The Best Vacation Rentals - Vacation Rentals in Chocolate Box

Dates

Price

Guests

More

When do you want to travel?

We search multiple sites to find you the best prices.

Compare Price with Other Partners

New

From US $1,038

         

New

Villa

Chicago North Shore Luxury Home Vacation Rental Located in Upscale Neighborhood

• Air Conditioner
• Parking
• TV

• Chicago
• Wilmette

View Availability

From US $189

         

|

9.0 (120 Reviews)

Hotel

Residence Inn by Marriott Chicago Wilmette/Skokie

• Air Conditioner
• Parking
• Pet Friendly

• Chicago
• Wilmette

View Availability

From US $192

         

|

9.2 (678 Reviews)

Hotel

Residence Inn by Marriott Chicago Wilmette/Skokie

• Air Conditioner
• Parking
• Pool

• Chicago
• Wilmette

View Availability

From US $205

         

New

House

NEW! Bright Modern 3Bed 2.5Bath Evanston Home w/Parking

• Air Conditioner
• TV
• Security/Safety

• Chicago
• Evanston

View Availability

From US $140

         

New

Apartment

Charming 2-bedroom lower apartment with WiFi, AC in welcoming Wilmette

• Air Conditioner
• Pet Friendly
• Security/Safety

• Chicago
• Wilmette

View Availability

From US $396

         

10.0 (15 Reviews)

House

Warm and Cheerful 3 Bedroom Winnetka Townhouse

• Air Conditioner
• Parking
• TV

• Chicago
• Winnetka

View Availability

From US $230

         

10.0 (1 Review)

House

Charming, light-filled 5br Wilmette home

• Air Conditioner
• Parking
• Pet Friendly

• Chicago
• Wilmette

View Availability

From US $483

         

9.8 (10 Reviews)

House

Cozy 4 Bedroom/2 Bath Cozy Home In East Glenview With Inground Pool!

• Air Conditioner
• Parking
• Pet Friendly

• Chicago
• Glenview

View Availability

From US $556

         

New

House

Northbrook FHS Rental

• Air Conditioner
• Parking
• Pet Friendly

• Chicago
• Northbrook

View Availability

From US $536

         

New

House

Extended Stay Northbrook FHS Rental

• Air Conditioner
• Parking
• Pet Friendly

• Chicago
• Northbrook

View Availability

From US $1,240

         

10.0 (7 Reviews)

House

Chicago - NorthShore Private Vacation Rental Luxury 3 Story Victorian Mansion

• Air Conditioner
• Parking
• Pet Friendly

• Chicago
• Wilmette

View Availability

From US $267

         

10.0 (3 Reviews)

House

Updated Spacious Home -Near NWU- Hospitals+More

• Air Conditioner
• Parking
• Pet Friendly

• Chicago
• Wilmette

View Availability

From US $800

         

10.0 (2 Reviews)

House

North Shore 4 bedroom home near New Trier Schools

• Air Conditioner
• Pool
• View

• Chicago
• Winnetka

View Availability

New

From US $894

         

New

Villa

Chicago-Northshore Vacation Rental Luxury 5BR n5 Ba Victorian Mansion 7min Beach

• Air Conditioner
• Pet Friendly
• TV

• Chicago
• Wilmette

View Availability

From US $341

         

New

House

Charming 2-bedroom home in fantastic Winnetka, IL location

• Air Conditioner
• Security/Safety
• Bedding/Linens

• Chicago
• Winnetka

View Availability

From US $206

         

New

House

Charming 3-bedroom house with AC and WiFi in Wilmette

• Air Conditioner
• Pet Friendly
• Security/Safety

• Chicago
• Wilmette

View Availability

From US $157

         

10.0 (1 Review)

House

Spacious Townhouse in Wilmette near lake and NW

• Air Conditioner
• Parking
• Pet Friendly

• Chicago
• Wilmette

View Availability

From US $426

         

8.8 (3 Reviews)

Apartment

Chicago North Shore Close to NWU + Downtown + Beach + Restaurants + Train

• Air Conditioner
• Pet Friendly
• TV

• Chicago
• Wilmette

View Availability

From US $199

         

2.0 (1 Review)

Apartment

Resort-style, 1-bedroom apt in Wilmette

• Air Conditioner
• Pet Friendly
• Wheelchair Accessible

• Chicago
• Wilmette

View Availability

From US $580

         

New

House

Northbrook Rental

• Air Conditioner
• Parking
• Pet Friendly

• Illinois
• Chicago

View Availability

From US $504

         

New

House

Northbrook Rental

• Air Conditioner
• Parking
• Pet Friendly

• Chicago
• Northbrook

View Availability

From US $325

         

New

House

Great Hideaway in plain sight

• Air Conditioner
• Parking
• TV

• Chicago
• Evanston

View Availability

From US $300

         

New

House

Close to Northwestern U + Chicago + Beach + Restaurants + Train

• Air Conditioner
• Pet Friendly
• Security/Safety

• Chicago
• Wilmette

View Availability

From US $200

         

New

House

Cozy ranch house in wilmette

• Air Conditioner
• Pet Friendly
• Laundry

• Chicago
• Wilmette

View Availability

★ Pro Tip: Thebestvacationrentals makes it easy to compare the best listings on Thebestvacationrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Thebestvacationrentals homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chocolate Box.