House holiday rentals in Homewood

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Popular amenities for house rentals in Homewood

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 stars4 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
4.94 out of 5 average rating, 51 reviews

Cozy house in Schererville

CarlosRating, 5 stars4 days 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 favourite
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 favourite
Home in Chesterton
4.98 out of 5 average rating, 40 reviews

Pool House near the Indiana Dunes

KrishnaRating, 5 stars6 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
4.94 out of 5 average rating, 47 reviews

Whole House With Hot Tub And Spacious Bedrooms

KarinaRating, 5 stars1 week 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
Superhost
Home in Miller
4.83 out of 5 average rating, 35 reviews

Entire House With Pool - Backyard Beach Getaway

CrystalRating, 5 stars4 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
Guest favourite
Home in Plainfield
4.93 out of 5 average rating, 75 reviews

Relaxing Spanish style Home (w/inground pool)

DevonRating, 5 stars7 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.
Guest favourite
Home in Schaumburg
4.95 out of 5 average rating, 20 reviews

Paradise 4BR w/ Pool & Games

JasonRating, 5 stars7 months ago
We really enjoyed our stay at this beautiful home. It is close to everything. The place is clean and very organized. Lily and Nathan has been wonderful and very responsive and communicated well with us. I definitely recommend this place when you visit Schaumburg. Thank you guys for everything.

Weekly house rentals

Guest favourite
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!
Guest favourite
Home in Roscoe Village
4.92 out of 5 average rating, 280 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

BrigidRating, 5 stars2 weeks ago
We enjoyed preparing pizzas from scratch in the perfectly sized kitchen with our adult kids who live in Chicago and their friends. There was plenty of space to sit around the spacious kitchen island and talk while cooking. The whole experience was made even better by using the Wolf stove top and Bosch wall-mount oven, which produced perfectly crisp crust and tasty toppings. The neighborhood felt safe and peaceful while providing everything we needed within walking distance. Parking was also easy. We had no trouble finding a space in front of the house all 4 days we were there. As a special bonus, a new chocolate cafe opened a few days ago (Hotel Chocolat Velvetiser Cafe) and is just a short walk away! We had a great time in this lovely home.
Superhost
Home in Miller
4.81 out of 5 average rating, 58 reviews

Indiana Dunes Park Getaway w/Firepit, Near Beach

NicholasRating, 5 stars7 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, 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 favourite
Home in Whiting
4.84 out of 5 average rating, 152 reviews

The Spa of Downtown Whiting

SantiagoRating, 5 stars5 days ago
a really awesome place. I highly recommend this place.
Top guest favourite
Home in Lake View
4.95 out of 5 average rating, 183 reviews

Wrigleyville Greystone

ThomasRating, 5 stars1 month ago
Fantastic place in an awesome location. Very walkable part of town and a great spot to easily get to Wrigley Field. Found a number of great bars and restaurants in walking distance during our stay. Would definitely stay here again!
Guest favourite
Home in Valparaiso
4.96 out of 5 average rating, 25 reviews

Serene Settings

JoyRating, 5 stars2 weeks ago
Anna’s place was very welcoming. It was a perfect place for our family to visit. We enjoyed the large yard. It was perfect for our dogs to play. Anna had dog biscuits and toys for our dogs. There was a walking path close by..We would definitely stay here again.
Guest favourite
Home in Justice
4.93 out of 5 average rating, 224 reviews

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

PaulRating, 5 stars2 months ago
Great place with plenty of space. Our family really enjoyed Michael’s home.

Private house rentals

Guest favourite
Home in Aurora
4.92 out of 5 average rating, 38 reviews

Spacious family friendly home away from home

YennyRating, 5 stars2 months ago
Amazing experience felt just like home.
Guest favourite
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 favourite
Home in Elmhurst
5 out of 5 average rating, 45 reviews

Big Family Home with 4 King Beds

LauraRating, 5 stars5 days ago
We were a family of 14. My 3 adult Kids and their spouses, my 6 grandkids, ages 2 to 21 years old. The number of beds fit us comfortably. The game/activity room was a hit with the kids especially. The dining room and kitchen dinning areas fit us well. We did have some issues, that Syed responded to quickly. Syed is a very nice man and a great host, however the house is in need of some minor repairs, the garbage disposal didn’t work, cabinets in the kitchen need repair, we had ants on the counter in the kitchen that we had to spray to get rid of. The railing going upstairs was coming out of the wall. Syed responded quickly to rectify most of these things. The house and bathrooms are clean, but the tub and showers need to be recaulked, They are showing signs of mold. I spoke with Syed about these issues and he assured me they will be taking care of all these things. I believe that he will. Overall it was a great place for a large family. It met our needs for the 4 days we were there.
Superhost
Home in Blue Island
4.81 out of 5 average rating, 193 reviews

Warm and comfortable inviting Suburban home !

MarcusRating, 5 stars5 days ago
Always a pleasure staying with at Rich’s place
Guest favourite
Home in Naperville
4.89 out of 5 average rating, 125 reviews

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

NathanRating, 5 stars2 weeks ago
It was a comfortable stay. Tons to do in the area. Can’t go wrong!
Superhost
Home in Gary
4.87 out of 5 average rating, 45 reviews

The Blue House: Family Retreat

AlexisRating, 5 stars1 week ago
Clean and kid friendly! Just as described. Perfect place to hang our Easter vacation with our group of 13!! Everyone felt comfortable and accommodated. Only thing I’d change if I could, more pillows! We’re a pillow loving family. Otherwise everything was great!!
Guest favourite
Home in Miller
4.9 out of 5 average rating, 29 reviews

Rivera House-fun and comfort steps from the beach

EmilyRating, 5 stars10 months ago
We had an absolutely lovely time! We took a family trip and the house was perfect for 6 adults and 5 kids. The beach was super close to walk to. The large house was perfect for everyone to have their own space. The spacious living room/kitchen was a great place to spend family time cooking, playing games, eating, etc where we could all be together but doing separate things. There were plenty of towels for everyone for that many days which surprised me! Inga had thought of everything! There was all the extras you might need too like cooking basics, sunscreen, flashlight, bug spray, beach chairs, toys, umbrellas! And the espresso machine was also a hit with our family! Thank you so much Inga for having us!! We made memories that will last a lifetime in your beautiful home!
Superhost
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.

Quick stats about house rentals in Homewood

  • Total rentals

    30 properties

  • Nightly prices starting at

    £38 before taxes and fees

  • Total number of reviews

    790 reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

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  5. Homewood
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