
Countryside Holiday Rentals
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
Our top choices for Countryside holiday rentals

1. Wrigleyville Suites
Wrigleyville Suites
2. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP
3. Kasa Lake Shore Chicago
Kasa Lake Shore Chicago
4. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
5. Great Area Logan Square Apt Games Pets - Sleeps 5
Great Area Logan Square Apt Games Pets - Sleeps 5
6. Chic Urban Retreat Near Wrigley Field w/Parking
Chic Urban Retreat Near Wrigley Field w/Parking
7. Chic Suite/Mins to L Train /Laundry/Free Parking
Chic Suite/Mins to L Train /Laundry/Free Parking
8. Studio Near Wrigley • Sleeps 4 • Games • Fireplace
Studio Near Wrigley • Sleeps 4 • Games • Fireplace
9. 2 Full Beds | Non-Smoking, Kitchen
2 Full Beds | Non-Smoking, Kitchen
10. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
11. Cozy studio in Andersonville Chicago
Cozy studio in Andersonville Chicago
12. Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park Trendy Studio Apartment in Good Spot
13. Vibrant House, Walk to Train, Game Room
Vibrant House, Walk to Train, Game Room
14. Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
Peaceful Cozy Beach View| 13 mins DT | 4 mins Lake
15. 3BR Complete and Spacious Apartment in Ideal Spot
3BR Complete and Spacious Apartment in Ideal Spot
16. Level Chicago – Old Town
Level Chicago – Old Town
17. King Bed Non-Smoking
King Bed Non-Smoking
18. Air-Conditioned King Suite | Complimentary Breakfast
Air-Conditioned King Suite | Complimentary Breakfast
19. Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
20. 1BR/1BA City Comfort
1BR/1BA City ComfortFind holiday rentals that suit your style
Top Countryside Hotel Reviews

L7 Chicago by LOTTE
Find out more about Countryside
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Countryside holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Countryside. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Countryside. Seeing all the best attractions is bound to make you fall in love with Countryside. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Countryside short-term rentals, that won’t be hard to do.




































































