Holiday rentals in Highland Park

4.94 out of 5 average rating, 34 reviews

Pet-Friendly Slice of Heaven by Lake Geneva & Como

GinaRating, 5 stars2 weeks ago

We truly enjoyed our stay at Joe and Nadine's place! The house was beautiful, spotless, and relaxing. It was the perfect place to unwind. The location was close to restaurants and activities around Lake Geneva, Lake Como, and surrounding towns such as Delavan and Elkhorn. Joe and Nadine were wonderful hosts- providing ideas for things to do/see in the area, as well as providing great restaurant recommendations. They were also super quick to respond and really seemed to want to make sure we enjoyed our stay. If you're looking for a relaxing reprieve and a sparkling clean space with all you need to feel at home, look no further!

4.97 out of 5 average rating, 144 reviews

Bungalow in Lake Geneva

Private Cozy Cottage Lake Geneva, WI

StefanyRating, 5 stars1 week ago

We love staying at Seven Oaks and have many times. I particularly enjoy the soaker tub and we appreciate the cheese tray, drinks, and breakfast foods. It makes it so much more enjoyable to get away and not have to think about running out to get food. We stay as often as we can get away. Such a great place!

4.96 out of 5 average rating, 81 reviews

Huge! Sleeps 12, Perfect getaway for a large group

RachelRating, 5 stars1 week ago

This home was incredible for a weekend away with girlfriends. We loved the views of lake como m, the proximity to downtown lake Geneva, and how well stocked the house was with all the essentials and more (especially in the kitchen!). Only regret was not making our stay a full week long trip!

4.94 out of 5 average rating, 34 reviews

The Clean Slate, Walk to down town, pet friendly

DavidRating, 5 stars6 months ago

Beautiful house and so comfortable inside and out. My bestie and my dog were in Lake Geneva for the weekend and very much enjoyed The Clean Slate. The weather was perfect! The house was just as described. Highly recommended!!!!

5 out of 5 average rating, 5 reviews

Home in Twin Lakes

Rustic Cottage Downtown Twin Lakes

MaryRating, 5 stars2 months ago

We needed an extended rental due to a move and Brian’s place was perfect. The house was clean and updated and met all our needs. Brian communicated perfectly throughout the stay. Would highly recommend to anyone wanting to stay in the area.

4.95 out of 5 average rating, 44 reviews

1 block to the Lake, then 2 blocks to Downtown

PeteRating, 5 stars1 month ago

If every host could be like Ryan and Angela - this app would be a much better place. They were extraordinarily communicative, attentive and eager to ensure all needs were met. The house was perfect (with a lot of character) - and is a couple of blocks away from the lake and lake trail. Also very close to downtown (for those who don’t mind the walk). Overall, this house is perfect for families looking to create long lasting memories and is managed by hosts that will go out of their way to make it so.

5 out of 5 average rating, 27 reviews

Modern Downtown Lake Geneva Charm - Sleeps 8

Jose & DonnaRating, 5 stars4 months ago

We had a fantastic stay! The location was incredibly convenient, just a short distance from great restaurants and our ski/snowboarding resort, which made everything so easy. The place was very well kept, cozy, and had plenty of space—perfect for our small family staying for two nights. The host was wonderful—attentive, helpful, and quick to communicate, which we really appreciated. We couldn’t have asked for a better experience and would definitely stay here again! Highly recommend!

4.87 out of 5 average rating, 126 reviews

Home in Fox Lake

Lakefront Paradise

AnkitRating, 5 stars2 weeks ago

We had an amazing stay. The area is beautiful and Nick is prompt in responding. We had no issues during our stay. If you stay the there definitely try all the local places he’s recommends for drinks/dine and won’t be disappointed. I must add that unlike some Airbnb where they ask the guests to do a whole host of things, this place had very few and reasonable rules that we were happy to comply with.

4.83 out of 5 average rating, 169 reviews

Cottage in Antioch

#1 The Lodge @ The Cottages on Petite Lake

GraceRating, 5 stars1 month ago

The place was stunning, inside and out. The couches were very comfortable. The hot tub was amazing. The view of the lake and beach was phenomenal. The beds were very comfortable. Had a great time staying here and would 10/10 recommend to others looking for a beautiful, relaxing lake house.

Holiday rentals for every style

Get the amount of space that is right for you

Houses

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Hotels

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Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Highland Park holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Highland Park's top sights

Chicago Botanic Garden67 locals recommend

Ravinia Festival Box Office14 locals recommend

Lake-Cook Rd & Turnbull Woods Ct station8 locals recommend

Miramar Bistro3 locals recommend

Rosewood Beach6 locals recommend

Abigail's American Bistro4 locals recommend

Other great holiday rentals in Highland Park

4.92 out of 5 average rating, 272 reviews

Home in Kenosha

Where Family & Friends Gather to Create & Remember

AliciaRating, 5 stars1 month ago

We had an amazing stay! The place is beautiful & looked exactly like the pictures. We would highly recommend staying here.

5 out of 5 average rating, 51 reviews

Home in Schaumburg

Great location-King beds-Kids playroom

AdamRating, 5 stars4 weeks ago

Ninna's place was fantastic! It was exactly as described, and the process was proactive. Ninna communicated very well and anticipated questions we may have. We had friends from the area join us for dinner, and Ninna was accommodating of that request. Her place was perfect, with everything we may need during our stay. The kitchen was stocked with all the things we needed, and the coffee nook was a nice touch! The kids enjoyed the little playroom upstairs, and the mattresses were very comfortable.

4.86 out of 5 average rating, 42 reviews

Flat in Albany Park

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars2 months ago

Wonderful stay as always, thank you so much!

4.63 out of 5 average rating, 24 reviews

Flat in Jefferson Park

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars1 month ago

Peaceful, felt like home, very spacious and comfortable

4.92 out of 5 average rating, 346 reviews

Cabin in Trevor

Living the Lakehouse Dream

Andrea NicoleRating, 5 stars1 week ago

We really enjoyed our stay and all the amenities your place has to offer. Thank you!

4.87 out of 5 average rating, 15 reviews

Home in Richton Park

Home away from home

TamaraRating, 5 stars2 days ago

The house was amazing—clean, spacious, and perfect for both rooming and hosting a baby shower. The kitchen was beautiful, and the huge backyard was a big plus! Delbert was very responsive and made sure everything went smoothly. The location was also great—close to local stores and the expressway, which made getting back and forth super easy. I’ll definitely book again!

5 out of 5 average rating, 25 reviews

Home in Lombard

Spacious Home in Chicago Suburbs

JenniferRating, 5 stars3 weeks ago

It was great! The house was lovely and looked newly renovated. It was much roomier than I expected. The beds were very comfortable.