
includes taxes & fees
May 6 - May 7
2-bedroom apartment just 2 minutes drive to Wrigley Field

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (117)
"Perfect for what we were looking for!"
Luxury Home Away From Your Home
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.
Don't see what you're looking for?
See all available properties in Winnetka
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Winnetka you may be interested in

Embassy Suites by Hilton Chicago Downtown River North

4.0 star property
8.4 out of 10, Very good, (3967)
"Great location, nice buffet breakfast and good stuffs."
The price is CA $245
CA $288 total
includes taxes & fees
May 11 - May 12
Embassy Suites by Hilton Chicago Downtown River North

Congress Plaza Hotel

3.5 star property
8.0 out of 10, Very good, (8726)
"Great stay"
The price is CA $165
CA $193 total
includes taxes & fees
May 27 - May 28
Congress Plaza Hotel

Hilton Chicago/Magnificent Mile Suites

3.5 star property
8.8 out of 10, Excellent, (2168)
"Nice place to stay "
The price is CA $222
CA $261 total
includes taxes & fees
May 8 - May 9
Hilton Chicago/Magnificent Mile Suites
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

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?

Luxury Home Away From Your Home: You might want to consider this vacation home rental near Winnetka, which is equipped with a barbecue grill, air-conditioning, and a Smart TV to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Winnetka?

Choose from 3 Expedia vacation rentals in Winnetka for a memorable vacation.

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.