
House vacation rentals in Westchester
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Top-rated house rentals in Westchester
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Westchester house rentals
House rentals with a pool

Cozy house in Schererville
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.

Munster hide away
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.

Pool House near the Indiana Dunes
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!

Whole House With Hot Tub And Spacious Bedrooms
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

Paradiso Vacation
My family and I had a great time. The home exceeded our expectations and we all had tons of things to do. We attended local Groundhog's Day festivities and just enjoyed our time together in a wonderful home away from home. We definately recommend!

Grand 1800s Victorian Gem: Updated/by Downtown
My friends and I had a wonderful stay at Deirdre’s home! It’s a gorgeous property with lots of charm and space, and so many great amenities (theater room, claw foot bathtub, Sonos speakers, ample parking, etc.). Deirdre was also very responsive throughout the process and even helped us with a more flexible checkout time. Absolutely recommend visiting her home, we’re already wishing for another trip!

Entire House With Pool - Backyard Beach Getaway
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

Bayless Dune Lodge at West Beach - Indiana Dunes!
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

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

Modern 3 bedroom house, quiet residential street.
Nice and cozy. Few minutes away from everything you need, and a 5 minute walk from the lake.

Duplex Home RoscoeVillage/Wrigley Free St Parking
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. 🙂

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

Modern home. Near naval base, Six flags and Casino
Nice home, rooms were pretty spacious & good for a family stay. Very peaceful!

Home for flexible term rental
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!

Harbor Inn - Harbor Master Villa
A lovely cottage in a beautiful and serene landscape. The harbor is on the side of the cottage and the Illinois River is immediately across the street. A single female traveler, I found the area beautiful and neighbors were friendly. The cottage was clean and spacious. If you go, do stop by the welcome desk-the people there were friendly and kind! Would stay here again in the summer as I’m certain the place is hopping! Totally recommend staying here no matter the season.

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

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath
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.

Spacious 4 Bed Room suburban home
Uthuman’s was a great place to stay! It was cozy! There were plenty of towels available. The beds were comfy and everything was clean. I had quick responses to any questions I had. I would recommend staying here!

Home away from home
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.

California King Bed | Fast Wi-Fi | 75" Smart TV
It was a comfortable stay. Tons to do in the area. Can’t go wrong!

Luxury Home Away from Home
We were very pleased with our accommodations. Clean, just about anything you needed to make a meal, bake, or just sit back and order in. many restaurants just a short drive away.

The Country Life! Entire House.
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.

Country charmer house near NIU
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!

Serene Settings
A hidden gem! Perfect hideaway for city and country folks alike.
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- Six Flags Great America
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park Zoo
- Wilmot Mountain Ski Resort
- Flossmoor Golf Club
- Willis Tower
- Museum of Science and Industry
- Wicker Park
- Lincoln Park
- Chicago History Museum
- Skokie Country Club
- Illinois Beach State Park
- Brookfield Zoo
- Promontory Point