A rustic barn in a lush green field with tall trees and a clear sky.

Countryside Vacation Rentals

Q: What are some of the best vacation rentals that Countryside has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line : This vacation home rental near Countryside is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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Dates

November 2026

December 2026

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Our top choices for Countryside vacation rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Downtown Chicago

Jeff

AED 803 total

includes taxes & fees

12 Nov - 13 Nov

A waterfront promenade with high-rise buildings, a sandy beach, and a pedestrian walkway.

2. Kasa Lake Shore Chicago

Downtown Chicago

Jair

AED 882 total

includes taxes & fees

22 Nov - 23 Nov

A modern kitchen with a large island, bar stools, and a city view.

3. Level Chicago – Old Town

Downtown Chicago

Robert Edward

AED 828 total

includes taxes & fees

23 Nov - 24 Nov

A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

4. Vibrant House, Walk to Train, Game Room

Brookfield

Chasity D.

AED 2,471 total

includes taxes & fees

16 Nov - 17 Nov

A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

5. Wrigleyville Suites

Lakeview

Francisco

AED 507 total

includes taxes & fees

12 Nov - 13 Nov

A dining area with a table set for two, a black leather sofa, and a ceiling fan.

6. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

Berwyn

Cynthia M.

AED 648 total

includes taxes & fees

16 Nov - 17 Nov

A compact kitchen with dark wood cabinets, stainless steel appliances, and a dining area with a wooden table and chairs.

7. Cozy, Comfortable and Convenient apartment. Close to everything!

Oak Park

Alicia K.

AED 1,039 total

includes taxes & fees

16 Nov - 17 Nov

A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

8. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Westmont

Tomas R.

AED 946 total

includes taxes & fees

12 Nov - 13 Nov

A two-story house with a brick exterior, a sloped roof, and a front porch.

9. At Home in Oak Park

Oak Park

Melissa

AED 1,264 total

includes taxes & fees

12 Nov - 13 Nov

A modern living room with teal sofas, a coffee table, and a TV.

10. Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Northlake

Kaitlyn W.

AED 637 total

includes taxes & fees

15 Nov - 16 Nov

A modern living room with a blue sofa, a patterned rug, and a television.

11. Great Area Logan Square Apt Games Pets - Sleeps 5

Avondale

Deborah J.

A modern living room with a flat-screen TV, a sofa, a coffee table, and a dining area with a bar stool.

12. 3BR Complete and Spacious Apartment in Ideal Spot

West Town

Francis

AED 814 total

includes taxes & fees

16 Nov - 17 Nov

A living room with a television displaying 'NETFLIX,' a dining area with a table and chairs, and a sofa.

13. Perfect 2-bedroom apartment in lovely Berwyn for your stay

Berwyn

AED 965 total

includes taxes & fees

15 Nov - 16 Nov

A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.

14. Chic Urban Retreat Near Wrigley Field w/Parking

Lakeview

Rachael

AED 1,573 total

includes taxes & fees

30 Nov - 1 Dec

A rooftop terrace with a brick wall, large windows, and a metal railing.

15. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Uptown

Michael S.

AED 1,137 total

includes taxes & fees

14 Nov - 15 Nov

A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

16. Historic Oak Park Home

Oak Park

Janette

AED 1,309 total

includes taxes & fees

16 Nov - 17 Nov

Two twin beds in a hotel room with a green accent wall, a framed picture, and a nightstand with a lamp.

17. 2 Full Beds | Non-Smoking, Kitchen

Chicago

Anonymous traveler

AED 306 total

includes taxes & fees

9 Dec - 10 Dec

A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

18. LUXE 3 BR, 2 BA + Hot Tub

Elmhurst

Brenda M

AED 1,293 total

includes taxes & fees

16 Nov - 17 Nov

A neatly arranged bedroom with a bed, bedside tables, and abstract wall art.

19. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park

rebecca

AED 598 total

includes taxes & fees

15 Nov - 16 Nov

20. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Uptown

Paul J.

AED 927 total

includes taxes & fees

12 Nov - 13 Nov

View all properties

Find vacation rentals that suit your style

Top Countryside Hotel Reviews

A hotel room with two beds, a desk with a television, a chair, and a window with curtains.

Best Western Plus Chicagoland - Countryside

Countryside

10/10 Excellent

Brandon

A restaurant with a long counter, booths, and hanging light fixtures.

William Tell Hotel MOD Collection by Sonesta

Countryside

10/10 Excellent

Ronald

A spacious dining area with multiple tables and chairs, large windows with a view of the city, and a modern ceiling design.

SureStay Plus Hotel by Best Western Chicago Lombard

Highland Hills

10/10 Excellent

Margaret

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

L7 CHICAGO by LOTTE HOTELS

Downtown Chicago

10/10 Excellent

Erin

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

10/10 Excellent

Jennifer

A dining table set for six with a cityscape view through large windows.

Swissotel - Chicago

Downtown Chicago

10/10 Excellent

Brian

A modern interior with a geometric light wall, a staircase, and hanging crystal chandeliers.

Hampton Inn & Suites Chicago Downtown

Downtown Chicago

10/10 Excellent

Shatani

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

10/10 Excellent

blerina

The Intercontinental hotel facade with a large American flag and a floral display.

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

10/10 Excellent

Rosemary

A cityscape at dusk with high-rise buildings, including a Hilton hotel.

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

10/10 Excellent

I was traveling with two 14 year olds on a business/vacation trip and we stayed here for five days. The location is great. I wanted a hotel that was convenient to the major attractions and downtown, and safe for the boys to walk around on their own. We were able to walk to Navy Pier, Millennium Park, the Loop, and the Hancock Building. It's a good 20-25 minute walk to Navy Pier, but you walk along Lakeshore Drive and it's very enjoyable. The property is very nice, although we didn't get the two...

Joanna

An outdoor rooftop lounge with seating, planters, and a view of surrounding high-rise buildings.

Hampton Inn Chicago West Loop Fulton Market Area

Downtown Chicago

10/10 Excellent

We will definitely be staying here again! Great location, clean room, and great service. They even have a great complimentary breakfast which is a must have in a city like Chicago. The staff was great also. We had to switch trains for an earlier one due to weather and got into Chicago in the AM. Check in is 4pm and with two small children we were worried about what to do for hours but the staff helped us out and luckily had a room available.

Alexander

A hotel lobby with a bar area, a chandelier, and a reception desk.

Residence Inn Chicago Downtown/Loop

Downtown Chicago

10/10 Excellent

Sergio

A hotel with a modern glass facade, signage for SpringHill Suites, and a well-lit entrance.

Springhill Suites by Marriott Chicago Downtown/ River North

Downtown Chicago

10/10 Excellent

Recently stayed at the Springhill Suites/River North. Could not have picked a better location for the first time in Chicago. Tons of local dining options. Close to landmarks. Easily walked to the Magnificient Mile(Michigan Ave) Walked to the subway to go to Wrigley Field and the United Center. Hotel was excellent. Clean, the staff was excellent in all areas. Free breakfast was fresh and good. Highly recommend overall.

Michael

A modern urban building with a distinctive curved facade, a prominent '10pin' sign, and a 'Tertius' restaurant on the ground floor.

Hotel Chicago Downtown, Autograph Collection by Marriott

Downtown Chicago

10/10 Excellent

Abdullah

A hotel room with a large window offering a city view, a bed, a desk, and a chair.

Courtyard by Marriott Chicago Magnificent Mile

Downtown Chicago

10/10 Excellent

Forever one of my favorite hotels and one of my two favorite Courtyard properties I've ever stayed at! This is the 3rd year in a row we've stayed here when coming to Chicago and it never disappoints. It feels like a high-end hotel for an affordable price (considering where it is)! The staff is great super helpful, rooms are so clean and overall just is one of the nicest places! Highly recommend if you're looking for a spot in Chicago!

adriana

A hotel entrance with a glass door, a sign above the door, and two potted plants on either side.

Hampton Inn Majestic Chicago Theatre District

Downtown Chicago

10/10 Excellent

Anne

Frequently Asked Questions

Can I find vacation rentals in Countryside?

Yes, we offer vacation rentals close to the most popular local attractions in Countryside, or you can select a secluded option if you'd like a relaxing place to stay. Visitors like the top-notch restaurants and shops in Countryside. Make sure you have time to check out the live music and zoo during your trip.

What are some of the best vacation rentals that Countryside has to offer?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This vacation home rental near Countryside is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Countryside?

Explore the area and family-friendly sights such as Childrens Museum of Oak Lawn, or get out into nature at a spot like Millennium Park. In the larger area, you’ll find popular places like Soldier Field and Navy Pier.

What are vacation rentals like in Countryside?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Countryside. Vacation rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for families.

Countryside Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Countryside vacation rentals

1. Sentral Michigan Avenue

2. Kasa Lake Shore Chicago

3. Level Chicago – Old Town

4. Vibrant House, Walk to Train, Game Room

5. Wrigleyville Suites

6. Private Parking/Comfy Bed/25mins to ORD>MDW>DT>HOSP

7. Cozy, Comfortable and Convenient apartment. Close to everything!

8. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

9. At Home in Oak Park

10. Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

11. Great Area Logan Square Apt Games Pets - Sleeps 5

12. 3BR Complete and Spacious Apartment in Ideal Spot

13. Perfect 2-bedroom apartment in lovely Berwyn for your stay

14. Chic Urban Retreat Near Wrigley Field w/Parking

15. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

16. Historic Oak Park Home

17. 2 Full Beds | Non-Smoking, Kitchen

18. LUXE 3 BR, 2 BA + Hot Tub

19. Hyde Park Trendy Studio Apartment in Good Spot

20. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Find vacation rentals that suit your style

Top Countryside Hotel Reviews

Best Western Plus Chicagoland - Countryside

10/10 Excellent

Frequently Asked Questions

Can I find vacation rentals in Countryside?

What are some of the best vacation rentals that Countryside has to offer?

What can I see and do in Countryside?

What are vacation rentals like in Countryside?