House vacation rentals in Westchester

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Popular amenities for Westchester house rentals

House rentals with a pool

Top guest favorite
A spacious living room is highlighted by a stone fireplace, providing a cozy focal point. A gray sofa is positioned across from a glass coffee table, with a large area rug beneath. Light wood flooring is complemented by neutral-toned walls and soft gray curtains.
Home in Schererville
4.95 out of 5 average rating, 56 reviews

Cozy house in Schererville

AnyaRating, 5 stars2 weeks ago
Very well thought through place for every detail, with a mix of 70s wood style and some higher tech upgrades like the main bathroom mirror with light and anti fog, or sensor lights. Kate was very responsive and accommodating for the 1 baby & 1 toddler we asked for. The place was stocked with all necessary items especially in the kitchen with appliances and cutlery, coffee, tea. There were 2 hairdryers, nice shampoo and conditioner, shower gel.
Superhost
A sunny backyard features a round in-ground pool surrounded by lush green grass and vibrant flower pots. The house showcases a two-story design with a balcony and large windows, providing views of the serene outdoor space and nearby landscaping.
Home in Des Plaines
5 out of 5 average rating, 4 reviews

Rosemont 4BD2BA house with Pool

HannahRating, 5 stars1 month ago
Mike was very responsive leading up to our stay and very helpful whenever I had any questions about the property. The home was very clean and well maintained. Would recommend!
Guest favorite
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, 51 reviews

Now Open: Heated Pool with Entire House

TaraRating, 5 stars1 month ago
Moizs was an amazing host. Very accommodating, quick response, had some great recommendations for local restaurants, shopping, etc. Bloomingdale is a cute and nice suburb of Chicago. We had a great trip and we will definitely be back.
Top guest favorite
An outdoor space features a uniquely shaped pool surrounded by a spacious deck. Four lounge chairs and an umbrella are positioned near the water. Steps lead to a wooden deck above, while lush trees and greenery provide a natural backdrop.
Home in McHenry
5 out of 5 average rating, 20 reviews

Paradiso Vacation

ChrisRating, 5 stars1 week ago
Everything looked exactly like the pictures. So much to do at the house that we wished we would have stayed an extra day or two. Lots of space for our group of 7.
Guest favorite
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
4.93 out of 5 average rating, 27 reviews

Schaumburg Oasis:Private Pool & Enchanted Garden

TeddyRating, 5 stars6 days ago
They were a fantastic host, very responsive to every question and anything we needed. The location is quiet and amazing, great place to relax and enjoy time. love the pool! Will definitely stay again. 100% recommend!
Guest favorite
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, 77 reviews

Beautiful Spanish style Home (w/inground pool)

BethanyRating, 5 stars1 month ago
Stayed here the night before my wedding with my siblings who stayed the night of the wedding. We hosted our getting ready portion here for the morning of the wedding and Olinka and Daniel were gracious enough to allow us to stay in their beautiful home. Made for gorgeous pictures and a comfortable stay both nights. Thank you!!
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, 7 reviews

In Ground Pool, Full Ranch Home

ErinRating, 5 stars2 days ago
My friend and I booked with Patrick because it was an easy place to find in between where we live. It was also important that it was pet friendly because I had my 2 dachshunds and she had her German shepherd mix with a toddler. Kiddo enjoyed the pool, and the doggos loved the yard. We all felt at home!
Guest favorite
A serene pool area features a heated in-ground pool surrounded by lush greenery. Lounge chairs with red umbrellas provide shaded seating. Colorful flowers and tropical plants enhance the peaceful outdoor setting, creating an inviting place for relaxation.
Home in Miller
4.93 out of 5 average rating, 137 reviews

Bayless Dune Lodge at West Beach - Indiana Dunes!

KevinRating, 5 stars2 months ago
We had a great weekend getaway from Chicago and it was less than an hour (without traffic) away! Peaceful, quiet, near the beach. Cullen was an awesome host!

Weekly house rentals

Guest favorite
A spacious living area features two gray sofas and an ottoman, arranged on a light-colored rug. Large windows offer views of the river and allow natural light to fill the space. A dining table is situated nearby, enhancing the inviting layout.
Home in Elgin
4.9 out of 5 average rating, 78 reviews

Little house on the river

AnneRating, 5 stars1 week ago
Beautiful view! The house was cute and clean and very comfortable. The pictures don’t do it justice! Also, the Fox River Trail is right out the back door. It’s great for walking, biking or running along the river.
Guest favorite
A spacious living area features a comfortable brown sofa, accented by light-colored pillows. A decorative coffee table sits in front, and a dining space is visible in the background, furnished with white chairs surrounding a light wood table. Natural light brightens the room.
Home in Manteno
4.96 out of 5 average rating, 262 reviews

King-size beds ! All the luxeries of home!

ColeRating, 5 stars1 week ago
This property is great -- nice quiet neighborhood close to town. It is a comfortable home that looks brand new. Ami is a great host. Very responsive and easy to communicate with. I had a medical issue come up during my short stay and was able to easily and quickly extend my stay. Everything about my stay in this Airbnb was more than perfect and I highly recommend it to anyone looking for a place to stay here.
Top guest favorite
A game room features a felt-covered pool table, foosball table, and air hockey table against a backdrop of a beach scene mural. Orange-painted walls enhance the lively atmosphere. Several gray chairs are arranged neatly along one side of the room, providing ample seating.
Home in Elmhurst
5 out of 5 average rating, 57 reviews

Big Family Home, 4King Beds, Sleep22, Safe area

CedricRating, 5 stars3 days ago
I would definitely use this home again. The host, Syed, is very easy to communicate with and is quick to respond to any questions you may have. The place was cozy and relaxing for everyone. The basement was a hit with all the games and the beds are so very comfortable. The rooms do appear larger on the pictures, however, the place was well able to accommodate all of the guest. (18 people) Concerns would be to have enough bath/face towels for everyone especially if you are staying a few days. There is a laundry room though with a wonderful washer and dryer! Also, be prepared for ants. Maybe because of the season! Overall, I enjoyed my time there and would recommend it to others.
Superhost
An inviting living space features warm wooden ceilings and a polished table set for dining. Comfortable seating options are arranged around a media area with a television in view. Large windows allow natural light to brighten the room, enhancing the cozy atmosphere.
Home in Melrose Park
4.92 out of 5 average rating, 12 reviews

A ranch home within the outskirts of Chicago

Seung IlRating, 5 stars1 month ago
Juan was very kind and responsive on requests. Place was big enough to relax and comfortable stay
Guest favorite
A comfortable living area features two brown leather sofas, a coffee table, and a large television displaying a city skyline. Light hardwood flooring complements the soft blue walls. The space is well-lit, with a large window and a small area rug adding a cozy touch.
Home in Elmhurst
5 out of 5 average rating, 6 reviews

27min2City-Fun~SLP10-15~Large patio w/dining~BBQ

CoriantaRating, 5 stars1 week ago
The stay was great. My kids absolutely loved the ample space and the proximity to downtown Chicago.
Guest favorite
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
4.93 out of 5 average rating, 28 reviews

Bliss in Brookfield- 5BR, 3BA

TaiquitiaRating, 5 stars2 months ago
My stay was wonderful everything was nice. Communication was outstanding.
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
4.83 out of 5 average rating, 23 reviews

Cozy getaway in the city.

CynthiaRating, 5 stars1 week ago
Juan was not only a great communicator but his home was beautiful and centrally located. If ever in the Chicago/Burbank area would definitely love to rent.
Guest favorite
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.
Home in Lisle
4.97 out of 5 average rating, 36 reviews

Cute & Cozy Lisle, IL House Near the Best Areas

CarrieRating, 5 stars2 weeks ago
Was clean and with in distance of everything we had planned , easy to find, quiet location and responsive hosts

Private house rentals

Superhost
The exterior of a multi-story brick home is presented, featuring a distinctive rounded entrance. The facade showcases elegant architectural details and decorative trim, while landscaped greenery surrounds the property. A pathway leads to the front door, flanked by well-maintained shrubs and seasonal foliage.
Home in Berwyn
4.91 out of 5 average rating, 33 reviews

European Custom Built Home

EmilyRating, 5 stars2 months ago
House is vast, clean, and absolutely beautiful inside and out. Easy to get with a car or local transit and a short walk. Pictures don't do the house justice it has lovely historical features and more room than it seems between the three floors (ground floor, basement and upstairs). With two usable balconies and a patio backyard there is more enough space to entertain a small group outside.
Guest favorite
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 Austin
4.93 out of 5 average rating, 15 reviews

Spacious Designer Oasis: Game Room - Yard - Garage

Danielle GRating, 5 stars2 days ago
Rameez was an amazing host! Making the experience even more enjoyable with his quick responses & fast accommodations. The home is more spacious than it looks in the photos and it truly exceeded my expectations. I had a great stay for my birthday!
Superhost
A spacious living area features modern furniture, including a light-colored sofa, a dark armchair, and a wooden coffee table. A large area rug anchors the seating arrangement, while natural light enters through sliding glass doors leading to a deck. Decorative shelving adds visual interest to the walls.
Home in Elmhurst
4.79 out of 5 average rating, 29 reviews

Enamored in Elmhurst

JessicaRating, 5 stars1 week ago
Great place, clean house, beautiful neighborhood. Mark was very accommodating and easy to communicate with. Highly recommend this place as a stay!
Superhost
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, 56 reviews

Boutique Charmer Brookfield/La Grange

VesnaRating, 5 stars1 month ago
This house was on perfect location for us. Easy to walk to La Grange stores and restaurants, and also easy walk to Skadarliya where we attended an event. Quiet neighborhood with sidewalks. Nice fenced backyard. Weather wasn’t the best during our stay but backyard was protected from wind so we were able to spend a little time there. Our host was easy to reach couple times we needed her. Nothing big, just the app that should unlock doors was misbehaving for me, but once reinstalled it was so easy to use and easy to lock and unlock the door. Hair dryer died and Jolean delivered new one in few minutes. House had everything we needed. We will stay here again.
Guest favorite
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
4.97 out of 5 average rating, 38 reviews

Lakefront View Getaway Home! Hot tub! Kayak!

AnnaRating, 5 stars6 days ago
Hugo was a great host. The house was just like the listing, ideal for a weekend with friends. We were five couples with children, an ideal family atmosphere. It has games and equipment to enjoy the lake and garden, such as a small pool, life jackets, sport balls... It was a great weekend thanks to the space and the house, highly recommended!
Top guest favorite
The exterior of a charming Victorian home is showcased, featuring a spacious front porch with seating arrangements. Lush greenery lines the walkway, and decorative lights adorn the eaves. The entrance is marked by a welcoming front door, enhancing the inviting atmosphere of this historic property.
Home in Oak Park
4.98 out of 5 average rating, 96 reviews

Modern Victorian Charm | A+ Location in OP

SamRating, 5 stars1 week ago
Great place to stay while visiting family! Very kid friendly and baby items provided too! Loved this home away from home!
Guest favorite
A modern living room features a wooden coffee table central to a comfortable seating arrangement, including two sofas adorned with soft, textured pillows. Natural light enters through large windows, highlighting a textured wall art piece above the sofas and the warm wooden flooring.
Home in Gurnee
5 out of 5 average rating, 7 reviews

Luxury Stay Near Six Flags & Navy Graduation

ZylfijeRating, 5 stars1 week ago
We had a fantastic stay! James was extremely attentive and accommodating, communication was seamless from start to finish. The location was ideal for our family, just minutes from Six Flags, which made our trip so convenient. The house itself was incredibly spacious, giving everyone room to relax without feeling crowded. We especially appreciated waking up to the peaceful sound of birds chirping each morning, such a nice touch of nature. Every living area had its own TV, which made downtime easy for everyone, and the ping pong table added a fun extra activity for the family. The home was spotless upon arrival, very clean and well kept. You can tell the host takes pride in maintaining the property. Highly recommend staying here if you're visiting the area!
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
4.99 out of 5 average rating, 79 reviews

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

ZaffRating, 5 stars2 weeks ago
Such a BEAUTIFUL home ! The place is amazing and very clean. We really enjoyed our stay, the backyard is huge to let dogs walk around. The neighborhood is quiet and really nice ! Paul is very responsive and friendly! 10 out of 10 !

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