House vacation rentals in Westchester

Find and book unique houses on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Westchester house rentals

House rentals with a pool

Guest favorite
An outdoor deck features a modest above-ground pool surrounded by wooden fencing. Two lounge chairs are placed on a textured rug, providing a relaxing seating area. Lush greenery is visible in the background, under a clear blue sky.
Home in Schererville
4.94 out of 5 average rating, 52 reviews

Cozy house in Schererville

CarlosRating, 5 stars1 week ago
Kate’s place was exactly what I expected. Pristine condition and spotless. Kate accommodated my early arrival which was greatly appreciated. I would 100% book this place again. Highly recommend her place to anyone in the area for a weekend or just to get away from the city. Thank you again for your attention on such a short notice on my booking.
Guest favorite
A spacious living room is featured with a cream-colored sectional couch facing a mounted flat-screen TV. Natural light pours in through large windows adorned with blinds. A stone accent wall adds texture, complemented by two decorative pieces and a ceiling fan.
Home in Munster
5 out of 5 average rating, 10 reviews

Munster hide away

ChristopherRating, 5 stars4 months ago
Nice house with updates. We used all four bedrooms, so everyone had their own space. Kitchen and living room looked nice, but a bit cozy if everyone was in the space at the same time. There was a large breakfast nook/counter in the kitchen instead of a table. More dishes, mugs, etc. in the kitchen would have been nice. The coffee maker and provided K-cups were great! Would definitely stay again if it's available when we are in the area again.
Guest favorite
A private heated pool is surrounded by a spacious wooden deck, furnished with lounge chairs and shaded umbrellas. A dining area with multiple tables sits nearby, covered by a clear blue sky and lush green trees, creating an inviting outdoor relaxation space.
Home in Chesterton
4.98 out of 5 average rating, 40 reviews

Pool House near the Indiana Dunes

KrishnaRating, 5 stars7 months ago
We had a great stay!! The house was perfect for the five of us and our dog, with enough space for all of us to feel comfortable. The bathrooms were clean and the kitchen was well stocked. The pool was the best part! Melissa was super prompt when it seemed like the heat to the pool wasn’t running and we were back in there in no time - the heated water was perfect for this fall weather! We also tried some of the recommended spots and overall, this was exactly the quick getaway we needed!
Top guest favorite
A clear swimming pool is surrounded by lush greenery and a wooden deck. Lounge chairs are placed nearby, and a colorful inflatable pool float rests on the water's surface. Sunlight reflects off the pool, enhancing its inviting blue color.
Home in Bloomingdale
4.94 out of 5 average rating, 48 reviews

Whole House With Hot Tub And Spacious Bedrooms

KarinaRating, 5 stars2 weeks ago
Amazing stay! This place has everything you need for both short and long visits. The location is extremely safe and convenient with shops within walking distance. My family and I thoroughly enjoyed the entire property, especially the game room and TV room which were perfect for entertainment. Moiz, the host, was very kind and quick to respond to any needs we had. Thank you for everything! We would definitely stay here again
Top guest favorite
A welcoming sitting area features original inlaid floors and large leaded glass windows, allowing natural light to fill the space. Traditional furniture includes a wooden loveseat and two accent chairs, with a round ottoman positioned centrally, enhancing the room's charm.
Home in Woodstock
4.88 out of 5 average rating, 60 reviews

Grand 1800s Victorian Gem: Updated/by Downtown

BeckyRating, 5 stars1 week ago
Deidre is an amazing host. She goes above and beyond for each guest. We always appreciate her welcoming us into her home and her attentive and responsiveness to our requests. Highly recommend!
Superhost
An above-ground pool is visible in the backyard, surrounded by greenery. Colorful floating loungers are placed in the water. A spacious deck with seating overlooks the pool area, while a grassy lawn provides additional space for outdoor activities.
Home in Miller
4.83 out of 5 average rating, 36 reviews

Entire House With Pool - Backyard Beach Getaway

CrystalRating, 5 stars5 months ago
This home was super cozy for my big family. Everything was clean, comfortable, and the way it is set up makes you feel right at home. This home had everything we needed. TV’s, kitchen items, recommendations, and even fun family games and activities to do. Every time I visit the area I’ll be checking to see if it’s available. 10/10
Superhost
Home in Miller
4.93 out of 5 average rating, 137 reviews

Bayless Dune Lodge at West Beach - Indiana Dunes!

KevinRating, 5 stars1 week 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!
Guest favorite
Home in Carol Stream
4.86 out of 5 average rating, 7 reviews

Spacious 4 Bed/3.5 Bath Sleeps 8+

CarmenRating, 5 stars6 months ago
Beautiful house very clean and comfortable. We'll be back very soon

Weekly house rentals

Guest favorite
A lakefront view reveals a charming house with a porch and multiple seating areas on the lawn. A private dock extends into the water, accommodating a pontoon. Green trees provide shade, while an American flag gently waves in the breeze.
Home in Valparaiso
4.94 out of 5 average rating, 127 reviews

Lakefront House, Pontoon, Deck, Fire Pit & More!

JamesRating, 5 stars1 week ago
Leah was a phenomenal host, very responsive and fast with her replies to my questions. The place was super comfortable and welcoming. It was peaceful and quiet just as advertised. Had a wonderful stay!
Superhost
An inviting outdoor space features a lush green lawn with well-maintained trees and shrubs lining the property. A gravel driveway leads towards a white ranch-style home and a garage, providing access to a spacious and quiet area surrounded by nature.
Home in Round Lake Beach
4.82 out of 5 average rating, 122 reviews

Modern 3 bedroom house, quiet residential street.

JoanRating, 5 stars1 month ago
Very clean and comfortable, nice neighborhood and not too far from our venue. Bikash was super responsive and even recommended a great place to try out Chicago deep dish pizza.
Guest favorite
A well-lit entryway showcases a wooden staircase with elegant railing leading to upper levels. The dark front door contrasts with the light walls, while a stylish cabinet and framed photos add character to the space, inviting guests into the home.
Home in Roscoe Village
4.92 out of 5 average rating, 282 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

MontiraRating, 5 stars4 days ago
2nd time staying at Sharleen’s place—wonderful experience! We like location, friendly and quiet neighborhood, walkable to restaurants. We would recommend to guests looking for a space in Roscoe. 🙂
Superhost
The exterior of the two-story Cape Cod-style home features a charming brick façade, accented by blue shutters. A small, landscaped slope leads to a welcoming entry, framed by greenery. An upper deck with a railing offers an outdoor space for relaxation.
Home in Miller
4.81 out of 5 average rating, 58 reviews

Indiana Dunes Park Getaway w/Firepit, Near Beach

NicholasRating, 5 stars8 months ago
Kelly’s place was wonderful. There’s a lot to enjoy here from a wonderful backyard with a fire pit, a lovely front porch, a chill side porch with a grill, a second floor balcony, and a sun room. The place was perfectly clean when I got there and they so nicely left out plenty of clean towels and sweatshirts for myself and my friends. I would definitely stay again if I came back to the area!
Top guest favorite
A bright dining area features a long wooden table surrounded by six blue chairs. A modern chandelier hangs above, illuminating the space. In the background, a staircase leads to the upper level, while a cozy living area is visible, providing an open and inviting layout.
Home in Wicker Park
4.97 out of 5 average rating, 33 reviews

Wicker Park 6bd/4ba, Steps from Cta, Parking Incl

LaureenRating, 5 stars1 month ago
The location alone makes this home worth booking. Add that there’s ample room for family/friends and it’s a gem in the middle of a great Chicago neighborhood. We were a group of six and loved every minute.
Guest favorite
A spacious living area features plush sofas arranged around a decorative coffee table. A large flat-screen TV is mounted above a stylish fireplace. Floor-to-ceiling windows allow natural light to fill the room, where a patterned area rug adds depth and texture.
Home in Waukegan
4.8 out of 5 average rating, 246 reviews

Modern home. Near naval base, Six flags and Casino

KeiryRating, 5 stars1 week ago
Nice home, rooms were pretty spacious & good for a family stay. Very peaceful!
Guest favorite
A large, two-story home is presented with a brown wooden exterior. A spacious driveway leads to a wooden garage door, flanked by low-maintenance landscaping featuring shrubs and decorative plants. Large windows above the entrance allow natural light to illuminate the entryway.
Home in Third Lake
4.93 out of 5 average rating, 14 reviews

Home for flexible term rental

AlanaRating, 5 stars1 week ago
This place was perfect for my husband, our ten year old and my mother and I. Plenty of space and privacy for my mother on second floor, and for us on the first floor. Everything was well designed- there was plenty of flexible and very comfortable seating in the living room and bedrooms for hanging out, and also around the dinner table. So much natural light, and free of clutter, yet it felt homey and like someone cared about their space, not just furnished as a rental business. The neighborhood was great for playing pass in the cul de sac, or across st at park and playground, and lovely for walking. Kitchen appliances were primo, and we found everything we needed. Thank you for such an enjoyable stay!
Top guest favorite
A spacious ranch house is depicted, surrounded by matured trees and a well-maintained lawn. The facade features a combination of brick and siding, with a large garage and a welcoming front porch. Sunlight filters through the leaves, creating a serene atmosphere.
Home in Itasca
5 out of 5 average rating, 52 reviews

RANCH, House-tel: updated full kitchen, comfy beds

JanetRating, 5 stars3 days ago
This was our second time staying at Jehu's home in Itasca, IL. We have family and friends nearby so the location is perfect. The beds are comfortable, and the house is very clean. Having bottled water, coffee, a variety of beverages and snacks at our disposal was a plus. Jehu was very responsive to any questions we had. We would definitely book this property again for our next visit to the Chicagoland area.

Private house rentals

Top guest favorite
The exterior of a historic house features a two-story facade with a gabled roof and large windows on the first level. Lush greenery surrounds the property, creating a welcoming atmosphere and enhancing the home’s charm.
Home in Oak Park
5 out of 5 average rating, 5 reviews

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath

VinceRating, 5 stars4 months ago
This is the 2nd time this year we rented from Michael. He continued to impress with the responsiveness. This time we filled the whole house, all bedrooms and both floors, 12 in total, mix of kids and adults. We decorated for Christmas, made it feel like we were home for the holidays. We walked all around the neighborhood, got coffee in the morning, fresh bread from a fabulous bakery in Downtown Oak Park and always felt safe and enjoyed the friendly neighborhood. The home and bedrooms were warm when you wanted them warm during the day and cool at night to sleep in. Kitchens were well equipped and all the appliances worked perfectly. The tankless water heater was a blessing when we were all trying to get out for a family event. At one point we realized that we were out of trash bags on Christmas morning. Michael had them there in less than 30 minutes. Over the top responsiveness. Being 10 minutes from the Eisenhower makes this convenient to either Downtown or Oak Brook.
Guest favorite
The kitchen features modern white cabinetry with sleek countertops and stainless steel appliances. A central island with a wooden top provides additional workspace. Two woven barstools are situated at the island, and natural light enters through the dual windows, illuminating the space.
Home in Naperville
4.87 out of 5 average rating, 130 reviews

Home away from home

JordanRating, 5 stars1 month ago
We couldn’t have asked for a better home for our Spring Break. We last minute booked this home, and checked in 45 later but you would have never known by how welcoming Vytauta made it. Beds were very comfortable, backyard was great, we felt right at home.
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, 48 reviews

Big Family Home with 4 King Beds

GabrielRating, 5 stars4 days ago
I will be recommending this place to everyone for a nice get together. The neighborhood was nice and quiet and it is a beautiful place to relax or to have as an activity weekend. Plenty of stuff to do
Superhost
A gray cottage is surrounded by a spacious lawn, featuring well-maintained green shrubs and a small shed nearby. Large windows provide glimpses of the inviting interior. The area is framed by trees, offering a sense of privacy and tranquility.
Home in Wonder Lake
4.9 out of 5 average rating, 10 reviews

Just Off The Lake Comfort

NatalieRating, 5 stars8 months ago
I had an incredible stay at Wanda's house! From the moment I arrived, I was greeted with warmth and hospitality. The home was exactly as described, even better in person—spotlessly clean, beautifully decorated, and equipped with everything I needed for a comfortable stay. The location was perfect for the wedding we were attending that weekend. I especially loved how cozy and convenient it was. Wanda went above and beyond to ensure I had a great experience, providing flexible check in/out times, ample snacks, and an abundance of amenities to help it feel more like home. Communication was smooth and prompt, and helped with everything we needed. I highly recommend Wanda's place to anyone looking for a relaxing and cozy stay in Wonder Lake! I can’t wait to come back.
Guest favorite
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
4.89 out of 5 average rating, 125 reviews

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

NathanRating, 5 stars3 weeks ago
It was a comfortable stay. Tons to do in the area. Can’t go wrong!
Superhost
A comfortably arranged living room features a gray sofa with multiple cushions and two teal accent chairs. Natural light enters through large windows dressed in light curtains, while a wooden floor adds warmth to the space. A flat-screen TV is mounted on the white wall.
Home in Markham
4.73 out of 5 average rating, 124 reviews

The Country Life! Entire House.

DeniseRating, 5 stars1 month ago
Cathy was a great host, very responsive! House was great, it accommodated our family size perfect. The only thing in my opinion that was missing was washer and dryer access in the home. We were traveling with toddlers and couldn’t wash a load of clothes. But aside from that everything else was great.
Top guest favorite
A cozy living area is furnished with a mix of seating options, including a spacious sofa and several armchairs. A polished hardwood floor complements the light-colored walls and large windows, which provide ample natural light. Decorative items and artwork enhance the inviting atmosphere.
Home in DeKalb
4.91 out of 5 average rating, 220 reviews

Country charmer house near NIU

MadisonRating, 5 stars1 month ago
This is our second year staying at this beautiful and convenient Airbnb. Only 15 minutes from the NIU Convocation Center! Close to a great pizza place that will deliver to the Airbnb. Cynthia is very responsive and very flexible. We love this space!
Guest favorite
An open living space is shown, featuring a light gray sofa with decorative throw pillows facing a marble coffee table. In the background, a modern kitchen with wooden cabinets and stainless steel appliances is partially visible, with a dining area beyond.
Home in Valparaiso
4.96 out of 5 average rating, 26 reviews

Serene Settings

JoeRating, 5 stars2 weeks ago
A hidden gem! Perfect hideaway for city and country folks alike.

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Westchester
  6. House rentals