
House holiday rentals in Highland Park
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Top-rated house rentals in Highland Park
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Holiday rentals for every style
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Popular amenities for house rentals in Highland Park
House rentals with a pool

Abbey Springs Home! Hot Tub + Golf Cart
A wonderful home that was well appointed, clean & a great location! We hosted Easter here with my adult Kids and grandson. We all enjoyed the beautiful surroundings and all the wildlife-many deer and even a coyote! So much room and a great layout for us to enjoy the home together!

Rosemont 4BD2BA house with Pool
Mike was very responsive leading up to our stay and very helpful whenever I had any questions about the property. The home was very clean and well maintained. Would recommend!

Now Open: Heated Pool with Entire House
Moizs was an amazing host. Very accommodating, quick response, had some great recommendations for local restaurants, shopping, etc. Bloomingdale is a cute and nice suburb of Chicago. We had a great trip and we will definitely be back.

Oasis on Oak | Private In-Ground Pool | Hot Tub
House was great and matches the description and photos. House is spacious, good for a group of 6-7 people and private from other neighbors. It’s also less than 10 minutes from downtown Lake Geneva. It is an ideal house if you are looking for a quiet weekend retreat, close to the areas activities. In addition, the host is responsive and helpful. Looking forward to our next stay with you all!

Schaumburg Oasis:Private Pool & Enchanted Garden
They were a fantastic host, very responsive to every question and anything we needed. The location is quiet and amazing, great place to relax and enjoy time. love the pool! Will definitely stay again. 100% recommend!

Relaxing Summer Getaway near Lake Geneva w/ Pool
The house was a perfect fit for my family of 8. The amenities were great and Nicolet provided excellent communication.

Beautiful Spanish style Home (w/inground pool)
Stayed here the night before my wedding with my siblings who stayed the night of the wedding. We hosted our getting ready portion here for the morning of the wedding and Olinka and Daniel were gracious enough to allow us to stay in their beautiful home. Made for gorgeous pictures and a comfortable stay both nights. Thank you!!

Beautiful 137 Year Old Farm Home (3night min)
Beautiful and eclectic home. It was perfect for our group of girls visiting from all over the U.S to attend our HS Reunion. Plenty of lovely spaces to gather or a private, quiet nook to read or rest. The pool was wonderful. Beds were super comfortable. Kitchen was large enough and well stocked to prepare meals. Andy was very responsive with any issues or questions. Highly recommend!
Weekly house rentals

2BR Lake House | Lake Toys | Views | Dog Friendly
We had the pleasure of staying here over our anniversary weekend with our 2 kiddos; it was our first vacation just our little family and it's was fantastic. Cristle was so helpful and went above and beyond to help us out when we had some issues on our end leading up to our trip. She was very thoughtful and kind and that alone was worth the 5 star rating. The home was very well kept and clean and had everything we needed for a nice relaxing weekend. We had a lot of fun out on the paddle boat and playing in the yard. The screened in porch was also a nice bonus. Our girls enjoyed the park and playing the sand. Overall it was a very nice stay and we'd love to go back sometime soon.

6 Kings | Ping-Pong | Gazebo!
My friends and I really enjoyed our stay. Everything was exactly how they described. Quick response from the hosts, I highly recommend this place. Definitely going back 💃

Lake House Retreat Near Navy Base
Larry was a very accommodating and responsive host! The place was amazing and exactly as described. Plenty of room, amenities, and beautiful views. He made sure we had plenty of supplies and all the stuff for Smores!

Culinary DREAM - Pizza Oven/BBQ/Smoker
Great house. Very clean and spacious.

The Oak Tree Ranch
I had an amazing experience! From the moment I arrived, everything was seamless. The check-in process was smooth, and the host was incredibly responsive and welcoming. The space itself was spotless, well-decorated, and had all the amenities I needed for a comfortable stay. The bed was cozy, the kitchen was nice, and the little touches-like fresh towels made big difference. I couldn't have asked for a better place to stay. It truly felt like a home away from home. I would absolutely book again and highly recommend it to anyone visiting the area!

Group Visit Ready | Stunning Home w/ Rooftop Deck
Excellent stay for nearby Northwestern graduation - plenty of beds for all (note: tall people will want to stay on first floor, but basement is well-finished), plenty of hot water for morning rush, easy check-out instructions and super-responsive hosts. All in all, a perfect choice for our extended family weekend!

Beautiful home with amazing Lake Michigan views
Really enjoyed the spacious location with views of the water and a well supplied kitchen (you don't see that often, all the tools ready to go and a beautiful space to cook in!) The four of us had fun and were comfortable the entire stay, great place!

Pool Table, Grill & Patio | LCP Collection
Stayed for two days, was fantastic! had a fire in the pit outside, place was clean and exactly as described. host was quick to respond to any questions or problems.
Private house rentals

The River House Sauna/Kayaks/Hot Tub/Fire Pit
Our group of eight were very comfortable in the home. The peaceful river views and outdoor amenities were much appreciated.

Luxe-Haus of Love—The 1938 Cape Cod |Heated FLRS |
Words can’t describe how beautiful and clean the property and neighborhood is! The house is very spacious and modern. The basement is new, has a big room and bathroom with shower. The masters bedroom has a living room and GORGEOUS bathroom! The host provided cleaning supplies and even personal bathroom supplies for men and woman. The host was very nice and friendly 🥰 We had an incident with our previous AIRBNB and we had to rent this one last minute- The host responded at 1am letting us checked in at 1am. If you plan on staying here, please take care of it lol It’s such a lovely house! 100% Recommend!

Wilmette "Treetops" Getaway
We loved this place for a college graduation weekend! Great neighborhood and had everything we needed. Nice touches included lots of plush towels and pillows and high quality everyday things such as shampoo and conditioner, coffee, eye masks, and super plush toilet paper. Great outdoor space too and very responsive hosts.

Big house in the BEST Location!
The house is lovely! Better than the pictures, just as all of the reviews say. The showers are incredible. The master bathroom is a dream. We had everything we needed & more. We don’t have a single complaint. We definitely plan on booking here again.

Steps from the beach and a mile from National Park
Simply beautiful! My daughter ( 7 year old) and my goddaughter ( 5 year old) enjoyed themselves! We loved the layout, beautiful scenery, spacious rooms, the updated amenities, the spa bathtub and the outdoor patio swing is amazing! This house is somewhere you can relax and rewind, enjoy yourself and feel safe at! Angie, is the best! I recommend you stay at Angie’s beach house! You will love this house!!!!!!

Mid-Century Modern Dream Getaway
This was a beautiful house and a beautiful location. My family had a great time exploring the rooms and enjoying the views out the many windows. Lovely trees and lawn space. The design elements of the house were so fun, this felt like a house I would tour - it was cool to stay in!

Pristine - 3 Beds, 1.5 Ba!
10/10. Would definitely stay here again!

Unique and Historic Lustron Home
We had a great stay! The place was clean, cozy, and had everything we needed. The area was quiet and convenient, and check-in was super easy. Would definitely recommend to anyone looking for a comfortable and well-located stay!
Quick stats about house rentals in Highland Park
Total rentals
30 properties
Nightly prices starting at
₹3,462 before taxes and fees
Total number of reviews
1.4K 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
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Alpine Valley Resort
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Geneva National Resort & Club
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- The 606
- The Beverly Country Club