House vacation rentals in Westchester

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Popular amenities for Westchester house rentals

House rentals with a pool

Guest favourite
Home in Highland Park
4.92 out of 5 average rating, 142 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

JeffRating, 5 stars3 months ago
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.
Guest favourite
Home in Chesterton
4.98 out of 5 average rating, 40 reviews

Pool House near the Indiana Dunes

KrishnaRating, 5 stars5 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 favourite
Home in Bloomingdale
4.93 out of 5 average rating, 44 reviews

No Cleaning Fee - Whole House With Hot Tub

ChristopherRating, 5 stars1 month ago
My team & I had an excellent stay at Moiz's property during the Frosty Faustings tournament weekend! extremely spacious and clean.
Superhost
Home in McHenry
4.89 out of 5 average rating, 89 reviews

Highwood Haven

DavidRating, 5 stars3 weeks ago
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.
Guest favourite
Home in McHenry
5 out of 5 average rating, 12 reviews

Paradiso Vacation

TimothyRating, 5 stars1 month ago
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!
Superhost
Home in Miller
4.83 out of 5 average rating, 35 reviews

Entire House With Pool - Backyard Beach Getaway

CrystalRating, 5 stars3 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 Lincoln Park
4.87 out of 5 average rating, 53 reviews

Luxury Cabin in Lakeview

Varun Rating, 5 stars6 months ago
Damani was an amazing host and communicator. He was very accommodating and the place was amazing. Highly recommend!
Superhost
Home in Miller
4.93 out of 5 average rating, 135 reviews

Bayless Dune Lodge at West Beach - Indiana Dunes!

DianaRating, 5 stars2 months ago
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

Guest favourite
Home in Valparaiso
4.95 out of 5 average rating, 125 reviews

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

RubyRating, 5 stars3 months ago
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!
Superhost
Home in Round Lake Beach
4.82 out of 5 average rating, 120 reviews

Modern 3 bedroom house, quiet residential street.

AleidaRating, 5 stars2 months ago
Beautiful, clean home. We loved it!
Guest favourite
Home in Roscoe Village
4.92 out of 5 average rating, 274 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

marcioRating, 5 stars3 weeks ago
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.
Superhost
Home in Miller
4.81 out of 5 average rating, 58 reviews

Indiana Dunes Park Getaway w/Firepit, Near Beach

NicholasRating, 5 stars6 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 favourite
Home in Wicker Park
4.97 out of 5 average rating, 32 reviews

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

LaureenRating, 5 stars3 days 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 favourite
Home in Waukegan
4.8 out of 5 average rating, 242 reviews

Modern home. Near naval base, Six flags and Casino

JoshRating, 5 stars5 days ago
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.
Superhost
Home in Fox Lake
4.9 out of 5 average rating, 217 reviews

Harbor Hideout 4/3 Waterfront w/ Wet Bar Apartment

GabrielleRating, 5 stars2 weeks ago
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
Guest favourite
Home in Valparaiso
4.95 out of 5 average rating, 22 reviews

Serene Settings

FranciscoRating, 5 stars1 week ago
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

Superhost
Home in Oak Park
5 out of 5 average rating, 4 reviews

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath

VinceRating, 5 stars2 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.
Top guest favourite
Home in Elmhurst
5 out of 5 average rating, 42 reviews

Big Family Home with 4 King Beds

NestorRating, 5 stars1 week ago
wanted to stay longer but vacations are short, will be back in a future
Superhost
Home in Wonder Lake
4.9 out of 5 average rating, 10 reviews

Just Off The Lake Comfort

NatalieRating, 5 stars7 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.
Superhost
Home in Hermosa
4.8 out of 5 average rating, 5 reviews

2Level Home 20 Mins to Dt Chicago!-Jacuzzi-Sleeps8

ShauniceRating, 5 stars4 months ago
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.
Guest favourite
Home in Naperville
4.9 out of 5 average rating, 118 reviews

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

UrmiRating, 5 stars1 month ago
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.
Top guest favourite
Home in DeKalb
5 out of 5 average rating, 34 reviews

Luxury Home Away from Home

ChrisRating, 5 stars2 months ago
Another great stay. Cindy was great and the house is awesome.
Top guest favourite
Home in Libertyville
5 out of 5 average rating, 25 reviews

Private Get A Way

SherryRating, 5 stars2 months ago
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!
Top guest favourite
Home in DeKalb
4.91 out of 5 average rating, 219 reviews

Country charmer house near NIU

MadisonRating, 5 stars1 week 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!

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