Search Vacation Homes in Winnetka

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Check prices for these dates

In two weeks
Oct 17 - Oct 19
In one month
Oct 31 - Nov 2
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28

Vacation Homes in Winnetka

Belmont House, Classy & Chic/walk to Wrigley Field
Interior

Belmont House, Classy & Chic/walk to Wrigley Field

9.4 out of 10, Exceptional, (53)
"Booked this place as we had a concert at Wrigley Field. The owner was phenomenal. 100% advertised. Great place to stay. 10 out of 10 would book again if in the area."
Belmont House, Classy & Chic/walk to Wrigley Field
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
Property grounds

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

9.2 out of 10, Wonderful, (55)
"The building is from the 19th century which made it a really unique experience. The hosts were amazing and quick to respond. We went to check out the Linkin Park concert in the United Center and it was a 5min walk from the property. "
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
LUXE 3 BR, 2 BA + Hot Tub
Private kitchen

LUXE 3 BR, 2 BA + Hot Tub

8.8 out of 10, Excellent, (33)
"The house had a lot of gnats and we were bit up"
$311 nightly
The price is $333
Oct 15 - Oct 16
Total with taxes and fees
LUXE 3 BR, 2 BA + Hot Tub
Theater • Game Room • Gym • Firepit • 4BR Home
Dining

Theater • Game Room • Gym • Firepit • 4BR Home

7.6 out of 10, Good, (10)
"Comfy beds and a great house for kids and adults."
$421 nightly
The price is $512
Oct 28 - Oct 29
Total with taxes and fees
Theater • Game Room • Gym • Firepit • 4BR Home
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Fridge, microwave, oven, stovetop

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Cozy 3-bedroom house in family-oriented Melrose Park.
Property grounds

Cozy 3-bedroom house in family-oriented Melrose Park.

10.0 out of 10, Exceptional, (23)
"Excellent place to stay and host provided great communication. The house is very nice and we also enjoyed the fire pit and hot tub, too! We highly recommend staying at this house and we will be back soon!"
Cozy 3-bedroom house in family-oriented Melrose Park.
Breathtaking home close to Schaumburg, Chicago
Dining

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (74)
"very nice four bedroom home and a great location."
Breathtaking home close to Schaumburg, Chicago
Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG
Fridge, microwave, oven, stovetop

Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG

2.0 star property
9.8 out of 10, Exceptional, (13)
"We loved Retro House, a real treasure inside Chicago. Comfortable, quiet and safe."
Oak Park IL · Charming Retro 2BR Cottage/Train/Laundry/FREE PKG
2BR Traveler`s Favorite • Modern and Clean
Fridge, microwave, oven, stovetop

2BR Traveler`s Favorite • Modern and Clean

10.0 out of 10, Exceptional, (2)
"Clean, comfortable, and secure"
$304 nightly
The price is $376
Oct 7 - Oct 8
Total with taxes and fees
2BR Traveler`s Favorite • Modern and Clean
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Terrace/patio

Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown

2.0 star property
9.0 out of 10, Wonderful, (9)
"Great"
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Wrigley Field/Lakeview -Entire Home- Large Groups!
Fridge, microwave, oven, stovetop

Wrigley Field/Lakeview -Entire Home- Large Groups!

10.0 out of 10, Exceptional, (84)
"We had a fantastic experience staying here. The layout was spacious and worked perfectly for our group of 10 adults—plenty of room for everyone to relax and spread out. The home was clean, well-kept, and exactly as described. Check-in and check-out were a breeze, and the neighborhood was quiet and welcoming with easy access to public transportation, which made getting around simple. Overall, a 10/10 stay—we really enjoyed our time and would definitely book again!"
Wrigley Field/Lakeview -Entire Home- Large Groups!
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Beach nearby

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

9.8 out of 10, Exceptional, (177)
"The house was spacious and perfect for our large group. "
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Master qtr close to nature & easy urban facilities
Exterior detail

Master qtr close to nature & easy urban facilities

9.8 out of 10, Exceptional, (67)
"Beautiful, quiet space."
$185 nightly
The price is $196
Nov 2 - Nov 3
Total with taxes and fees
Master qtr close to nature & easy urban facilities
Entire 3 Bedroom Cozy Unit
Smart TV, books

Entire 3 Bedroom Cozy Unit

9.4 out of 10, Exceptional, (23)
"This property was comfortable and convenient for our attendance at the Navy boot camp graduation. "
Entire 3 Bedroom Cozy Unit
Your Next Vacation Home
Private kitchen

Your Next Vacation Home

9.6 out of 10, Exceptional, (54)
"We enjoyed our stay"
$316 nightly
The price is $338
Oct 28 - Oct 29
Total with taxes and fees
Your Next Vacation Home
North Chi retreat – Navy, Sauna, Tiki Bar, Games
Fridge, microwave, oven, stovetop

North Chi retreat – Navy, Sauna, Tiki Bar, Games

9.8 out of 10, Exceptional, (8)
$462 nightly
The price is $473
Oct 6 - Oct 7
Total with taxes and fees
North Chi retreat – Navy, Sauna, Tiki Bar, Games
Inspiring Stone Grotto Sleeps 10-20 & Free Parking
Exterior

Inspiring Stone Grotto Sleeps 10-20 & Free Parking

9.8 out of 10, Exceptional, (28)
"Great location that was walking distance to everything we needed. There was more than enough room for our group and it was a comfortable stay."
Inspiring Stone Grotto Sleeps 10-20 & Free Parking
Enjoy Chicago/suburbs 2BR townhouse fully equipped
Fridge, microwave, oven, stovetop

Enjoy Chicago/suburbs 2BR townhouse fully equipped

10.0 out of 10, Exceptional, (12)
"I would recommend to anyone. "
Enjoy Chicago/suburbs 2BR townhouse fully equipped
Luxury Home - Pool Table/Bar/Patio
Interior

Luxury Home - Pool Table/Bar/Patio

10.0 out of 10, Exceptional, (4)
"Perfect for what we needed!"
$816 nightly
The price is $873
Oct 3 - Oct 4
Total with taxes and fees
Luxury Home - Pool Table/Bar/Patio
Home Sweet Home Spacious 4bed house with WiFi & Parking in fantastic Skokie
Fridge, microwave, oven, stovetop

Home Sweet Home Spacious 4bed house with WiFi & Parking in fantastic Skokie

8.0 out of 10, Very Good, (4)
"The house was in a nice neighborhood and was very roomy and comfortable. Will be back."
Home Sweet Home Spacious 4bed house with WiFi & Parking in fantastic Skokie
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

Freehand Chicago

Freehand Chicago

10/10 Excellent
"(Private queen room) the room was small but very comfortable. Everyone was very nice and friendly. Would absolutely stay again. "
jonathan 1-night trip
Posted 4 hours ago
Freehand Chicago

Find out more about Winnetka

Find out more about Winnetka

Winnetka Vacation Homes information

Number of reviews
657
Accommodation
583 Vacation Homes
Lowest Price
$196
Highest Price
$873

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