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.

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Superhost

A modern living room features a large, curved green sectional sofa and a blue accent chair. A round, light-colored coffee table sits at the center, complemented by decorative items. Large windows provide natural light, while an artistic light fixture enhances the space.

Home in Lake View

4.87 out of 5 average rating, 127 reviews

Soak Up Mid-Century Style in Wrigleyville and Boystown

This is an architecturally significant (3-bedroom 3.5-bathroom) home by noted Las Vegas architect Homer Rissman. We are located in the heart of East Lakeview, just half a block from Lake Michigan and Lincoln Park, and blocks away from Wrigley Field and Boystown. Smart TVs (with Netflix, Hulu, Amazon Prime) are located in the shared main level TV lounge, and also the lower level lounge. Entire home I like in-person check-in but full privacy is offered You will receive a link with detailed instructions within 24 hours of your check-in. If you have a U.S. mobile number, you will also receive a text message FULL DISCLOSURE: If you haven't used a lockbox (or don't know how to), self-check-in isn't for you. Your check-in should be in person. Lakeview is home to two of the most vibrant sports, nightlife, and theater scenes in Chicago: Wrigleyville and Boystown. Explore souvenir shops and casual eateries by day, and hop from bar to bar along Clark, Addison, and Sheffield Avenues by night. You walk to Treasure Island (half block), Jewel Osco (2 minutes), Whole Foods (4 minutes), Lakeview Athletic Club (4 minutes), XSports Fitness (5 minutes), Walgreens (3 blocks), bars and restaurants aound the corner. Close to multiple buses on Lake Shore Drive. Grab a bus to downtown in 15 minutes You will have to climb one flight of stairs for all bedrooms Street parking is free on the east side of Broadway. The west side requires 383 permits. Please, read the signs.

Guest favorite

The image showcases a serene riverbank along the Fox River, with manicured green grass leading to the water's edge. Two decorative stone vases sit beside a paved area that meets the river, and trees line the opposite bank under a clear blue sky.

Home in South Elgin

4.92 out of 5 average rating, 250 reviews

Riverfront rental with fun activity

Riverfront Rental Sits on a quiet street in downtown South Elgin. This home gives you complete access to the Fox River. The bedrooms are on the main level, along with a beautiful kitchen featuring cherry cabinets and an island with breakfast bar, and an awesome four-season porch overlooking the backyard and the beautiful river setting. The second-level loft has great natural light . Outside, you'll find concrete patio and walkway, and stairs leading down to the river and firepit. no pets

Superhost

An outdoor space features a gazebo and comfortable seating, framed by vibrant flowers. The heated above-ground pool is visible, surrounded by a wooden deck. Lush greenery serves as a backdrop, creating a serene setting enhanced by soft evening light.

Home in Carol Stream

4.42 out of 5 average rating, 24 reviews

Amazing Summer Pool Awaits You!

Vacation, Staycation or Business, you will love your stay at this beautiful paradise with heated pool and tri-level entertainment deck equipped with grill and outside seating and gazebo! Semi-secluded backyard, walking distance to bike path, playground, skate park, walking trails, restaurants and even the gym! Relax on the magnificent deck while watching the sunset This home is pet free and smoke free. Pool is available May-Sept. WiFi is available throughout and Smart TV in the family room.

Top guest favorite

A small workspace with a wicker desk and chair is illuminated by a lamp, set against a light-colored wall adorned with nautical-themed decorations. The adjacent area features beige seating and a doorway leading to the living space.

Home in Cedar Lake

5 out of 5 average rating, 12 reviews

Charming Lake House with Private Lakeside Park

3BR/2BA lake house with private access to lakefront park with an amazing pier, picnic tables, benches on the lake, children's swings, sand, volleyball + more. This gated lake park is the best around! Feel the escape in our charming lake house adorned with lake-life decor. Relax on the woodsy front patio or back porch with lake view. Bonuses: We're on the same block as Bugaboo bar + grill and Bugaboo lake sport rentals. Just a 5-min drive to the iconic Lighthouse restaurant and town grounds.

Guest favorite

A dining area is showcased with a large wooden table surrounded by eight chairs. Wooden flooring reflects natural light from windows, while a unique pendant light hangs above. Nearby, an open layout leads into a kitchen, enhancing the spacious atmosphere.

Home in Chesterton

4.91 out of 5 average rating, 120 reviews

Downtown Chesterton "Grant-Cottage"

Charming downtown house with a front porch, back deck & covered patio. Beautifully decorated with a small fenced in backyard. Minutes from the Indiana Dunes National Park and beaches. Near the South Shore Commuter train if you wish to visit Chicago without the drive and expense of parking. We are across from an active train track so if you like trains you can watch them from the front porch. Walk to restaurants, wineries and beer pubs. European market on Saturdays from May to end of October.

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, 246 reviews

Small Red River House W/Firepit & Tire Swing!

Greetings Airbnb fans! Happy Spring! Here is 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.

Superhost

Home in Round Lake Beach

4.89 out of 5 average rating, 200 reviews

Corner Lakefront Property

This unique place has a style all its own. This corner lake house comes with a huge fenced-in yard, as well as a balcony off of the master bedroom and 2 parking spots. We offer 3 kayaks with life jackets, 1 paddle board, paddle boat and fishing poles, fire pit, outdoor and indoor games. We have 3 bedrooms with beds included, as well as a futon couch a trundle bed and a pull-out couch bed (6 potential beds total). This comes with 2 TVs, fireplace, WiFi, bar, new fridge and more.

Top guest favorite

A serene living area features a large sliding glass door leading to a deck with unobstructed views of Round Lake. Natural wood accents adorn the wall, while a plush sofa and a small coffee table create a relaxing seating space.

Home in Round Lake Beach

4.99 out of 5 average rating, 143 reviews

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!

Superhost

A private hot tub is situated under a wooden pergola, surrounded by privacy curtains. The bubbling water creates an inviting ambience, offering a relaxing space for unwinding outdoors throughout the year.

Home in Homewood

4.91 out of 5 average rating, 123 reviews

Peaceful & Private Hot Tub Vacation Home Getaway

A Rare gem 💎in the heart of Homewood. This Quaint 2-bedroom remodeled home is charming, sophisticated and discrete. It is minutes away from the Metra station, golf course and downtown Homewood shops. The energy is very calm and quiet ☯️. This is the home away from home where details are everything and the pictures do not capture the essence of this luxurious space. Experience the love, the joy and the peace that continues to leave its mark. Peace and Love - Michael and KP💞

Top guest favorite

A well-lit living room features a contemporary sectional sofa arranged around a central space. A large mirror reflects natural light, while a flat-screen television is mounted on the wall. Light-colored walls and warm wood flooring contribute to the open, welcoming ambiance.

Home in Addison

4.96 out of 5 average rating, 82 reviews

Home in Unincorporated Addison. RV & Pet Friendly

Your family will be close to everything when you stay at this centrally-located place. This house is extremely family friendly. It has 4 bedrooms and three baths. It has been recently remodeled inside and out. The yard is close to 3/4 acres and has a kids playground and firepit. The driveway is long and can park a long RV if needed. This is a quiet location. Fully Fenced in Yard with lights all around the house. Very safe location.

Superhost

Home in Ingleside

4.81 out of 5 average rating, 102 reviews

Lake house Monica Steps from the lake! 4BD 3bath

4BR/ 2.5Ba 3000ft2 Fun Lake house Monica at Duck Lake Lake front house, back your great for fire pit. Large Porch whit barbecue. Fire place, 75inch TV, internet, 4 great bedrooms additional bathroom in the basement, 2,5 bath, laundry room, games room: pool table, pingpong table, darts, soccer game, full kitchen, 6 parking space + 2 garage space, 2 bikes, 6 kayaks, private lot . Romantic and Family friendly.

Superhost

The exterior of a two-story vacation home is displayed, featuring a light grey facade with red trim around windows. A front porch is visible, complemented by wooden railings. Clear blue skies and scattered clouds form the backdrop.

Home in Cedar Lake

4.84 out of 5 average rating, 248 reviews

Vacation home on south end of Cedar Lake

Private two story fully furnished older vacation home on the south side of cedar lake. Both bedrooms and half bath are upstairs. Main level has living room/dining room combo, kitchen and full bath. Short drive to marinas with kayak/boat rentals, public beach and boat launches. Within walking distance is a bar/restaurant with kayak rental.

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What guests are saying

Enamored in Elmhurst

4.86 out of 5 average rating, 22 reviews1 month ago

This home is in a beautiful neighborhood. It was very clean and the decor was simple yet stunning. There was plenty of linen and the kitchen was stocked well enough to cook an entire meal Mark was very responsive and provided clear instructions for check in and out. I would stay here again

Home in Elmhurst

What guests are saying

The Waverly Retreat

4.87 out of 5 average rating, 39 reviews1 month ago

We stayed in Kayla’s house with our 2 small kids for 2 months, and we really felt like at home. She is an amazing host. She made sure that we were comfortable at all times, always offering her help and support. Before arriving, she recommended activities to do with the kids, and even bought some age appropriate toys. Upon arrivals eggs from her own chickens were waiting for us in the fridge. She called somebody to come over and clean our pathway from snow (without us asking) and even brought herself a sled for our oldest to enjoy the snow. We could not have asked for more, really 😊 The house is great, spacious, and cozy. We fell in love with the master bedroom and bathtub. And got to enjoy the garden and the patio during the sunny days. In summary, we could not have chosen better! Totally recommended

Home in Porter

What guests are saying

Heart of the Fox Riverhouse

4.98 out of 5 average rating, 40 reviews5 days ago

Not only was Meghan's place beautiful and scenic, but it had so many amenities to take advantage of. From boards games on stormy nights, to the hot tub and yard games during sunny mornings. This place had all the options. The house itself was just right for our group of 6 and was stocked full of kitchen equipment for meals, using the grill, making smores, and making coffee. By the end of the trip, all of my friends said they would love to come back to this place later in the year. Meghan herself, was very responsive and accomodating to any questions or needs that we had to make the weekend we stayed there a great one.

Home in McHenry

What guests are saying

Sanctuary on the Ravine

5 out of 5 average rating, 28 reviews8 months ago

The Woodland house is truly incredible, with every detail thoughtfully designed for comfort, from the cozy bedrooms and soft linens to the inviting beds. The kitchen nook with a couch overlooking the ravine offers stunning views of nature, making it a picturesque spot to relax. The home exudes warmth and is perfect for unwinding in the spacious sunken living room or one of the multiple outdoor seating areas. Debra was an excellent host, providing all the amenities you could need. This home is a 10+, and you won't want to leave!

Home in Highland Park