Skip to content
Sign up
Log in
Vacation rentals in Countryside

Vacation rentals in Countryside

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Countryside

Guests agree: these stays are highly rated for location, cleanliness, and more.

Hip Chicago Apartment - FREE Parking Spot Included
SUPERHOSTEntire flat · 4 guests · 2 beds · 1 bathroom
Hip Chicago Apartment - FREE Parking Spot Included

You’ll love this high-end, newly renovated 2 bedroom apartment located in Chicago’s iconic Logan Square. This bright and modern space has free parking, a fully equipped stainless-steel kitchen and an outdoor sitting area perfect for a sunny meal. Walking distance from a bike rental station and hip Armitage Street where you can find a wide selection of restaurants and bars to suit any palate. You’ll also be close by the 606 Trail, a lovely place to enjoy a walk, bike or go for a run

What guests are saying:

“I really enjoyed my stay at Alex and Leo’s place. Check-in was a breeze, great communication from the hosts, the bed was super comfortable, kitchen had all the necessary items, great TV, and comfy sofa, and the location is excellent with lots of fun places to walk. I highly recommend this place.”

Checkerboard Studio with Private Outdoor Hot Tub and Yard
PLUSEntire flat · 2 guests · 1 bed · 1 bathroom
Checkerboard Studio with Private Outdoor Hot Tub and Yard

Soak in the private outdoor hot tub in the leafy, fenced-in yard outside this spacious studio. The home boasts high ceilings with exposed silver ducting and eclectic decorations, including cow print furniture, and an intricately carved bathroom door. While the decor is eclectic, the king-size bed sets the standard for comfort. The Checkerboard Studio is perfect for a cozy getaway and offers intimacy, but with enough space to move. Functional kitchen is well supplied and easily navigated. If the outdoor hot tub doesn't appease your need for bubbles, the jetted tub and shower stand ready.

What guests are saying:

“The stay was great! The hot tub and back patio with grill was excellent and made it really feel like we were on vacation. The bed was super comfortable, I loved the artful touches around the apartment, and the neighborhood was really cute and quiet. I appreciated how responsive Brad was during check-in and check-out, would highly recommend.”

Clean & Bright Chicago Condo - FREE Parking Spot
SUPERHOSTEntire flat · 4 guests · 2 beds · 1 bathroom
Clean & Bright Chicago Condo - FREE Parking Spot

Enjoy your restful stay at this chic, yet comfortable 2 bedroom condo located in Chicago’s iconic Logan Square. This newly renovated unit offers free parking for one car as well as a beautiful, fully functional, updated kitchen with a dining table for you to enjoy cooking a meal or ordering in. You will be within walking distance of a bike rental station as well as the 606 Trail, a picturesque place to take a bike ride, walk or quick run.

What guests are saying:

“Leo&Alex communicated beautifully from the moment we booked. The space is just as the photos advertise. The space was clean, the neighborhood is adorable and close to everything. We would love to come back .”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Countryside holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Countryside

Unwind in the Bath at a Hip, Historic Coach House
PLUSEntire guest house
Unwind in the Bath at a Hip, Historic Coach House
Price:₹7,392 / night
Clean, Comfy & Private Studio Space
SUPERHOSTEntire guest suite
Clean, Comfy & Private Studio Space
Price:₹6,123 / night
Private floor with living room and office space
SUPERHOSTPrivate room
Private floor with living room and office space
Price:₹1,931 / night
Cosmopolitan nest in Oak Parks North Side
SUPERHOSTEntire flat
Cosmopolitan nest in Oak Parks North Side
Price:₹3,733 / night
Private Room/Bath Wicker Park, Free Street Parking
SUPERHOSTPrivate room
Private Room/Bath Wicker Park, Free Street Parking
Price:₹3,019 / night
Contemporary Oak Park Loft
SUPERHOSTEntire loft
Contemporary Oak Park Loft
Price:₹4,557 / night
Clarendon
SUPERHOSTEntire house
Clarendon
Price:₹11,125 / night
Garden Apt private entrance über safe neighborhood
Entire flat
Garden Apt private entrance über safe neighborhood
Price:₹4,107 / night
Cozy place close to downtown Chicago!
SUPERHOSTEntire flat
Cozy place close to downtown Chicago!
Price:₹4,747 / night
A private cozy place with free parking!
Private room
A private cozy place with free parking!
Price:₹2,934 / night
Sunny Jumbo Studio in the Heart of Oak Park
SUPERHOSTEntire flat
Sunny Jumbo Studio in the Heart of Oak Park
Price:₹6,667 / night
G1. Best location and most affordable! So much fun
SUPERHOSTPrivate room
G1. Best location and most affordable! So much fun
Price:₹2,347 / night
Show all