Cook County Holiday Rentals
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.41 mi to center
10.0Exceptional
(417 Reviews)
1 Bedroom
1 Bath
4 Guests
Oceanfront
Parking
Pool
Ocean View
US $253/Night
7 Nights - US $1,769
Apartment
- Chicago
- ·
- Lake View East
- 0.30 mi to center
10.0Exceptional
(14 Reviews)
1 Bedroom
1 Bath
2 Guests
699.65 ft²
Internet
Child Friendly
US $256/Night
7 Nights - US $1,792
Bed & Breakfast
10.0Exceptional
(548 Reviews)
1 Bedroom
1 Bath
- Parking
Balcony/Terrace
Air Conditioner- Internet
US $190/Night
7 Nights - US $1,331
Apartment
- Chicago
- ·
- Des Plaines
- 1.10 mi to center
10.0Exceptional
(288 Reviews)
1 Bedroom
1 Bath
2 Guests
151 ft²
Kitchen- Air Conditioner
- Child Friendly
TV
US $98/Night
7 Nights - US $687
Apartment
10.0Exceptional
(12 Reviews)
1 Bedroom
1 Bath
4 Guests
452.08 ft²
Private Pool- Oceanfront
Breakfast- Parking
US $117/Night
7 Nights - US $819
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.41 mi to center
10.0Exceptional
(233 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $253/Night
7 Nights - US $1,769
Condo
- Chicago
- ·
- Ukrainian Village
- 0.23 mi to center
10.0Exceptional
(228 Reviews)
2 Bedrooms
2 Baths
9 Guests
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $458/Night
7 Nights - US $3,209
Condo
- Chicago
- ·
- Ukrainian Village
- 0.13 mi to center
10.0Exceptional
(213 Reviews)
1 Bedroom
1 Bath
5 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $296/Night
7 Nights - US $2,073
Apartment
10.0Exceptional
(211 Reviews)
1 Bedroom
1 Bath
2 Guests
151 ft²
- Kitchen
- Air Conditioner
Pet Friendly- Child Friendly
US $56/Night
7 Nights - US $390
Luxury Holiday Rentals in Cook County
Over 10000+ Luxury Holiday Rentals in or Near Cook County
House
- Chicago
- ·
- Barrington
- 1.90 mi to center
4 Bedrooms
2 Baths
7 Guests
- Air Conditioner
- Internet
Laundry
Security/Safety
Unlock the Best Price
New
Apartment
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
10 Guests
1076.39 ft²
- Parking
- Pool
- Air Conditioner
- Internet
US $10,000/Night
7 Nights - US $70,000
House
- Chicago
- ·
- Schaumburg
- 1.38 mi to center
1 Bedroom
1 Bath
4 Guests
1797.57 ft²
- Parking
- Pool
- Balcony/Terrace
- Child Friendly
US $8,000/Night
7 Nights - US $56,000
RV Rental
- Chicago
- ·
- Barrington
- 2.01 mi to center
1 Bedroom
1 Bath
9 Guests
- Child Friendly
- Security/Safety
US $6,160/Night
7 Nights - US $43,119
Apartment
- Chicago
- ·
- Near South Side
- 0.34 mi to center
5 Bedrooms
3 Baths
12 Guests
1496.18 ft²
EV Charge Station- Parking
- Balcony/Terrace
- Air Conditioner
US $4,545/Night
7 Nights - US $31,814
Apartment
10.0Exceptional
(11 Reviews)
5 Bedrooms
2 Baths
6 Guests
1800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $4,519/Night
7 Nights - US $31,634
Bed & Breakfast
- Chicago
- ·
- East Village
- 0.24 mi to center
8 Bedrooms
8 Baths
16 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $4,197/Night
7 Nights - US $29,376
Hotel
- Chicago
- ·
- Rush and Division
- 0.09 mi to center
3 Baths
1515 ft²
- Parking
- Pool
Spa- Balcony/Terrace
US $4,047/Night
7 Nights - US $28,331
House
4 Bedrooms
2 Baths
10 Guests
2497.23 ft²
- Parking
- Internet
- Child Friendly
- Security/Safety
US $3,786/Night
7 Nights - US $26,500
Top-Rated Holiday Rentals with a Pool in Cook County
Over 1564+ The Best Private Villas and Holiday Rentals in Cook County with a Pool
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.42 mi to center
10.0Exceptional
(68 Reviews)
1 Bedroom
1 Bath
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $224/Night
7 Nights - US $1,571
House
10.0Exceptional
(46 Reviews)
3 Bedrooms
2 Baths
7 Guests
1200 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $668/Night
7 Nights - US $4,677
Apartment
10.0Exceptional
(44 Reviews)
3 Bedrooms
2 Baths
7 Guests
1400 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $474/Night
7 Nights - US $3,316
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.42 mi to center
10.0Exceptional
(43 Reviews)
1 Bedroom
1 Bath
2 Guests
735 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $191/Night
7 Nights - US $1,337
Condo
10.0Exceptional
(36 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $421/Night
7 Nights - US $2,948
Apartment
10.0Exceptional
(33 Reviews)
2 Bedrooms
2 Baths
5 Guests
1250 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $439/Night
7 Nights - US $3,074
Apartment
10.0Exceptional
(22 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $451/Night
7 Nights - US $3,154
Apartment
10.0Exceptional
(21 Reviews)
2 Bedrooms
2 Baths
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $437/Night
7 Nights - US $3,057
Apartment
10.0Exceptional
(17 Reviews)
1 Bedroom
1 Bath
4 Guests
750 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $416/Night
7 Nights - US $2,910
Pet-Friendly Holiday Rentals in Cook County
Over 4046+ Pet-Friendly Holiday Rentals in or Near Cook County
Apartment
10.0Exceptional
(198 Reviews)
1 Bedroom
1 Bath
2 Guests
151 ft²
- Kitchen
- Air Conditioner
- Pet Friendly
- Child Friendly
US $61/Night
7 Nights - US $426
Apartment
- Chicago
- ·
- Wrigleyville
- 0.22 mi to center
10.0Exceptional
(5 Reviews)
4 Bedrooms
2 Baths
10 Guests
1205.56 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $480/Night
7 Nights - US $3,361
Bed & Breakfast
8.0Excellent
(669 Reviews)
1 Bedroom
1 Bath
- Parking
- Internet
- Pet Friendly
- Security/Safety
US $218/Night
7 Nights - US $1,525
Apartment
10.0Exceptional
(176 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $447/Night
7 Nights - US $3,131
Apartment
- Chicago
- ·
- Belmont Cragin
- 0.48 mi to center
10.0Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
5 Guests
1345.49 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $284/Night
7 Nights - US $1,991
Apartment
- Chicago
- ·
- Roscoe Village
- 0.17 mi to center
10.0Exceptional
(103 Reviews)
2 Bedrooms
1 Bath
6 Guests
1200 ft²
- Parking
- Ocean View
- Balcony/Terrace
View
US $345/Night
7 Nights - US $2,413
Apartment
- Chicago
- ·
- Logan Square
- 0.48 mi to center
10.0Exceptional
(101 Reviews)
2 Bedrooms
1 Bath
5 Guests
850 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $180/Night
7 Nights - US $1,263
Apartment
10.0Exceptional
(87 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $153/Night
7 Nights - US $1,070
Apartment
10.0Exceptional
(70 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $450/Night
7 Nights - US $3,147
Large Holiday Rentals and Private Villas in Cook County
Over 1378+ Large Holiday Rentals and Private Villas in or Near Cook County
Apartment
- Chicago
- ·
- Brighton Park
- 0.39 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
1 Bath
10 Guests
1000 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $271/Night
7 Nights - US $1,894
Villa
- Chicago
- ·
- Hazel Crest
- 1.11 mi to center
10.0Exceptional
(5 Reviews)
4 Bedrooms
2 Baths
7 Guests
1097.92 ft²
- Parking
- Air Conditioner
- Pet Friendly
- Child Friendly
US $232/Night
7 Nights - US $1,624
US $857/Night
7 Nights - US $6,001
Apartment
- Chicago
- ·
- Little Village
- 0.68 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
1 Bath
12 Guests
1000 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $234/Night
7 Nights - US $1,639
Apartment
- Chicago
- ·
- Lake View East
- 0.18 mi to center
10.0Exceptional
(4 Reviews)
6 Bedrooms
2 Baths
20 Guests
3498.27 ft²
Private Beach- EV Charge Station
- Parking
- Ocean View
US $482/Night
7 Nights - US $3,371
Condo
- Chicago
- ·
- Elmwood Park
- 0.29 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
13 Guests
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $134/Night
7 Nights - US $935
Apartment
- Chicago
- ·
- River North
- 0.21 mi to center
9.6Exceptional
(35 Reviews)
2 Bedrooms
2 Baths
10 Guests
800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $265/Night
7 Nights - US $1,853
Apartment
- Chicago
- ·
- River North
- 0.21 mi to center
9.6Exceptional
(17 Reviews)
2 Bedrooms
1 Bath
10 Guests
1200 ft²
- Kitchen
- Air Conditioner
- Internet
- Child Friendly
US $205/Night
7 Nights - US $1,438
Villa
9.6Exceptional
(12 Reviews)
1 Bedroom
6 Baths
16 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $619/Night
7 Nights - US $4,334
Wheelchair Accessible Holiday Homes in Cook County
Over 3512+ Wheelchair Accessible Holiday Homes in or Near Cook County
Condo
10.0Exceptional
(64 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Oceanfront
- Breakfast
- Parking
- Ocean View
US $435/Night
7 Nights - US $3,042
Apartment
10.0Exceptional
(2 Reviews)
4 Bedrooms
4 Baths
10 Guests
1345.49 ft²
- Parking
- Air Conditioner
- Internet
- Child Friendly
US $434/Night
7 Nights - US $3,038
Bed & Breakfast
9.8Exceptional
(213 Reviews)
1 Bedroom
1 Bath
- Breakfast
- Kitchen
- Air Conditioner
- Internet
US $392/Night
7 Nights - US $2,746
Apartment
10.0Exceptional
(59 Reviews)
1 Bedroom
1 Bath
2 Guests
441 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $326/Night
7 Nights - US $2,284
House
- Chicago
- ·
- Near South Side
- 0.88 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
2 Baths
8 Guests
1797.57 ft²
- View
- Air Conditioner
- Internet
- Pet Friendly
US $441/Night
7 Nights - US $3,089
Apartment
- Chicago
- ·
- Downtown Chicago
- 0.42 mi to center
10.0Exceptional
(14 Reviews)
2 Bedrooms
3 Baths
8 Guests
2600 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $560/Night
7 Nights - US $3,919
Condo
- Chicago
- ·
- South Loop
- 0.68 mi to center
10.0Exceptional
(14 Reviews)
2 Bedrooms
2 Baths
4 Guests
689 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $359/Night
7 Nights - US $2,515
Apartment
- Chicago
- ·
- Printers Row
- 0.13 mi to center
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
7 Guests
1109 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $674/Night
7 Nights - US $4,717
Apartment
- Chicago
- ·
- West Loop Gate
- 0.20 mi to center
10.0Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $463/Night
7 Nights - US $3,241
Cook County Private Villas and Holiday Homes Under $200
Over 3922+ Cook County Private Villas and Holiday Homes Under $200
Apartment
10.0Exceptional
(64 Reviews)
1 Bedroom
1 Bath
3 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $187/Night
7 Nights - US $1,308
House
- Chicago
- ·
- Norwood Park West
- 0.52 mi to center
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
247.57 ft²
- Parking
- Balcony/Terrace
- View
- Kitchen
US $82/Night
7 Nights - US $574
House
- Chicago
- ·
- Bronzeville
- 0.16 mi to center
7.6Very Good
(126 Reviews)
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $176/Night
7 Nights - US $1,233
Apartment
- Chicago
- ·
- Edgewater Beach
- 0.16 mi to center
10.0Exceptional
(51 Reviews)
1 Bedroom
1 Bath
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $159/Night
7 Nights - US $1,110
Apartment
- Chicago
- ·
- South Loop
- 0.22 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
441.32 ft²
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $185/Night
7 Nights - US $1,295
Apartment
10.0Exceptional
(32 Reviews)
1 Bedroom
1 Bath
5 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $144/Night
7 Nights - US $1,006
Apartment
10.0Exceptional
(23 Reviews)
1 Bedroom
1 Bath
4 Guests
2900 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $187/Night
7 Nights - US $1,311
Apartment
- Chicago
- ·
- Mount Prospect
- 0.62 mi to center
10.0Exceptional
(23 Reviews)
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $183/Night
7 Nights - US $1,284
Apartment
- Chicago
- ·
- West Ridge
- 0.76 mi to center
10.0Exceptional
(17 Reviews)
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $177/Night
7 Nights - US $1,237
Instantly Bookable Holiday Homes in Cook County
Over 5642+ Instantly Bookable Holiday Homes in or Near Cook County
Apartment
- Chicago
- ·
- North Center
- 0.68 mi to center
10.0Exceptional
(153 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $228/Night
7 Nights - US $1,598
House
- Chicago
- ·
- Hoffman Estates
- 3.50 mi to center
10.0Exceptional
(10 Reviews)
1 Bedroom
1 Bath
2 Guests
2800 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $51/Night
7 Nights - US $359
Apartment
- Chicago
- ·
- Magnolia Glen
- 0.09 mi to center
10.0Exceptional
(123 Reviews)
2 Bedrooms
2 Baths
5 Guests
1650 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $577/Night
7 Nights - US $4,042
Apartment
10.0Exceptional
(89 Reviews)
1 Bedroom
1 Bath
3 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $251/Night
7 Nights - US $1,756
Apartment
- Chicago
- ·
- Sheffield Neighbors
- 0.18 mi to center
10.0Exceptional
(87 Reviews)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $311/Night
7 Nights - US $2,177
Apartment
- Chicago
- ·
- Andersonville
- 0.33 mi to center
10.0Exceptional
(83 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $249/Night
7 Nights - US $1,740
Apartment
- Chicago
- ·
- Rogers Park
- 0.64 mi to center
10.0Exceptional
(64 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $390/Night
7 Nights - US $2,729
Condo
10.0Exceptional
(63 Reviews)
2 Bedrooms
2 Baths
5 Guests
1200 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $210/Night
7 Nights - US $1,468
Apartment
- Chicago
- ·
- North Center
- 0.08 mi to center
10.0Exceptional
(61 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $450/Night
7 Nights - US $3,150
Book a Last Minute Place to Stay in Cook County
About Casai's Private Villas and Holiday Rentals in Cook County
Discover more than 10025 vacation rentals available in Cook County. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Cook County.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Cook County, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Cook County. On average, places to stay near Cook County offer 728.86 ft², with nightly prices averaging US $375.
With Casai, finding and comparing holiday rentals in Cook County is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Cook County
| Type | Count |
|---|---|
| Holiday Apartments | 5755 |
| Vacation Homes | 2112 |
| Villas | 19 |
| Cottages | 14 |
Use these Quick Filters to Find a Holiday Rental in Cook County
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Cook County.
Weather in Cook County, IL
View the weather forecast for Cook County before booking your Cook County Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Cook County, IL
Casai offers a large selection of top attractions around Cook County . Research things to do on your vacation before you visit Cook County.
Other Places to Stay in Cook County, IL
Frequently Asked Questions About Cook County?
What are the top holiday rentals in Cook County?
With numerous options available in Cook County, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Cook County:
- The Sono Chicago
- 52nd Floor MagMile Penthouse Views Fireplace Pool
- Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
- 3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
- King Bed Non-Smoking
- Remodeled, spacious and bright apartment — near Loyola, beach & subway
- 51st Floor MagMile Penthouse Views Balcony Pool
- NEW LUXURY PENTHOUSE CONDO
- NEW LUXURY CONDO WITH PATIO DECK
- Full Bed | Non Smoking
How many holiday rentals have private pools in Cook County?
Discover a selection of holiday rentals with private pools near Cook County with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Stylish River North Suites Luxe Comfort Near Chicago’s Best Shopping & Nightlife
- Lux Apts with Lake Views and Top Amenities
- Stay One Chicago
- Chic Stay in River North: Luxury Suites, Top Amenities, Near Arts & Nightlife!
Which holiday homes in Cook County are best for families?
If you're searching for a family-friendly holiday home in Cook County, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Cook County:
- Best Lincoln Square Location - Spacious 2 bedroom
- The Brown House - A luxurious UChicago Campus stay
- Wrigleyville Inn
How many Casai.nz holiday rentals are available in Cook County?
As of 2026, Casai boasts over 10025 properties listed in the Cook County area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Cook County.
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