
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.

RetroModern Bungalow | pet friendly | free parking
Experience the city in style at Retro Modern Bungalow, the perfect pad for up to four friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fenced-in, 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 and/or catch the train a few blocks away.

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!

Round Lake Getaway Retreat
Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Elmhurst NEW - Super Clean Modern Farmhouse!
Not your average Air BNB!!! 🏡 Newly renovated - CLEAN modern farmhouse in a great location! ✨ ✅Pet Friendly! 🐕 ✅15 min from O'hare. ✈ ✅25 min to Downtown Chicago 🏦 ✅Close to Grocery, restaurants, coffee, shopping, golf, expressways, down town Elmhurst ,Train and Oakbrook and Fashion Outlet Mall. ✅3 great sized bedrooms, 2 living area sofas converts into sleepers ✅Smart TV in family room and Master. ✅ Back patio with dining and seating ✅Large fenced in yard.

Division St Designer Home In Heart of Wicker Park
Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).

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, 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!

Cozy Home in Brookfield
Discover tranquility just minutes from the busy city life! Nestled in the heart of Brookfield, IL, our charming home offers the perfect blend of suburban serenity and urban convenience. Just an 8-minute walk from the train station, you'll find easy access to downtown Chicago while enjoying the peaceful atmosphere of our neighborhood. Max 4 overnight guests. No parties or events. Pets allowed (no exotic pets or animals with a bite history).

Modern Boho house in Lombard 7 min to Metra
Kick back and relax in this calm, stylish space. Visiting family in Chicagoland area? Traveling for work? Lombard is centrally located 30 min to everywhere! The house is only 6 min to Oakbrook Shopping and Business Center and upscale shopping and fabulous restaurants like RH with rooftop restaurant, 8 min to Yorktown Shopping Center. Whatever your travel purpose is, we will be happy to host you! Welcome home!

Lockports Famous Hideaway ~ 2bdrm Guest House Flat
A history buff’s dream filled with antiques & artifacts relating to Chicago, Joliet, Lockport, the I & M Canal & "Route 66"! Family & Business Friendly. 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. Private-entrance/self-check-in. Have a 'historic' stay at the "Hideaway"! Can accommodate up to 6 guests.

Romantic Escape ~ Adult Playhouse w Exotic Dungeon
“What a great time we had, reconnecting and enjoying each other. We came back home in such a better place than we where when we left.” 🌹More than a stay — a private, immersive romantic experience crafted exclusively for adult couples who want something unforgettable, intimate, and truly one-of-a-kind.

King bed, dog friendly, right by O'hare airport!
This luxurious home is close to everything, making it easy to plan your visit. It is located minutes away from O’hare Airport, Rivers Casino, Rosemont restaurants and a short drive/train ride to Chicago. Stay in this beautifully renovated home and you will truly feel like you’re on vacation.

Remodeled | Game room | Fire Pit | 5 Min to Zoo
➜ Fully remodeled 3 bedroom 2 bath home with modern finishes ➜ Spacious double-lot backyard with fire pit, pergola, dining/seating areas, and grill ➜ Smart TVs in every room ➜ Game room with arcade, foosball, and board games ➜ Fast speed internet ➜ 5 minutes away from Brookfield Zoo
Popular amenities for Countryside house rentals
House rentals with a pool

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

Pool, 30 mins to CHI, 3 Kings, Outdoor Space, BBQ

The Fox River Farmhouse-walk to downtown and pool

Paradiso Vacation

Backyard Paradise/ Private Pool + Peaceful Stay

A Glass House in a Gated Nudist Community

Crystal Lake 4BR | Insurance & Repair Stays

Paradise with Pool & Games
Weekly house rentals

3BR/2BA + Pull Out Sofa Bed + No Stairs + Backyard

Spacious Home in Chicago Suburbs

Cozy Estate 20 Minutes from Downtown and Lakefront

At the center of it all, a secret suburban gem!

Grand Retreat/5Brs/Game Room

Homey Brookfield Gem — 4 Beds, 2 Baths, Great Yard

Cozy 5BD Home with Scandinavian Vibes

Watch fireworks from backyard
Private house rentals

The Architectural Haven

Modern 2Bdrm Westchester/Chicago Home.With Hot tub

Garden Suite 10 Min to O’Hare w/ Yard & Grill

The Lyons Den

Lakefront View Getaway Home! Hot tub! Kayak!

Three Kings Chicago. Royal experience. Cloud beds!

Villa Park Getaway – Cozy 3BR Retreat Near Chicago

Bliss in Brookfield- 5BR, 3BA, Fenced Yard
Destinations to explore
- Chicago Vacation rentals
- Indianapolis Vacation rentals
- Columbus Vacation rentals
- St. Louis Vacation rentals
- Louisville Vacation rentals
- Cincinnati Vacation rentals
- Detroit Vacation rentals
- Milwaukee Vacation rentals
- Traverse City Vacation rentals
- Des Moines Vacation rentals
- Downtown Chicago Vacation rentals
- Ann Arbor Vacation rentals
- Wrigley Field
- Lincoln Park
- United Center
- Soldier Field
- Grant Park
- Navy Pier
- Millennium Park
- Indiana Dunes State Park
- 875 North Michigan Avenue
- Naval Station Great Lakes
- Six Flags Great America
- The Field Museum
- Shedd Aquarium
- Humboldt Park
- Chicago River Walk
- University of Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Loyola University Chicago
- Donald E Stephens Convention Center
- Frank Lloyd Wright Home and Studio
- Union Park
- Garfield Park Conservatory
- Illinois Beach State Park





