
House vacation rentals in Westchester
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Top-rated house rentals in Westchester
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Vacation rentals for every style
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Popular amenities for Westchester house rentals
House rentals with a pool

2-Acre Highland Park Retreat with Heated Pool ~ 5*
We were in town for Thanksgiving visiting family with our dogs for 4 nights. Communication with host was great. The house was very clean, well furnished (we cooked the Thanksgiving meal there), recently renovated kitchen (huge kitchen island) with high end appliances, and yes there are 6 bedrooms (some small but nice). Rooms are split between three floors so everyone had room/privacy. Backyard with pool was great, lots of space for dogs, everything is fenced in but the front which was not a problem as the house is on a dead-end street with very little traffic. This is definitely a superhost home, all your condiments, lots of nice touches and snacks/gifts. We will definitely stay there again on our next visit to family in Chicago. House is locate between 41 and 94 making travel around Chicago easy.

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!

No Cleaning Fee - Whole House With Hot Tub
My team & I had an excellent stay at Moiz's property during the Frosty Faustings tournament weekend! extremely spacious and clean.

Highwood Haven
The house is great, it's a wonderful set up for midsize groups. The water quality is not great, I'm guessing theyre on wells. there are probably 15 TVs which is awesome. The hot tub never got hot enough for my taste. all around a wonderful trip.

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!

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

Luxury Cabin in Lakeview
Damani was an amazing host and communicator. He was very accommodating and the place was amazing. Highly recommend!

Bayless Dune Lodge at West Beach - Indiana Dunes!
Let me start by saying that I have rented several Airbnb homes but this experience was by far the best. Cullen was a very personable and gracious host. The house was nicely decorated, had comfortable beds, and was well stocked with towels and paper products. There was also a basket of assorted snacks and a handwritten welcome note upon our arrival. There was plenty of room for our party and a good amount of parking outside. Since our visit was in January we couldn't take advantage of the backyard amenities but they appear to be very nice for a summer backyard bbq and great family fun. All this said, Cullen and his home are a 10 out of 10 that we definitely recommend !
Weekly house rentals

Lakefront House, Pontoon, Deck, Fire Pit & More!
Very pleasant stay over Thanksgiving while visiting family. Quiet, peaceful lake setting (even though it was very cold out and no swimming in the lake at 20 degrees!).. It was a good place to rest after the noise and activity of our large family 3 day gathering!

Modern 3 bedroom house, quiet residential street.
Beautiful, clean home. We loved it!

Duplex Home RoscoeVillage/Wrigley Free St Parking
Sharleen is such a nice person and host. Her place is really accommodating and comfortable, our team had a great time at her home. Thank you, Sharleen.

Indiana Dunes Park Getaway w/Firepit, Near Beach
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!

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
Dennis is a great host and quick to respond when I needed help getting inside. The location is quiet, affordable, and enjoyable with plenty of amenities and things to do. I would recommend staying here to anyone.

Harbor Hideout 4/3 Waterfront w/ Wet Bar Apartment
The host were amazing. The one time I had a question they were quick and very nice. Great customer service to make sure our stay was perfect. The location is beautiful. I definitely want to stay in this house during the summer. Highly recommended

Serene Settings
this is my second time staying at one of Anna's properties, and I have to just say that it is quite literally a home everytime you walk in. everything is within range of one another, there's always so much to do in the immediate area, and the thing that sticks out most about this particular property is that it is so unbelievably quiet.
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.

Big Family Home with 4 King Beds
wanted to stay longer but vacations are short, will be back in a future

Just Off The Lake Comfort
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.

2Level Home 20 Mins to Dt Chicago!-Jacuzzi-Sleeps8
Book the house! It’s beautiful! Like every part of it. And it’s has everything you need inside. Kitchen is fully loaded to cook and all rooms and spotless. The home is top tier and the host and very nice.

California King Bed | Fast Wi-Fi | 75" Smart TV
We had a wonderful reunion weekend at Vic's place. It was private, comfortable, and had good amenities for 6 people. Vic himself was very responsive to all our custom requests and all guests enjoyed the place. Thank you, Vic for making it memorable.

Luxury Home Away from Home
Another great stay. Cindy was great and the house is awesome.

Private Get A Way
This is beyond 5 stars! The home is very clean, comfortable, and spacious for a group. The Naval base is no more than a 15-minute drive and the train station to go into downtown Chicago is only a 10-minute drive. (The train ride to Union Station is 1 hour.) There are plenty of restaurants not too far from the house too. If you do not have a car, Ubers and taxis were available within 5-10 minutes after requesting one. We loved the home. The beds were comfortable, every room and fixture was clean, there were plenty of kitchen accessories, towels, coffee pods, laundry pods, hand soap, spices, toilet paper, etc. The only item we bought was napkins, which was totally fine & to be expected. The fireplace was an added bonus. especially since the weather was cold & snowy outside. There are board games such as Monopoly & cards, The lighting was good too, especially for putting on makeup in the bathroom. Quiet neighborhood. Would definitely stay there again! Thank you, Nancy!

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!
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