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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.

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Top guest favorite

A welcoming hallway showcases a vintage console table with a lamp, next to a wall-mounted map. A bookshelf filled with books emphasizes the space's charm. Soft light filters through a doorway leading to a cozy living area that features a partially visible round rug and dining table.

Home in Lockport

4.96 out of 5 average rating, 151 reviews

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"

A charming single-story brick house with a welcoming front porch. The entrance features a set of steps leading up to a white door, surrounded by large windows that allow natural light to enter. A well-maintained yard is adorned with fallen leaves.

Home in Whiting

4.96 out of 5 average rating, 131 reviews

MiniGolfHouse-Chicago Close Beach & Indoor Fun!

🌆 30min drive to downtown Chicago ⭐️ Near Horseshoe Casino, Lake Michigan, Whihala Beach, Whoa Zone ⛳️ Heated basement with mini golf, arcade games and big TV 🐶 Pet fee: $150 (Must let us know BEFORE BOOKING if bringing a pet) ⭐️ Close To: Wolf Lake, Indiana Dunes, HardRock 🏠 cots, air mattress, futon sofa in basement 🍼 pack & play, high chair avail ❤️ Guests love: -short drive into Chicago -comfortable beds -indoor mini golf -nearby shops & food -heated bidet toilet seats

Top guest favorite

4.98 out of 5 average rating, 163 reviews

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.

The exterior of a single-story home is framed by lush green grass and dark mulch landscaping. A welcoming pathway leads to the front door, adorned with a seasonal wreath. A large tree provides shade, and a white fence marks the boundary of the yard.

Home in Naperville

4.86 out of 5 average rating, 138 reviews

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 storefronts line a vibrant street, showcasing a mix of architectural styles. Outdoor seating under colorful umbrellas offers a welcoming atmosphere for passersby. Various shops and restaurants contribute to a lively urban scene set against a clear blue sky.

Home in Forest Park

4.91 out of 5 average rating, 302 reviews

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!

Top guest favorite

Home in Oak Park

4.97 out of 5 average rating, 147 reviews

Garden: 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.

Top guest favorite

Home in Westchester

4.97 out of 5 average rating, 112 reviews

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!

Top guest favorite

A charming red cottage is nestled in a lush green yard, surrounded by tall trees. A tire swing hangs from a large oak, and a set of blue lawn chairs is positioned near the riverbank, providing an inviting space to relax and enjoy nature.

Home in South Elgin

4.97 out of 5 average rating, 259 reviews

Rustic River House W/Firepit, Tire Swing & Grill

Fall is in the air!! Come visit our family's wonderful riverfront cottage, ready and waiting. A two bedroom 750 sqft house with 1 bathroom on just under an acre property. A special place to relax, do some fishing, grilling, and roasting marshmallows on the fire. Located in a secluded unincorporated Fox River neighborhood in Kane County just a half mile from Blackhawk waterfall via bike path. The subdivision is hidden between the Jon J. Duerr and Blackhawk forest preserves.

Top guest favorite

A spacious home is set on a grassy lawn surrounded by trees. The house features a charming exterior with large windows and a covered porch. Edges of the yard are defined by neatly trimmed hedges, creating a welcoming environment for relaxation.

Home in Carol Stream

4.92 out of 5 average rating, 113 reviews

LakeHouse Stay! Hot Tub-Bar-Kayak-pool table-darts

Our beautiful home is the perfect place to gather with friends & family, relax, refresh, fish, have fun with your loved ones. It's the perfect home away from home with great views of the lake and on a quiet cul-de-sac. Stunning views of the lake while grilling or the firepit from the completely upgraded patio & the hot tub 🥂 🐶Up to 2 furry babies are allowed & they'll love the almost 1 acre fenced-in yard! (pet fee is extra & must be included at time of booking)

The image presents a two-story home with framed cedar bevel siding. A welcoming front porch features wooden railings and steps leading to the entrance. Surrounding greenery adds a natural touch, while the well-maintained pathway and lawn contribute to the property’s inviting exterior.

Home in Blue Island

4.82 out of 5 average rating, 214 reviews

Warm and comfortable inviting Suburban home !

160 year old land mark community, Framed cedar bevel siding 2 story home, front porch , 10 ft high ceilings, kitchen canned lighting home. 6 feet fence In closed yard, whole house water filtration system , Quite neighborhood with sidewalks . 19 miles to downtown Chicago , Metra train station and bus route, in walking distance . driving to the city of Chicago 5 minutes to major expressways . Host is willing to be available for any and all information 24/7.

An open concept living and dining area features a blue sectional sofa paired with a round coffee table on a patterned rug. A sleek TV stand displays a scenic image. A dining table with black chairs and a chandelier is visible in the background, enhancing the space.

Home in Brookfield

4.88 out of 5 average rating, 113 reviews

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.

A corner jacuzzi whirlpool tub is positioned against a wall, featuring multiple jets for relaxation. A white toilet and a small wooden stool are visible nearby. Light gray walls are complemented by a window covered with a light-colored curtain, allowing natural light to filter in.

Home in Chicago Ridge

4.92 out of 5 average rating, 161 reviews

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.

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Hotels

Stylish accommodations with great services and amenities

Popular amenities for Countryside house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

An outdoor pool is surrounded by wooden decking and a fence, offering a private swimming area. Lush trees provide shade, while a clear sky with soft clouds hangs above. The pool is filled with blue water, and a few inflatable toys float on the surface.

Home in Schererville

4.93 out of 5 average rating, 72 reviews

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

4.89 out of 5 average rating, 9 reviews

Harbor Inn - Canal Port

Home in Fulton Market

4.67 out of 5 average rating, 18 reviews

Chic Fulton Market Oasis + Curated Comfort & Style

A living room is presented with light wooden flooring and a soothing grey wall. Two red sofas are arranged for seating, facing a wall-mounted television. Natural light filters through two textured window shades, and a lamp stands beside the furnishings, adding to the room's cozy layout.

Home in Schaumburg

4.74 out of 5 average rating, 31 reviews

Spacious 3 Floor Townhome

Home in Bloomingdale

4.92 out of 5 average rating, 60 reviews

Family-Friendly Suburban Getaway Near Chicago

Home in Schaumburg

4.95 out of 5 average rating, 38 reviews

Unique 3BR Escape/ Pool, Vintage Decor & Big Yard

A tranquil backyard setting features a swimming pool reflecting soft lights from strings above. Lounge chairs are positioned around the pool, with lush greenery providing privacy in the background. The evening sky casts a serene ambiance over the outdoor space.

Home in Plainfield

4.94 out of 5 average rating, 85 reviews

Beautiful Spanish style Home (w/inground pool)

Top guest favorite

A fenced-in backyard features a landscaped yard with well-maintained grass surrounding a heated in-ground pool. The pool area includes a comfortable covered patio, providing shade with ample space for relaxation. Lush green trees and shrubs create a serene atmosphere.

Home in Crystal Lake

5 out of 5 average rating, 18 reviews

In Ground Pool, Full Ranch Home

Weekly house rentals

The exterior of a modern two-story bungalow is showcased, featuring gray siding and stone accents. A staircase leads to the front entrance, bordered by planters with greenery. Decorative lighting elements are mounted on either side of the entryway, adding to the home's architectural appeal.

4.96 out of 5 average rating, 23 reviews

The Architectural Haven

A cozy living room features a pair of dark blue sofas and a coffee table centrally positioned on a patterned area rug. Natural light enters through a window with sheer curtains, while a potted plant adds a touch of greenery. Dark curtains frame the window.

Home in Brookfield

4.88 out of 5 average rating, 58 reviews

Boutique Charmer Brookfield/La Grange

A spacious lakefront home is depicted, featuring a well-maintained garden with a variety of plants and natural pathways. The structure includes large windows and a covered patio area, surrounded by lush greenery and trees, providing an inviting outdoor environment.

Home in Downers Grove

4.94 out of 5 average rating, 47 reviews

Lakefront View Getaway Home! Hot tub! Kayak!

Home in Brookfield

4.88 out of 5 average rating, 42 reviews

Bliss in Brookfield- 5BR, 3BA

A multi-level living space is characterized by a sleek staircase with wooden steps and a glass railing. A modern entertainment unit and decorative shelving are positioned against the wall, creating an open ambiance. Natural light filters through large, partially covered windows.

4.94 out of 5 average rating, 69 reviews

Culinary DREAM - Pizza Oven/BBQ/Smoker

Top guest favorite

A modern dining area features a large marble table set with plates and utensils, surrounded by upholstered chairs. Pendant lights illuminate the space, highlighting the sleek kitchen in the background, equipped with stainless steel appliances and white cabinetry.

Home in Burbank

4.92 out of 5 average rating, 48 reviews

Cozy getaway in the city.

A dining area features a large wooden table surrounded by high-backed chairs, providing seating for eight. Sunlight filters through the window blinds, illuminating the bamboo flooring. In the background, a cozy living space with a gray couch is visible, enhancing the communal atmosphere.

4.78 out of 5 average rating, 9 reviews

2BDRM Entire Home+Pool Table- 20min to MDW

A spacious living area features a large sectional sofa, accented by scatter cushions. A coffee table is positioned on a light rug, with decorative items and plants arranged thoughtfully. Bright overhead lights illuminate the room, which includes a fireplace and large windows with soft window treatments.

Home in Willowbrook

4.92 out of 5 average rating, 24 reviews

Spacious and Inviting

Private house rentals

The exterior of the home is showcased, featuring a light-colored facade complemented by neatly trimmed shrubs. Stairs lead up to a welcoming entrance, while a well-kept lawn and mature trees provide shade. The roofline is distinctive, adding character to the overall appearance.

Home in Oak Park

4.93 out of 5 average rating, 29 reviews

Spacious Designer Oasis: Game Room - Yard - Garage

The living room features a cozy seating arrangement with two patterned armchairs and a light-colored sofa. A wooden coffee table sits atop a plush area rug in a neutral tone. Natural light filters through sheer curtains, illuminating the space.

Home in Burbank

4.85 out of 5 average rating, 93 reviews

Cheerful 2 Bedroom Home with parking on premise.

A well-lit dining area features a rectangular table accompanied by four wooden chairs and a bench. Natural light filters through large windows, illuminating the space. A small potted plant is centered on the table, enhancing the clean and modern decor.

Home in Westmont

4.88 out of 5 average rating, 16 reviews

Cute & Cozy Westmont, IL House Near the Best Areas

The bathroom features a sleek design with light grey tile flooring and patterned wall accents. A bathtub is partially obscured by a white shower curtain, and a dark vanity with a marble countertop is visible. Two bath mats provide comfort underfoot.

Home in Melrose Park

4.95 out of 5 average rating, 19 reviews

A ranch home within the outskirts of Chicago

Top guest favorite

Two inviting chairs with grey upholstery are positioned near a window, allowing natural light to brighten the space. A round black side table complements the chairs, adorned with a vase containing greenery and white flowers.

Home in Bridgeview

5 out of 5 average rating, 41 reviews

Lofty Urban Retreat

5 out of 5 average rating, 3 reviews

Lux Stay Sleeps 8: DT Geneva

Top guest favorite

The modern two-story house is surrounded by landscaped grounds, featuring a mix of wood and dark paneling. A spacious deck extends from the upper level, with seating and hanging planters. A pathway leads to the outdoor dining area, bordered by vibrant flower pots.

4.96 out of 5 average rating, 98 reviews

Steps from the beach and a mile from National Park

Top guest favorite

A modern kitchen features sleek dark cabinetry paired with light wood finishes. Stainless steel appliances include a refrigerator, oven, and microwave. A spacious countertop offers ample prep space, and a window allows for natural light to brighten the area.

Home in Schaumburg

5 out of 5 average rating, 56 reviews

Suburban Fab

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