Chocolate Box Villa Rentals

Compare Villas, Resorts, & Rentals in Chocolate Box, Winnetka, Illinois, USA

New Totally remodeled 4-bedroom house in Evanston
New
4 Bedrooms 2 Guests
From GB £540 per night
10.0 (6 Reviews)
4 Bedrooms 8 Guests
10.0 (57 Reviews)
2 Bedrooms 5 Guests
|
10.0 (3 Reviews)
3 Bedrooms 8 Guests
New
2 Bedrooms 6 Guests
10.0 (50 Reviews)
2 Bedrooms 6 Guests
From GB £172 per night
|
9.4 (86 Reviews)
1 Bedroom 2 Guests
10.0 (39 Reviews)
2 Bedrooms 4 Guests
|
10.0 (1 Review)
3 Bedrooms 8 Guests
10.0 (33 Reviews)
1 Bedroom 4 Guests
|
10.0 (1 Review)
2 Bedrooms 6 Guests
|
9.6 (7 Reviews)
2 Bedrooms 6 Guests
10.0 (32 Reviews)
2 Bedrooms 6 Guests
From GB £151 per night
|
8.8 (7 Reviews)
2 Bedrooms 5 Guests
10.0 (29 Reviews)
2 Bedrooms 5 Guests
|
8.0 (1 Review)
3 Bedrooms 11 Guests
From GB £110 per night
|
7.5 (2 Reviews)
1 Bedroom 8 Guests
10.0 (25 Reviews)
2 Bedrooms 5 Guests
|
7.0 (2 Reviews)
1 Bedroom 2 Guests
10.0 (19 Reviews)
2 Bedrooms 5 Guests
From GB £207 per night
|
6.3 (3 Reviews)
1 Bedroom 2 Guests
10.0 (15 Reviews)
2 Bedrooms 5 Guests
From GB £143 per night
|
5.0 (1 Review)
1 Bedroom 4 Guests
10.0 (15 Reviews)
1 Bedroom 4 Guests
|
4.0 (2 Reviews)
2 Bedrooms 4 Guests
From GB £345 per night
|
3.0 (1 Review)
2 Bedrooms 4 Guests
|
New
3 Bedrooms 11 Guests
10.0 (11 Reviews)
2 Bedrooms 4 Guests
|
New
1 Bedroom 2 Guests
From GB £212 per night
10.0 (11 Reviews)
2 Bedrooms 6 Guests
|
New
2 Bedrooms 6 Guests
|
New
1 Bedroom 8 Guests
10.0 (5 Reviews)
1 Bedroom 4 Guests
From GB £192 per night
10.0 (3 Reviews)
2 Bedrooms 5 Guests
10.0 (2 Reviews)
1 Bedroom 4 Guests
10.0 (2 Reviews)
1 Bedroom 2 Guests
From GB £183 per night
10.0 (2 Reviews)
1 Bedroom 2 Guests
From GB £202 per night
New
1 Bedroom 2 Guests
|
New
1 Bedroom 8 Guests
|
9.2 (1008 Reviews)
1 Bedroom 2 Guests
From GB £173 per night
|
New
1 Bedroom 2 Guests
|
9.2 (666 Reviews)
1 Bedroom 2 Guests
New
1 Bedroom 4 Guests
From GB £186 per night
|
9.0 (1003 Reviews)
1 Bedroom 2 Guests
From GB £690 per night
|
9.0 (86 Reviews)
20 Bedrooms 14 Guests
From GB £174 per night
New
1 Bedroom 2 Guests
|
8.9 (113 Reviews)
125 Bedrooms 8 Guests
|
8.8 (711 Reviews)
216 Bedrooms 46 Guests
New
1 Bedroom 2 Guests
From GB £172 per night
|
8.5 (651 Reviews)
10 Bedrooms 24 Guests
From GB £159 per night
New
1 Bedroom 2 Guests
From GB £136 per night
|
8.5 (281 Reviews)
145 Bedrooms 44 Guests
From GB £159 per night
New
1 Bedroom 2 Guests
From GB £201 per night
|
8.4 (183 Reviews)
114 Bedrooms 59 Guests
From GB £153 per night
New
1 Bedroom 2 Guests
|
8.3 (153 Reviews)
149 Bedrooms 15 Guests
From GB £172 per night
|
8.3 (35 Reviews)
97 Bedrooms 57 Guests
|
7.9 (478 Reviews)
369 Bedrooms 21 Guests

About Chocolate Box Vacation Rentals

There are more than 304 incredible getaway rentals that are available in Chocolate Box. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Chocolate Box.

BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Chocolate Box, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Chocolate Box. Places to stay near Chocolate Box are 599.55 ft² on average, with prices averaging GB £229 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Chocolate Box. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.

Frequently Asked Questions About Chocolate Box?

What are the top hotels or resorts in Chocolate Box?

How many hotels, resorts, or rentals are available in Chocolate Box?

BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2025 is over 304 in the Chocolate Box area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Chocolate Box. 

Nearby Neighborhood (12)

Neighborhood Property Count
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Edgewater Rental Villas and Private Getaways in Chicago, Illinois 55
Wrigleyville Rental Villas and Private Getaways in Chicago, Illinois 45
Uptown Rental Villas and Private Getaways in Chicago, Illinois 34
Ravenswood Rental Villas and Private Getaways in Chicago, Illinois 29
Bucktown Rental Villas and Private Getaways in Chicago, Illinois 24
Boystown Rental Villas and Private Getaways in Chicago, Illinois 679
Andersonville Rental Villas and Private Getaways in Chicago, Illinois 978