House holiday rentals in Oswego

4.92 out of 5 average rating, 118 reviews

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

LakeHome Cozy Retreat! HotTub• •FirePit•Bar & Fish

Come enjoy our beautiful home it's the perfect place to relax, unwind & enjoy peaceful lake views. Whether you’re fishing, soaking in the hot tub or sipping coffee on the deck, it’s a quiet home away from home on a serene cul-de-sac. Enjoy stunning views of the lake while grilling or relaxing by the firepit on the beautifully landscaped patio & in the hot tub 🥂 🐶 Up to 2 furry babies are welcome & they’ll love the almost 1-acre fenced yard! 🌅 See weekly & monthly discounts for longer stays

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, 179 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.

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.

4.87 out of 5 average rating, 149 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!

4.87 out of 5 average rating, 157 reviews

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

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.

4.96 out of 5 average rating, 157 reviews

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

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"! *Note: Pricing is based on "Double Occupancy". Extra charges per person apply after 2 guests. Can accommodate up to 6 guests. 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"!

4.95 out of 5 average rating, 130 reviews

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.

Home in Geneva

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.

4.97 out of 5 average rating, 269 reviews

Home in South Elgin

"Let it Snow Lodge", Red River Cottage w/firepit

December is filling up fast! 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.

4.9 out of 5 average rating, 140 reviews

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.

Home in Oswego

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.

4.91 out of 5 average rating, 121 reviews

The living area features a large sectional sofa with decorative pillows, positioned opposite a television mounted on a dark wood unit. Artwork depicting colorful pixel characters adorns the wall. An archway leads to a game room with a pool table and ambient lighting.

Home in Downers Grove

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!

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.

4.85 out of 5 average rating, 155 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, 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.)!

A spacious living area features a large, comfortable sectional couch accompanied by a round coffee table. Natural light enters through tall windows, highlighting the neutral walls and soft area rug. A modern television is positioned on a wooden media console, creating a cozy entertainment space.

4.92 out of 5 average rating, 112 reviews

4 Bedroom House - Close to Everything - Naperville

Enjoy all Naperville has to offer with this spacious 4 bedroom 2.5 bathroom home. Minutes from shopping, dining, and entertainment, this home is situated in a quiet and cozy neighborhood just a 10 minute drive to Downtown Naperville. Fully stocked kitchen and bathrooms, comfortable beds, fast wifi, Smart TVs, 2 car garage, spacious fenced back yard - everything you need to feel right at home!

4.93 out of 5 average rating, 117 reviews

A warm bedroom features a spacious bed adorned with a colorful quilt showcasing a star pattern. Two throw pillows with moose designs rest at the head of the bed. Wooden walls and rustic decor enhance the cozy cabin feel.

Home in Geneva

New Modern Log Home Retreat in the Heart of Geneva

Located minutes from bustling downtown Geneva, this authentic log home is nestled on a quiet residential street on a nature filled half acre. Built in 2007, this home will be yours to use as a homebase for downtime or as you explore the many sights, eateries, and shopping of Geneva and the surrounding area.

Popular amenities for house rentals in Oswego

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 19 reviews

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 bdrm 7 bed 2.5 bth Ranch w Fenced Yard Sleeps 10

Home in Bartlett

5 out of 5 average rating, 3 reviews

Elegant Executive Residence, Hot Tub & Pool

4.85 out of 5 average rating, 27 reviews

A spacious living area is characterized by a plush gray sofa and a round coffee table. Decorative wall elements and a vibrant red holiday tree enhance the modern decor. Soft lighting is provided by a statement chandelier hanging from the ceiling.

Home in Glen Ellyn

Pardizes Suites

4.76 out of 5 average rating, 51 reviews

The bedroom features a spacious bed adorned with soft linens and decorative pillows. Large windows allow natural light to fill the room, complemented by elegant sheer curtains. A distinctive floral accent wall adds character, and a bedside lamp provides warm illumination.

Home in Plainfield

30 mins to CHI, 3 Kings, BBQ Grill, TV, Spacious

4.95 out of 5 average rating, 42 reviews

Home in Schaumburg

Friends-Inspired Vintage Vibes House near Chicago

5 out of 5 average rating, 10 reviews

A spacious living area features a light-coloured sofa set positioned around a wooden coffee table, with a television mounted on the wall. A large area rug enhances the space, while plants and natural light provide a fresh atmosphere. Dining space is visible in the background.

Home in Schaumburg

Paradise with Pool & Games

4.91 out of 5 average rating, 11 reviews

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

Cloud 9: 4BR, Fully Fenced, 2 Story

5 out of 5 average rating, 9 reviews

Home in Elmhurst

Elmhurst 4BR Home with Pool | Mid-Term Ready

Weekly house rentals

4.94 out of 5 average rating, 16 reviews

The kitchen area features modern appliances including a refrigerator, microwave, and sink. Soft lighting illuminates the stone backsplash, enhancing the cream-colored cabinetry. A small seating area is present, accompanied by decorative elements such as potted plants and a mirror, contributing to a functional yet inviting space.

Home in Villa Park

Tranquil Hideaway

4.96 out of 5 average rating, 26 reviews

The cottage exterior features a welcoming porch with seating and decorative elements. A well-maintained pathway leads to the entrance, bordered by lush green grass and shrubbery. A vibrant American flag stands proudly in the front yard, emphasizing a sense of community.

Home in Saint Charles

The Crumb Cottage

5 out of 5 average rating, 98 reviews

Home in Geneva

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

A two-story home showcases a blue-gray exterior with a welcoming front porch and decorative door wreath. The structure is surrounded by mature trees, and a well-maintained front yard leads to a slightly elevated entrance. Upper story windows provide natural light to the interiors.

4.83 out of 5 average rating, 70 reviews

Little house on Prairie. Nautical theme 3 bedroom.

5 out of 5 average rating, 13 reviews

A serene creek flows through a lush green landscape, surrounded by trees with budding leaves. In the background, a house is partially visible amid the foliage, creating a peaceful natural setting.

Home in Plano

Little Rock Woods Retreat

4.85 out of 5 average rating, 54 reviews

A cozy bedroom features a spacious bed dressed in floral bedding, complemented by pastel pillows. Two nightstands frame the bed, and a light-colored rug covers the floor, adding warmth to the neutral walls. Soft lighting is provided by recessed ceiling fixtures, enhancing the serene ambiance.

Home in Woodridge

Cozy 1-Bedroom Apartment on the Ground Floor

A two-story house is showcased with a welcoming red front door framed by elegant columns. Large windows allow natural light to enter, while a well-kept lawn with scattered leaves enhances the outdoor space. A driveway leads to the attached garage, contributing to the home's practical charm.

4.82 out of 5 average rating, 38 reviews

Naperville Nest!

4.9 out of 5 average rating, 42 reviews

A wooden deck furnishes an outdoor dining area with a large table and chairs, set against a backdrop of lush greenery and expansive views of the river. The tranquil water glistens in the sunlight, bordered by trees that enhance the natural setting.

Home in Plano

Retreat on Fox River w/ Stunning Views & Hot Tub!

Private house rentals

4.92 out of 5 average rating, 25 reviews

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

Cute & Cozy Westmont, IL House Near the Best Areas

The exterior of a two-story house is shown, covered in fresh snow. The front features a clean façade with dark and light siding. Snow-laden shrubs frame the entrance, which is highlighted by a small porch. A garage door is visible to the right.

4.84 out of 5 average rating, 70 reviews

Cozy Home 3BD 2 BA: Central; I-88/Outlet Mall/Park

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.

4.88 out of 5 average rating, 50 reviews

Spacious family friendly home away from home

A cozy living room scene features a spacious sectional sofa adorned with patterned throw pillows. A tufted ottoman is positioned nearby, complemented by a small side table. Large windows allow natural light to fill the space, enhanced by light curtains and a decorative hanging plant.

5 out of 5 average rating, 8 reviews

Feathers Home, Cozy, King Bed

4.95 out of 5 average rating, 57 reviews

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

Beautiful Home

4.99 out of 5 average rating, 83 reviews

The kitchen features modern white cabinetry and stainless steel appliances, complemented by a spacious island with a decorative tray. Natural light floods the area through the nearby window, and a stylish backsplash adds an elegant touch to the space.

Home in Batavia

Bliss in Batavia near the Fox River

4.95 out of 5 average rating, 22 reviews

Home in Melrose Park

A ranch home within the outskirts of Chicago

The living room is spacious and features casual seating on a gray sectional sofa. Natural light enters through large windows, illuminating the polished floor. A round coffee table sits at the center, while a decorative bookshelf displays items against the wall. A ceiling fan enhances airflow.