House vacation rentals in Homewood

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Popular amenities for Homewood 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 stars2 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 Schererville
4.93 out of 5 average rating, 44 reviews

Cozy house in Schererville

DanielRating, 5 stars2 weeks ago
kates house was excellent and clean extremely comfortable for a work trip.
Guest favourite
Home in Munster
5 out of 5 average rating, 10 reviews

Munster hide away

ChristopherRating, 5 stars1 month 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 favourite
Home in Chesterton
4.98 out of 5 average rating, 40 reviews

Pool House near the Indiana Dunes

KrishnaRating, 5 stars4 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!
Guest favourite
Home in Bloomingdale
4.95 out of 5 average rating, 43 reviews

Whole House with a Hot Tub and Giant Pool!

ChristopherRating, 5 stars3 weeks 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 Miller
4.83 out of 5 average rating, 35 reviews

Entire House With Pool - Backyard Beach Getaway

CrystalRating, 5 stars2 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 stars5 months ago
Damani was an amazing host and communicator. He was very accommodating and the place was amazing. Highly recommend!
Guest favourite
Home in Plainfield
4.93 out of 5 average rating, 75 reviews

Large Spanish style Home (w/inground pool)

DevonRating, 5 stars5 months ago
House was lovely. I enjoyed the homes decor. Every day I woke up with something else I loved. The house had everything we needed. Only thing I wished the pool heater was working and the pillows were flat. I would definitely stay here again.

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 stars2 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!
Guest favourite
Home in Roscoe Village
4.92 out of 5 average rating, 271 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

JaleesaRating, 5 stars3 weeks ago
Sharlene was an excellent host. She gave us suggestions on what we could do in the area and was very responsive. Her home looked just like the pictures and was very clean. We had a hiccup at checkout and she was very accommodating. We would definitely book her home again.
Superhost
Home in Miller
4.81 out of 5 average rating, 58 reviews

Indiana Dunes Park Getaway w/Firepit, Near Beach

NicholasRating, 5 stars5 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!
Guest favourite
Home in Wrigleyville
4.91 out of 5 average rating, 174 reviews

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

RonRating, 5 stars2 months ago
Ami was great to work with as proactively communicated with detailed instructions which made the trip seamless for our group. She was very quick in responding to any questions we had during our stay (Where is the gas key for the fireplace?) and I would highly recommend staying at this residence in the heart of Wrigleyville. She is great to work with and makes the stay pleasant and inviting.
Guest favourite
Home in Lake View
4.95 out of 5 average rating, 182 reviews

Wrigleyville Greystone

MarkRating, 5 stars1 month ago
The place was in a beautiful, quiet neighborhood, and clean and very comfortable for our family of 5 adults. Mark was very accommodating and let us check in two hours early as we arrived in town before we expected to, and it was raining and didn't want to get wet walking around outside. The location was great as we were in town for the NHL Winter Classic, and it was an easy walk to Wrigley Field. Also, lots of great restaurants within walking distance. We were also celebrating Christmas with our family and to our wonderful surprise, there was a tree and many other festive decorations up that made it extra special! We would definitely stay in this location again while in Chicago.
Guest favourite
Home in Valparaiso
4.95 out of 5 average rating, 20 reviews

Serene Settings

VinzentRating, 5 stars5 days ago
We used the house as accommodation for a job we had nearby, for our purposes it was perfect
Guest favourite
Home in Justice
4.94 out of 5 average rating, 222 reviews

3 Kng, 1 Qn, 1 Full, 3AirBd|Basktbll Crt|FreePrkin

NathanRating, 5 stars2 weeks ago
Another fantastic stay at Michael’s house! Clean, spacious, and in a nice quiet neighborhood. We would love the opportunity to come back and enjoy this house in the future!
Guest favourite
Home in Itasca
5 out of 5 average rating, 49 reviews

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

DianaRating, 5 stars2 months ago
What a great Airbnb! Easy to access downtown Chicago but without the hassle of being downtown. Everything was super clean, the beds are comfortable and the neighborhood is quiet and easy to walk (especially if you have pets). Highly recommend!

Private house rentals

Guest favourite
Home in Aurora
4.94 out of 5 average rating, 36 reviews

Spacious family friendly home away from home

BrendaRating, 5 stars1 month ago
This was perfect for our needs for 6 people. There was plenty of space for sleeping and just hanging out without feeling crowded. It was clean and very neat. It was also nice to have a Roku TV so we could stream our apps. We had a great visit.
Superhost
Home in Oak Park
5 out of 5 average rating, 4 reviews

Sleeps 12 Comfortably in 8 Bedrooms 3 Full Bath

VinceRating, 5 stars1 month 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 favourite
Home in Old Town
4.98 out of 5 average rating, 54 reviews

Extravagant Old Town Home w/ Sauna, Rooftop Lounge

ElizabethRating, 5 stars3 months ago
This house in old town is pure luxury. The home is gorgeous and wonderfully comfortable. The host is very generous with lots of extra supplies and linens We arrived to a bottle of wine and snacks beautifully laid out for us. The elevator and sauna were also fun extras. The house is immaculate; it is located on a very safe street with fun and shops just two blocks away. Attached parking for two cars! The host is very accommodating. We will be staying here again!!
Guest favourite
Home in Naperville
4.87 out of 5 average rating, 128 reviews

Home away from home

SusieRating, 5 stars2 months ago
Vytautas is a very welcoming, responsive host. He responded quickly to questions about the property and my stay in particular. The property is very convenient to Naperville and highways connecting to the greater area. It was easy to enter the front door and the home was toasty warm on a cold Chicago night when I arrived. It was great to have the private back yard with my dog. I think it would be fun to be there in summer when the trees have leaves and the weather is warm. The only down side for people who want to have meals there is that you have to set up a table (which is folded up in the back room) and chairs to have a group sit down. This wasn't a problem for me because I have family in the area and went to their homes for meals. And I believe the table would be large enough for 6 if you have that many people. I wouldn't hesitate to stay there again. Thank you, Vytautas
Guest favourite
Home in Elmhurst
5 out of 5 average rating, 36 reviews

Big Family Home with 4 King Beds

AlisonRating, 5 stars1 week ago
Syed was a great host and made everything about our stay super easy and comfortable! He was always very quick to respond and I felt he was always available and ready to help if needed. I rented the property for a girls weekend, and it had plenty of space for all 16 women. I would definitely recommend this property! We had a fantastic experience.
Superhost
Home in Hermosa
4.8 out of 5 average rating, 5 reviews

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

ShauniceRating, 5 stars3 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
4.91 out of 5 average rating, 115 reviews

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

SarahRating, 5 stars2 weeks ago
Wonderful stay for our girls trip! Quiet neighborhood! House was a perfect layout & clean! Fast uber trip downtown if not wanting to drive! Would definitely stay again.
Superhost
Home in Gary
4.88 out of 5 average rating, 33 reviews

The Blue House: Family Retreat

KasiyahRating, 5 stars1 week ago
Very homey place and they even decorated for Valentine’s Day I loved it!! Will be booking again!

Quick stats about house rentals in Homewood

  • Total rentals

    30 properties

  • Nightly prices starting at

    $71 CAD before taxes and fees

  • Total number of reviews

    770 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

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