House vacation rentals in Highland Park

Find and book unique houses on Airbnb

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Popular amenities for Highland Park house rentals

House rentals with a pool

Guest favourite
Home in Lake Geneva
5 out of 5 average rating, 10 reviews

Elssys Ranch 80 Acre Lake Geneva Retreat

ShayneRating, 5 stars1 week ago
Nick was very responsive to any need that arose and took care of things quickly. Great host and very friendly, would absolutely recommend.
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.
Top guest favourite
Home in Bloomingdale
4.94 out of 5 average rating, 48 reviews

Whole House With Hot Tub And Spacious Bedrooms

KarinaRating, 5 stars4 weeks 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
Top guest favourite
Home in Woodstock
4.89 out of 5 average rating, 61 reviews

Grand 1800s Victorian Gem: Updated/by Downtown

AmandaRating, 5 stars1 week ago
My friends and I had a wonderful stay at Deirdre’s home! It’s a gorgeous property with lots of charm and space, and so many great amenities (theater room, claw foot bathtub, Sonos speakers, ample parking, etc.). Deirdre was also very responsive throughout the process and even helped us with a more flexible checkout time. Absolutely recommend visiting her home, we’re already wishing for another trip!
Superhost
Home in Miller
4.83 out of 5 average rating, 36 reviews

Entire House With Pool - Backyard Beach Getaway

CrystalRating, 5 stars5 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 Lake Geneva
5 out of 5 average rating, 5 reviews

Oasis on Oak | Private In-Ground Pool | Hot Tub

DeborahRating, 5 stars10 months ago
It was a beautiful, restful setting for our family to celebrate my wife’s birthday. Thank you for providing a great place for us to meet!
Superhost
Home in Lincoln Park
4.87 out of 5 average rating, 53 reviews

Luxury Loft with Private Pool and Movie Theater

Varun Rating, 5 stars8 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, 137 reviews

Bayless Dune Lodge at West Beach - Indiana Dunes!

KevinRating, 5 stars2 weeks ago
We had a great weekend getaway from Chicago and it was less than an hour (without traffic) away! Peaceful, quiet, near the beach. Cullen was an awesome host!

Weekly house rentals

Superhost
Home in Round Lake Beach
4.82 out of 5 average rating, 125 reviews

Modern 3 bedroom house, quiet residential street.

WilliamRating, 5 stars2 weeks ago
Nice and cozy. Few minutes away from everything you need, and a 5 minute walk from the lake.
Guest favourite
Home in Roscoe Village
4.92 out of 5 average rating, 282 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

MontiraRating, 5 stars2 weeks ago
2nd time staying at Sharleen’s place—wonderful experience! We like location, friendly and quiet neighborhood, walkable to restaurants. We would recommend to guests looking for a space in Roscoe. 🙂
Top guest favourite
Home in Lake View
4.93 out of 5 average rating, 153 reviews

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

JulietRating, 5 stars6 months ago
Lovely place in a good location.
Top guest favourite
Home in Twin Lakes
5 out of 5 average rating, 32 reviews

Beautiful Twin Lakes home + lovely private setting

AmyRating, 5 stars3 months ago
This stay provided a relaxing and quiet atmosphere. Perfect space and amenities. Maria provided perfect communication and the location was safe and clean. The bedrooms are spacious and comfortable. The downstairs bedroom has an ensuite bathroom while the two bedrooms upstairs share a bathroom. The bathrooms has great amenities and are spacious as well. The kitchen was clean and had anything you could want or need to make a meal. Maria even thought of some other items like Tupperware and parchment paper. The coffee maker was serviceable. The gift basket was truly indulgent and appreciated. The big sofa was comfy and the tvs are the perfect size with any app you may want. While it was cold outside and I didn't get to enjoy the property, it was certainly still beautiful and lovely to enjoy my coffee and watch the snow in the mornings. I highly recommend this Airbnb. Thank you for letting me staying.
Guest favourite
Home in Waukegan
4.81 out of 5 average rating, 247 reviews

Modern home. Near naval base, Six flags and Casino

KeiryRating, 5 stars3 weeks ago
Nice home, rooms were pretty spacious & good for a family stay. Very peaceful!
Superhost
Home in Twin Lakes
4.84 out of 5 average rating, 152 reviews

Private Lake House, with boat option- 14 beds

CarrieRating, 5 stars1 week ago
This house was perfect for our group! There were plenty of beds for all of us, plenty of extra air mattresses to use and tons of extra linens and towels. The rooms were clean and cozy. The living space was warm and inviting and the kitchen was STOCKED with anything we could have needed! The house was clean and ready for us - even a little earlier than planned! Jeff was a fabulous host to work with. From the day we reached out to inquire about the property, he was responsive, friendly and helpful. The highlight of our weekend was spending the beautiful sunny day outside - looking at the water and relaxing with friends. There was plenty of comfortable seating outside - including a fire pit that we used to make s’mores one evening. Some of us took out the canoe and enjoyed our time on the beautiful lake. Our group lives about 50 mins away and we truly felt like we were far from home on vacation! I highly recommend this property and would definitely work with Jeff again in the future!
Top guest favourite
Home in Salem
4.92 out of 5 average rating, 26 reviews

Hideaway at the Ponderosa- 3bd 1Ba Country Cottage

KevinRating, 5 stars6 months ago
the host was amazing! very responsive and made check in a breeze. place was great and close to restaurants and shopping.
Guest favourite
Home in Third Lake
4.93 out of 5 average rating, 14 reviews

Home for flexible term rental

AlanaRating, 5 stars2 weeks ago
This place was perfect for my husband, our ten year old and my mother and I. Plenty of space and privacy for my mother on second floor, and for us on the first floor. Everything was well designed- there was plenty of flexible and very comfortable seating in the living room and bedrooms for hanging out, and also around the dinner table. So much natural light, and free of clutter, yet it felt homey and like someone cared about their space, not just furnished as a rental business. The neighborhood was great for playing pass in the cul de sac, or across st at park and playground, and lovely for walking. Kitchen appliances were primo, and we found everything we needed. Thank you for such an enjoyable stay!

Private house rentals

Guest favourite
Home in Powers Lake
4.78 out of 5 average rating, 64 reviews

Powers Lakehouse Loft

AnthonyRating, 5 stars6 months ago
It was exactly what we were looking for. Very quiet with beautiful views. Being able to sit in the hot tub and take in the sunset was incredible. Any questions we had were answered quickly by this very kind host.
Guest favourite
Home in Antioch
5 out of 5 average rating, 18 reviews

All seasons country house

ChrisRating, 5 stars5 months ago
Agnieszka's place was perfect for our visit with our son as he graduated boot camp. The home had everything we needed. The minimal decorations made it very easy to clean and easy to find all our stuff when we left. The home is beautifully remodeled on the inside. Much respect to the designer. We brought extra toiletries and paper products and dishwasher tabs because we were staying so many days. There was an adequate amount for a simple weekend stay. Plenty of sleeping space for several people. Just remember there is one bathroom. By the way, there is a great Jewel-Osco grocery store close by. We also visited an exceptional museum in Volo. It was perfect for a family, especially the boys! I really enjoyed the short drive to Kenosha, WI to gather stones by Lake Michigan.
Superhost
Home in Bristol
4.86 out of 5 average rating, 49 reviews

Huge Lake Retreat Spa near Lake Geneva, Wilmot

AngelikaRating, 5 stars2 weeks ago
I can’t say enough wonderful things about this lake house! From the moment we arrived, everything surpassed our expectations. The home was spotless, beautifully decorated, and equipped with everything we needed for a relaxing and memorable stay. Waking up to the view of the lake every morning was absolutely magical. The hosts were incredibly thoughtful and responsive, providing clear instructions and delightful little touches throughout the home that made us feel welcome and comfortable. I highly recommend this place to anyone looking for a lovely lakeside retreat!
Superhost
Home in Glendale Heights
4.8 out of 5 average rating, 44 reviews

Spacious 4 Bed Room suburban home

BrandeeRating, 5 stars20 months ago
Uthuman’s was a great place to stay! It was cozy! There were plenty of towels available. The beds were comfy and everything was clean. I had quick responses to any questions I had. I would recommend staying here!
Superhost
Home in Naperville
4.87 out of 5 average rating, 127 reviews

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

NathanRating, 5 stars1 month ago
It was a comfortable stay. Tons to do in the area. Can’t go wrong!
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.
Superhost
Home in Homer Glen
5 out of 5 average rating, 3 reviews

4 bedroom home rental in quiet neighborhood

LoriRating, 5 stars71 months ago
Quiet neighborhood, spacious and comfortable home. The yard is inviting and a great entertaining space! Very kind hosts.
Top guest favourite
Home in Itasca
5 out of 5 average rating, 52 reviews

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

JanetRating, 5 stars1 week ago
This was our second time staying at Jehu's home in Itasca, IL. We have family and friends nearby so the location is perfect. The beds are comfortable, and the house is very clean. Having bottled water, coffee, a variety of beverages and snacks at our disposal was a plus. Jehu was very responsive to any questions we had. We would definitely book this property again for our next visit to the Chicagoland area.

Quick stats about house rentals in Highland Park

  • Total rentals

    30 properties

  • Nightly prices starting at

    $56 CAD 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

Destinations to explore

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  3. Illinois
  4. Lake County
  5. Highland Park
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