
House vacation rentals in Countryside
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Top-rated house rentals in Countryside
Guests agree: these houses are highly rated for location, cleanliness, and more.

Lockports Famous Hideaway ~ 2bdrm Guest House Flat
A history buff’s dream filled with antiques & artifacts relating to Lockport, Chicago, Joliet, I & M Canal & "Route 66"! If you have roots in Illinois or Lockport, the Hideaway is for you! The entire upstairs 1,500 sq ft vintage 2 bedroom house apartment is all your own space. The flat is NOT shared with other guests/host. Family & Business Friendly. Private-entrance/self-check-in. *Can accommodate up to 6 guests. Extra charges apply after 2 guests. Have a 'historic' stay at the "Hideaway"

Chicago River House -BBQ Oasis now open!
Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

Retro Modern Bungalow | fire pit | free parking
Experience the city in style at our Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Modern Victorian Charm | A+ Location in OP
Your family will be close to everything when you stay at this centrally-located Victorian home in the heart of the historic Frank Lloyd Wright district. The walkable location is perhaps one of the best features of this newly updated Victorian. Walk to local restaurants, coffee shops, ice cream and parks. This vacation rental is steps away from the FLW studio and Hemingway museum. Free parking. Steps from the Metra or CTA line. 15 minute drive to downtown Chicago. 22 minute drive to airport.

Dog Friendly Cozy North Naperville 3 BED/2 BA Home
Welcome to the Naperville Nest! Rare North Naperville opportunity to find a home suited for the whole family! Pets are more than welcome to enjoy the 1/2 acre fully fenced in yard. This is a a fully updated home minutes from Downtown Naperville, I-88 and many more exciting destinations in the Western Suburbs. You will feel at home whether you're inside or outside...each bedroom has it's own TV and the outdoor living includes natural gas firepit & grill/dining table...this home has it all!

Charming dog friendly 2-Bath Bungalow Near Chicago
Steps from the cobblestone streets of Forest Park into our cheery bungalow, perfect for artistic souls and business travelers alike. Inside is a design savvy mix of mid-century furniture, comfy beds, and art from around the globe. Built in 1908, it boasts modern amenities you desire without sacrificing vintage charm. Minutes away from local shops, restaurants. Just off I-290, Blue Line CTA, 20. min drive to ORD, Midway & Downtown Chicago. Plus we’re dog-friendly-- bring up to 2 pups!

Safe, Clean, Central Location & Parking, Sleeps 4
Our Oak Park, recently remodeled garden unit is 3 blocks to the train with free parking in upscale, safe, walkable Oak Park. Enjoy some time in our little urban farm. Check out the gardens and visit our 6 friendly hens. This non-smoking studio with a kitchenette is perfect for tourists, families, or business travelers. We require no check-out chores. Easy highway and airport access. No parties, 4 guests max. Booking age, 25 or at least one 5 ⭐️ review. Visit profile for more units.

Jacuzzi, King Beds, Easy Access to DT Chicago!
Our 4bd, 2.5ba house is perfect for a group of friends or family looking for a clean, modern place in a wonderful neighborhood. There is plenty of space for 10 people to sleep comfortably (4 beds), as well as 4 smart TVs (w/ complimentary Hulu & Disney+), a deck w/ a pergola, built-in grill, & firepit, a large fenced backyard, a game room (w/ ping pong and more), a jacuzzi, an office space, & much more. Great access to City of Chicago by I-290, as it's directly west of Downtown!

Games, Grounds, Goodness in DG
Our family loves games and when travelling it is great to have entertainment for the whole family. Our game room includes a video arcade game with over 400 options, boardgames and more! Maybe simple cards or puzzles are your preference--we have them all in this fully furnished home with large backyard to play in. Bedroom 1--bunk bed with full on bottom, twin on top Bedroom 2--queen bed with room for a play pen Stay for a weekend or longer and know fun will be had!

“Aunt Betty’s Cottage” whimsical enclosed yard
Perfect for 1 - 4 in quaint Westmont. Decor is vintage chic with a focus on retro arts and collectibles. Cozy blankets and whimsical art adorn the walls. Perfect for folks who love cute quaint CLEAN and comfy not Kondo! A place to call home where the barn door closes off the Living room. A dinner for 6 in the quaint dining area. Laundry room in the home. New Grill for Summer 2024, out door furniture. Beyond pet friendly we have many accessories for Dogs.

The Brookfield Breakaway w/ Game Room
This stylish place to stay is perfect for group trips. This split level home has an open concept living room and dining room combo. The gorgeous kitchen has exceptional attention to detail. There are three bedrooms and one bathroom upstairs. Downstairs you’ll find a master suite equipped with its own living space and en suite bathroom. Relax outside on our sectional and enjoy BBQ time with your loved ones. There’s enough space for everyone to enjoy.

Quiet cul-de-sac with huge fenced in backyard
3 bedroom, 2 bath ranch home on a quiet cul-de-sac. Big fenced in backyard for the kids, dog, & adults to play during the day, then relax by the fire at night. Walking distance (50 ft.) to the bar/restaurant with private entrance. 15 miles (25 mins) from downtown Chicago. And for you couples, come back home from your busy day, sit back and relax in the 8 jet jacuzzi whirlpool tub that will comfortably fit both of you.
Popular amenities for Countryside house rentals
House rentals with a pool

After-Dune Delight! Large Home with Pool and Fun f

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Comfy 3BR 2BA, Liv+Fam Rm, Prime, 3-Car Parking

Chic Fulton Market Oasis + Curated Comfort & Style

Munster hide away

Spacious 3 Floor Townhome

Family-Friendly Suburban Getaway Near Chicago

Friends-Inspired Vintage Vibes House near Chicago
Weekly house rentals

Beachfront-Lake Michigan-Indiana Dunes-5BD/3BR

Spacious Designer Oasis: Game Room - Yard - Garage

The Architectural Haven

Casa 22 | Luxury Modern House for 6 | 3 Bed,2 Bath

A Comfortable Stay While You are Away in Oak Park

Cozy getaway in the city.

Lux Stay Sleeps 8: DT Geneva

Spacious Home-Great Lakes Close-Quiet Location
Private house rentals

Cute & Cozy Westmont, IL House Near the Best Areas

Boutique Charmer Brookfield/La Grange

Bliss in Brookfield- 5BR, 3BA

The Sunshine Spot

Worth It! 3 bedroom ranch home

Sauna • Modern • 2 blocks to Beach • Game Room

The Maple Place

Charming Home in Westmont, Close to Chicago!
Destinations to explore
- Chicago Vacation rentals
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- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- 875 North Michigan Avenue
- Humboldt Park
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Museum of Science and Industry
- Brookfield Zoo
- Illinois Beach State Park
- Willis Tower
- The Beverly Country Club
- Raging Waves Waterpark
- The 606
- Olympia Fields Country Club