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House vacation rentals in Oswego

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Top-rated house rentals in Oswego

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

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A modern two-story house features a light, neutral exterior with decorative shutters. The inviting front yard is well-maintained, including colorful shrubs and a manicured lawn. A garage door is visible on the right side, and tall trees frame the property against a clear blue sky.

Home in Naperville

4.86 out of 5 average rating, 146 reviews

California King Bed | Fast Wi-Fi | 75" Smart TV

Our 3bd, 2.5ba house is perfect for a group of friends or family looking for a clean, modern place in a wonderful, quiet neighborhood. Built w/ cathedral ceilings, there is plenty of space for 10 people to sleep comfortably (6 beds & several comfy couches), as well as 3 smart TVs (w/ complimentary Hulu & Disney+), an indoor fireplace, a gas grill & large yard (including outdoor games), a desk space, & more. Enjoy close access to main roads & large stores (Costco, Walmart, hardware stores, etc.)!

Top guest favorite

A cozy bedroom features a comfortable bed with a quilted cover and decorative pillows. A colorful textile art piece depicting Route 66 is displayed on the wall. A side table with a lamp adds to the charm, complemented by a vintage photograph hanging above.

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 spacious master bedroom features a large bed with a neutral-coloured duvet, accompanied by decorative pillows. A ceiling fan provides ventilation, and natural light filters through sheer curtains. A cozy chair offers additional seating, with framed art adorning the walls.

4.9 out of 5 average rating, 173 reviews

Large Family Home w/Garage-King beds, Fast Wi-Fi

Relax and enjoy this open, well lit piece of suburbia designed and furnished to be the fully outfitted home away from home. Before every reservation this home is throughly cleaned and given ozone and UV treatment to sanitize. This home includes amenities like the fire pit and grill on the back porch, the 2 car garage, and a finished basement with a ping pong table and PlayStation. Particular favorites also include the fully outfitted kitchen, and the large master bedroom with a private bath.

Top guest favorite

A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.

4.98 out of 5 average rating, 161 reviews

Retro Modern Bungalow | free parking | fire pit

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

4.85 out of 5 average rating, 135 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!

A single-story ranch home is presented with a dark blue exterior and white shutters. A neatly trimmed lawn and concrete pathway lead to the front door. Flanking the entrance, small shrubs add greenery, while a tall evergreen tree stands nearby.

Home in Montgomery

4.86 out of 5 average rating, 148 reviews

Nice, Private Ranch Home

Nice private ranch home in a quiet neighborhood. Fox River and the river bike trail are only 3 minutes away, Rush Copley Medical Center, lots of shopping and dining options within minutes, Phillips park zoo, and water park very close, major roadways to Chicago. 10 min, from downtown Aurora where you can find the Hollywood Casino, Paramount theatre, many shopping stores and you can enjoy a walk along the Fox river, Fox valley mall and the Chicago premium outlets mall are only 20min away.

Top guest favorite

A bedroom features hand-painted floral murals on the walls, complemented by light-colored curtains framing a window. A spacious bed with white linens is centered on a patterned floor. A cozy sitting area with a dark wicker chair adds to the comfort of the space.

4.94 out of 5 average rating, 107 reviews

The Secret Garden

Summer is COOLER in Geneva! Located just 3 blocks from shops and restaurants in beautiful, downtown Geneva. Our space can sleep up to 4 comfortably. We offer amazing amenities like plush bed & linens, array of coffee and teas and goodies, 50" flat screen smart tv for watching movies after a day of fun in Geneva. Beautiful bath equipped with everything, including homemade salt scrub. A secure, separate entrance to come & go. It is a basement soace so ceilings are lower than average home.

The exterior of a red cottage is illuminated by warm outdoor lighting at dusk. A welcoming porch is highlighted, with two front windows reflecting a soft glow. Lush greenery and flowerbeds surround the property, contributing to a tranquil atmosphere.

Home in South Elgin

4.97 out of 5 average rating, 257 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.

A spacious living room features a large sectional sofa and two blue upholstered chairs, arranged around a black coffee table on a light area rug. A flat-screen TV is mounted on the wall, flanked by shelves with decorative items. Natural light enters through large windows with sheer curtains.

4.9 out of 5 average rating, 134 reviews

Cozy 4-bedroom ranch - minutes from everything

Relax and have fun with the whole family at this peaceful place to stay. It is located within walking distance from US Route 34 in the middle of shopping centers such as Meijer, Jewels, Target, Walmart, great restaurants, bars, entertainment, hair and nail salons, gas stations, etc. There are 5 beds (1 king and 4 queens plus a queen-size air mattress and a twin pull-out bed) and 3 couches waiting for their guests. The house is cleaned and sanitized before every reservation.

Top guest favorite

An upgraded patio features a hot tub illuminated in blue, with a scenic view of the lake and a vibrant sunset reflecting on the water. The outdoor dining area is nestled under string lights, adding a cozy touch to the serene atmosphere.

Home in Carol Stream

4.92 out of 5 average rating, 112 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)

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, 159 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.

Top guest favorite

A welcoming living room is highlighted by a comfortable sectional sofa with decorative pillows. A patterned area rug covers the hardwood floor, and a reading nook features a unique egg chair. Artwork adorns the walls, complemented by greenery from potted plants.

Home in Lombard

4.99 out of 5 average rating, 122 reviews

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!

Vacation rentals for every style

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Popular amenities for Oswego house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

A spacious living area is presented with a large, U-shaped sectional sofa and a matching armchair. A coffee table sits in the center, complemented by light hardwood floors and a patterned area rug. Natural light filters through a nearby dining space, featuring a table set for meals.

Home in Montgomery

5 out of 5 average rating, 13 reviews

5 bdrm/2.5 bth/Fenced Yard/Quiet St /Pet friendly

4.89 out of 5 average rating, 9 reviews

Harbor Inn - Canal Port

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

4.72 out of 5 average rating, 29 reviews

Spacious 3 Floor Townhome

A spacious basement game area features a classic pool table with a vibrant green felt surface, complemented by cues and an arranged set of colored balls. Nearby, a seating area with leather couches and an arcade machine is visible along the wooden-paneled wall.

Home in Bloomingdale

4.92 out of 5 average rating, 60 reviews

Now Open: Heated Pool with Entire House

A spacious backyard is illuminated by soft evening light, showcasing a lush green lawn framed by well-maintained gardens. Multiple seating areas are visible, including a hammock, lounge chairs, and patio furniture. A large tree offers shade, while a pool is partially seen beyond the greenery.

Home in Schaumburg

4.95 out of 5 average rating, 37 reviews

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

A welcoming entrance features a blue door with an anchor motif, flanked by two blue chairs. Sunlight streams across the porch area, which is shaded by the overhead lattice. Adjacent buildings are visible in the background, illustrating the inviting outdoor setting.

4.9 out of 5 average rating, 21 reviews

The Nautical Nest

A modern kitchen is showcased with sleek white cabinetry and stainless steel appliances. An island with bar seating is positioned in the foreground, while a spacious archway leads to an elegantly designed hallway featuring artwork and natural light.

Home in Plainfield

4.94 out of 5 average rating, 85 reviews

Beautiful Spanish style Home (w/inground pool)

The living room features a stone fireplace beneath a mounted television, with multiple windows allowing natural light to illuminate the space. A cozy sectional sofa is positioned on a textured area rug, complemented by a couple of side tables. Lush greenery from potted plants adds a refreshing touch.

Home in West Chicago

4.89 out of 5 average rating, 9 reviews

Cloud 9: 4BR, Fully Fenced, 2 Story

Weekly house rentals

Top guest favorite

A cozy living area features a deep-seated leather couch and a reclining chair, surrounded by bookshelves filled with antique books. A coffee table sits in front of the fireplace, which casts a warm glow. Large windows offer natural light, with a small dining table for four nearby.

5 out of 5 average rating, 24 reviews

The Gurler House

A well-lit bedroom features a spacious bed adorned with light gray bedding. A large mirror and a television are positioned against the wall, complemented by a lamp providing additional light. Soft curtains frame a window overlooking the outdoor area.

4.89 out of 5 average rating, 46 reviews

Spacious family friendly home away from home

Top guest favorite

A gathering area by the water features five comfortable chairs arranged around a rustic stone fire pit. The lush green lawn extends toward the river, with trees providing a backdrop against a sunset sky dotted with soft clouds.

Home in Wilmington

4.97 out of 5 average rating, 71 reviews

Waterfront dog friendly 3 bedroom home w/game room

Top guest favorite

An open living area features a spacious brown sofa paired with two armchairs. A round marble coffee table sits in front, while a dining table for four is positioned nearby. The kitchen is equipped with dark cabinetry and stainless steel appliances, with natural light illuminating the space.

Home in Romeoville

4.94 out of 5 average rating, 50 reviews

Beautiful Home

A wooden dock extends into the calm water, framed by lush greenery and trees. Two metal chairs sit on the dock, offering a serene spot to enjoy the lake views.

Home in Downers Grove

4.93 out of 5 average rating, 45 reviews

Lakefront View Getaway Home! Hot tub! Kayak!

Top guest favorite

A bright and open kitchen and dining area features a large island with seating and a dining table set for multiple guests. Modern appliances are visible in the background, along with stylish cabinetry. Natural light fills the space through large windows with sheer curtains.

5 out of 5 average rating, 92 reviews

OutdoorOasis-King bed-Fire Pit-Mins to town-EV cha

The exterior of a two-story home is shown, featuring a light yellow facade and white trim. A covered porch with steps is visible, framed by colorful autumn foliage. Well-maintained landscaping lines the walkway, enhancing the inviting appearance.

Home in Downtown Naperville

4.87 out of 5 average rating, 45 reviews

Quaint and Quiet - Downtown Naperville!

The image showcases a modern bedroom entrance, featuring a spacious bed adorned with decorative pillows and a soft blanket. A door leads to a bright bathroom equipped with a walk-in shower and elegant lighting. Neutral tones create a calming atmosphere in this inviting space.

Home in Saint Charles

5 out of 5 average rating, 20 reviews

Modern & Tranquil Stay: Hot Tub & Espresso Machine

Private house rentals

The spacious living area features light wood flooring and large windows allowing natural light to fill the room. A gray sofa with colorful cushions is placed centrally, flanked by two teal chairs. A modern coffee table sits in front, and a television is mounted on the wall.

5 out of 5 average rating, 19 reviews

Retro Home

A modern dining area is highlighted by a sleek table surrounded by six white chairs with gold accents. A contemporary light fixture hangs above, and the space features a stylish fireplace on the wall. Large glass doors offer access to the outside.

Home in Downers Grove

4.88 out of 5 average rating, 40 reviews

Luxury Bliss: Opulent 5BR/3.5BA Delightful Escape

The exterior view of Riverhouse Cottage is presented, featuring a charming blue facade and well-maintained landscaping. Lush green grass surrounds the home, and trees provide shade, with a sunset sky creating a serene backdrop.

Home in Saint Charles

4.9 out of 5 average rating, 52 reviews

Cozy Riverhouse Cottage - St. Charles

Top guest favorite

A modern living space features a sectional sofa adorned with a throw blanket, complemented by an accent pouf. A central area rug adds warmth to the room, which is well-lit by pendant lighting and natural light from the windows. The kitchen is visible in the background.

5 out of 5 average rating, 43 reviews

Perfect little paradise

A modern dining area features a glass table surrounded by six blue upholstered chairs with decorative detailing. Above, sleek chrome pendant lights provide illumination. A large window allows natural light to fill the space, complementing the blue wall and area rug beneath.

Home in Plainfield

4.81 out of 5 average rating, 42 reviews

Plainfield Home near Harrah’s Casino & Restaurants

A modern kitchen is highlighted by sleek white cabinetry and a polished countertop. A double sink with a contemporary faucet is centered, accompanied by a bamboo cutting board. Natural light enters through a window above the sink, providing a view of the outdoors.

5 out of 5 average rating, 3 reviews

Peaceful Cozy Corner Home

Top guest favorite

The spacious family room features a high vaulted ceiling with exposed wooden beams. A stone fireplace provides a central focal point, and a large TV is mounted above it. Comfortable seating is arranged for relaxation, complemented by a stylish area rug.

Home in Des Plaines

4.98 out of 5 average rating, 93 reviews

NEW~2 Spa Baths~Game Room~Prime Area~Big Yard~

A basement entertainment area is showcased, featuring a red felt pool table with balls arranged for play. Black bar stools are positioned along one side, and a wall-mounted TV displays a sports game. A refrigerator is visible in the background.

4.94 out of 5 average rating, 35 reviews

Ultimate Game House with Pool Table, Piano & More!

Quick stats about house rentals in Oswego

Total rentals
10 properties
Nightly prices starting at
R695 ZAR before taxes and fees
Total number of reviews
820 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi

Destinations to explore