We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

House vacation rentals in Westchester

Find and book unique houses on Airbnb

Top-rated house rentals in Westchester

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

0 of 0 items showing

1 of 3 pages

Top guest favorite

The living area features a cozy sofa and a patterned armchair, complemented by a glass coffee table. A television is positioned in one corner. Large windows invite natural light, while floor-to-ceiling curtains offer privacy. A potted plant adds a touch of greenery.

Home in Wilmette

4.98 out of 5 average rating, 171 reviews

Unique porcelain-enamel paneled "Lustron" home

This rare modern post war home has a style all its own. Created by Carl Strandlund in Columbus Ohio, it consisted of prefabricated porcelain enamel covered panels inside and out making it durable and easy to clean. Easing the postwar housing shortage and its maintenance free design were its selling points. Great care has been taken to reflect its true character so enjoy the well thought out floor plan and huge yard. Close to Northwestern, Gilson park beach, and downtown Chicago via car or train.

A dining area is presented with a long glass table set for six, surrounded by tall upholstered chairs. The space features a decorative rug beneath the table and wall art made of natural materials, with soft lighting illuminating the room.

Home in Elmhurst

4.85 out of 5 average rating, 110 reviews

Luxe 3BR, 2BA + Hot Tub

Discover our delightful raised ranch offering 3BR, 2 Full BA, and an updated kitchen. The open living and dining area is bathed in natural light, while the cozy family room awaits for relaxation. Attached garage. Relax in the sprawling backyard with upper and lower decks, a great hot tub. Easy access to I-294 and I-88, close to Elmhurst Hospital, 20 mins to chi. Indulge in snacks and coffee from the kitchen's bar for a perfect stay. Book now and cherish memorable moments in this tranquil haven!

A cozy living room features a brick fireplace as a focal point, surrounded by comfortable leather seating arranged for relaxation. Light-colored curtains frame large windows, while a plush area rug adds warmth to the wooden floor. A wooden door and wall decor complement the inviting space.

Home in Glen Ellyn

4.91 out of 5 average rating, 163 reviews

Home in Glen Ellyn

Beautiful 5 bedroom, 2.5 bath home in Glen Ellyn, fully furnished with everything you may need for a wonderful stay! Located in the peaceful suburbs of Glen Ellyn, the area is perfect for families or friends who would like a comfortable getaway. Located 40 minutes from downtown Chicago and Midway airport and 30 minutes from O'Hare airport. Located nearby major highways and shopping centers. Large, private and completely enclosed backyard perfect for kids to play in or a relaxed evening of BBQ!

Top guest favorite

A cozy living room features a gray sofa with decorative pillows, a round dining table with chairs, and a stone fireplace. Natural light enters through windows adorned with decorative molding, while a few bookshelves provide a space for books and decor. A colorful area rug adds warmth to the hardwood floor.

Home in Oak Park

4.98 out of 5 average rating, 175 reviews

Cozy, Clean, 4 Person, 1st Flr, w/Kitchen, Parking

Enjoy our historic district three-flat w/ free parking in upscale, safe Oak Park just 3 blocks to the train, easy access to Chicago. Enjoy some tranquil time in our little eco suburban farm. Check out the gardens and visit our 6 friendly chickens. This non-smoking unit with full kitchen is perfect for tourists, families, or business travelers. We require no check-out chores. Easy highway and airport access. No parties. Booking age, 25 or at least one 5 ⭐️ review. Visit profile for more units.

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, 160 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, 134 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!

Top guest favorite

A spacious living area features a cozy gray sofa adorned with colorful cushions, complemented by two vibrant blue chairs. A wooden coffee table rests on a floral area rug, while a flat-screen TV is mounted on the wall above a modern fireplace. Natural light enters through large windows.

Home in Schaumburg

4.96 out of 5 average rating, 98 reviews

Modern & Clean 3 Bedroom Ranch House with Sunroom

Kick back and relax in this fully renovated and stylish space. House is stocked with new kitchenware, appliances, smart TVs. This rental has everything you need! 6 miles to Schaumburg Convention Center, 17 miles to O'Hare Airport, 5 miles to Woodfield Mall. Enjoy restaurants, parks, golf courses, Legoland, Medieval Times and much more. This is a 3 bedroom 1 bathroom house with a beautiful sunroom that sleeps up to 6 people (2 in each bedroom). Garage is not available for guests' use.

Top guest favorite

The collage showcases various areas of the property, including a modern living space with a wall-mounted TV, a two-story exterior featuring stone details, an outdoor patio area with seating under a pergola, a game room equipped with a ping pong table, and a bathroom with a jacuzzi tub and neatly arranged towels.

Home in Westchester

4.97 out of 5 average rating, 110 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!

A modern kitchen features an island with seating for two and stainless steel appliances. White cabinetry contrasts with a dark backsplash, while large windows allow natural light to illuminate the workspace. The clean design promotes a functional and inviting cooking area.

Home in Elmhurst

4.96 out of 5 average rating, 125 reviews

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.

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)

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

4.91 out of 5 average rating, 114 reviews

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!

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, 112 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.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations with great services and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Westchester house rentals

Free parking on premises

Air conditioning

House rentals with a pool

A spacious living room features light hardwood floors and large windows that allow natural light to fill the area. Comfortable seating arrangements are provided with two armchairs, a sofa, and end tables. A flat-screen television is mounted on the wall, complemented by decorative wall art.

Home in Schererville

4.93 out of 5 average rating, 67 reviews

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

A bright living room features large windows offering city views and ample natural light. The space includes a comfortable sofa, unique upholstered chairs in green, and a modern coffee table. A flat-screen TV is mounted on the wall, complemented by a stylish floor lamp.

Home in West Loop

4.65 out of 5 average rating, 17 reviews

2BR w/ Stunning Views and Resort-Style Amenities

An aerial view showcases the impressive ranch home and its expansive grounds. The inground heated pool is bordered by lounge chairs, while a stone firepit is visible nearby. Lush green fields stretch beyond classic white fences, presenting a serene rural landscape.

Home in McHenry

4.88 out of 5 average rating, 88 reviews

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

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

4.7 out of 5 average rating, 27 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

An expansive indoor pool area is showcased, featuring a spacious heated sport pool and a circular hot tub. Large windows provide natural light and views of the outdoors, while decorative plants add a touch of greenery. A large TV is mounted nearby, enhancing the area’s entertainment options.

Home in McHenry

4.88 out of 5 average rating, 121 reviews

Highwood Haven/Indoor Pool/Hot Tub/Arcade

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

4.94 out of 5 average rating, 36 reviews

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

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

Large Spanish style Home (w/inground pool)

Weekly house rentals

Top guest favorite

A spacious living area features a large sectional sofa arranged around a circular coffee table. A television is positioned on a media stand, and natural light enhances the room through a large arched window, complemented by decorative plants and neutral-colored accents.

Home in Elmhurst

4.95 out of 5 average rating, 40 reviews

Premier 5BR/3BA Modern Retreat with King Suite!

A spacious dining area is highlighted by a large wooden table surrounded by light-colored upholstered chairs. The walls are painted a calming blue, complemented by large windows that allow natural light to fill the room. Elegant curtains frame the windows, adding a touch of softness.

Home in Brookfield

4.9 out of 5 average rating, 39 reviews

Bliss in Brookfield- 5BR, 3BA

The outdoor patio area is illuminated by string lights, creating a warm ambiance. Patio furniture, including a dining table and several chairs, is arranged for relaxation and dining. A grill is placed nearby, surrounded by a grassy area and a tall tree in the backdrop.

Home in Elmhurst

4.98 out of 5 average rating, 64 reviews

King Bed - Entire Home - Private corner lot

Top guest favorite

A remodeled kitchen features a large island with three wooden stools and a copper accent. A vintage red refrigerator stands against a backdrop of grey cabinets and an exposed wooden beam ceiling. Open shelves showcase kitchenware alongside rustic decor elements.

Home in Oak Park

5 out of 5 average rating, 51 reviews

Oak Park - Wine House!

An open floor plan showcases a spiral staircase made of warm wood, leading to the second floor. Natural light fills the space, highlighting polished wooden floors and a cozy living area to the left, where a light gray couch is positioned.

Home in Wood Dale

4.93 out of 5 average rating, 15 reviews

Serene Home Privately Nestled on 1.5ac of Forest!

A spacious living area is presented with a large teal sectional sofa, accented by orange chairs. A round, metallic coffee table sits atop a striped rug. The open layout leads into a modern kitchen, visible in the background, with bright lighting and stylish decor.

Home in Oakbrook Terrace

4.72 out of 5 average rating, 68 reviews

Desirable chic home in a Prime Location!

The exterior of the Retro Cottage is showcased, featuring a private front yard with a stone pathway and lush greenery. A blue door is framed by a trellis, and the cottage's charming facade is complemented by surrounding trees and plants. A gentle sunset sky adds warmth to the scene.

Home in Oak Park

4.84 out of 5 average rating, 38 reviews

Charming Retro 2BR Cottage/Train/Laundry/FREE PKG

A comfortable living area features a light gray sofa positioned next to a white entertainment unit. A flat-screen TV is mounted on the wall, and a large area rug with intricate patterns covers the hardwood floor. Natural light from the windows brightens the space.

4.96 out of 5 average rating, 49 reviews

Cute & Cozy Lisle, IL House Near the Best Areas

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.

4.92 out of 5 average rating, 25 reviews

Spacious Designer Oasis: Game Room - Yard - Garage

Top guest favorite

An open-concept living area features a spacious layout with cozy sectional seating and a light area rug. A dining table is visible in the background, complemented by modern pendant lighting. The kitchen boasts a large island with bar stools and stainless steel appliances, with natural light streaming in through large windows.

Home in Homewood

5 out of 5 average rating, 13 reviews

Modern Charming Home w/Pergola & games

A cozy living area features a mix of seating options, including a dark sofa and a light brown couch adorned with colorful pillows. A wooden coffee table sits center stage on a patterned rug, while natural light filters through the sheer curtains of a large window.

Home in Streamwood

4.95 out of 5 average rating, 57 reviews

Cozy Retreat in a Prime location

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, 49 reviews

Beautiful Home

A spacious living area is highlighted by a mix of modern and classic furnishings, including a light-colored sectional and a leather sofa. Sunlight enters through large windows, illuminating a central coffee table atop a textured area rug. Decorative accents and plants enhance the room's inviting feel.

Home in Villa Park

4.93 out of 5 average rating, 15 reviews

Family Friendly Stylish Villa Park Home!

A comfortable living room features a dark gray couch with decorative pillows and a patterned armchair. A wooden coffee table sits next to a lamp providing soft lighting. Artwork with floral designs adds a pop of color on the wall, while a potted plant enhances the space.

Home in Franklin Park

4.85 out of 5 average rating, 33 reviews

Guest Favorite Spacious Home Near Chicago O'Hare

An open-concept kitchen is visible, featuring modern cabinetry and a spacious countertop. A dining table with wooden chairs occupies the center, while a black refrigerator and oven are positioned along one wall. Natural light filters in through the window, complemented by contemporary light fixtures.

Home in Maywood

4.93 out of 5 average rating, 56 reviews

Fully Remodeled Large Home

A bright living area is filled with comfortable seating, including two armchairs and a spacious sofa. A light area rug with a geometric pattern covers the floor. Natural light streams in through large windows adorned with wooden blinds, and a decorative tray sits on a plush ottoman.

Home in Lombard

4.94 out of 5 average rating, 36 reviews

Spacious Home in Chicago Suburbs

Destinations to explore