Vacation rentals in Highland Park

A modern kitchen features sleek cabinetry and stainless-steel appliances, including a large refrigerator and gas stove. A spacious island with seating for four is complemented by pendant lights above. Natural light filters in through a window, illuminating the clean design.

4.97 out of 5 average rating, 33 reviews

Pet-Friendly Slice of Heaven by Lake Geneva & Como

GinaRating, 5 stars1 week 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, 141 reviews

A serene pathway lined with lush greenery features tall trees and blooming flowers. An inviting red chair is positioned in the background. A friendly sign indicating 'KEEP RIGHT' guides guests along the landscaped route toward the cottages.

Bungalow in Lake Geneva

Private Cozy Cottage Lake Geneva, WI

JasonRating, 5 stars4 weeks ago

We loved this place. It was an easy walk down to the water and into town for restaurants. The special touches of a bottle of wine waiting for us, the full basket of continental breakfast options, the gas fireplace, and the jacuzzi made this cozy little cabin feel like a resort. They raised the bar for what you AirBnbs should can. Perfect for a couple getaway.

4.98 out of 5 average rating, 144 reviews

Updated luxury country getaway short walk to lake!

KaitlinRating, 5 stars1 week ago

The house was cozy and clean! I am sensitive to fragrance and appreciated the home not being overly scented! Walkable to the lake and we loved seeing all the deer in the neighborhood. Shari was easy to get in touch with and we were provided with everything we needed during our stay.

4.96 out of 5 average rating, 79 reviews

Huge! Sleeps 12, Perfect getaway for a large group

ElaineRating, 5 stars3 months ago

Beautiful home with ample space for our group of 10! It was our first Christmas without my mother and we decided as a family to spend our holiday somewhere new. The owner of the house made sure we had everything we needed and went over and beyond to make the house look festive! Despite it being winter, there were a lot of things to do. We made use of the beautiful game room, played cards, board games, shot pool and had our daily movie night in one of the two large family rooms. We had such a great experience despite my family’s loss that we are thinking of returning next year!

The exterior of the Clean Slate is characterized by a dark wooden façade and a welcoming front porch. A paved walkway leads to the entrance, flanked by neatly landscaped grass and flower beds. A large tree provides shade, enhancing the outdoor appeal.

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!!!!

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.

A spacious bedroom features a large bed with a light-colored comforter and decorative pillows. Soft lighting is provided by bedside lamps on either side of the bed. A ceiling fan circulates air, and natural light fills the room through a large window with a view.

4.97 out of 5 average rating, 153 reviews

NEW! Cozy Downtown Farmhouse, 5BR 3 BA Sleeps 15!!

MorganRating, 5 stars1 month ago

Highly suggest Brian’s place! Exactly like pictures and perfect for a weekend getaway. Home was beautiful and newly updated! Everything was walkable, perfect location to downtown. We had 14 guests and everyone was comfortable and beyond happy with accommodations! Brian was easy to work with and everything was clear for us. Thanks for a great stay! We will be back.

A well-maintained house features a spacious composite deck, bordered by white railings. Large windows provide natural light to the interior. Lush green grass surrounds the deck, complementing the clear blue sky and leafy trees in the background.

5 out of 5 average rating, 26 reviews

Modern Downtown Lake Geneva Charm - Sleeps 8

Jose & DonnaRating, 5 stars3 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!

0 of 0 items showing

What guests are saying

Cozy Cottage by the Lake! Kayaks! Paddleboard! Wow

5 out of 5 average rating, 5 reviews2 months ago

This cottage was wonderful to stay at! Very cozy! Great to stay at in winter as an indoor getaway and this would be an awesome stay in the summer. I passed up the place at first when I arrived because I didn't think it would be that nice of a place! Rainfall shower was nice and great areas to sit and chill out. I would definitely stay here again!

Home in Salem

What guests are saying

The Harbor House - Amazing!

4.94 out of 5 average rating, 16 reviews6 months ago

I honestly can’t say enough great things about everything - they are such kind, considerate, lovely, beautiful people & their house was amazing!!! Everything top notch, great instructions, great & quick communication. Above & beyond & my family and I are so grateful and thankful. May God continue to bless Karen & Paul bc they are deserving. Thank you!!!!!

Home in Winthrop Harbor

What guests are saying

Lake/Beach Getaway (Remodeled)

4.85 out of 5 average rating, 72 reviews1 month ago

Me and my guests had an amazing time at marks home . His hospitality and attentiveness to his guest was spectacular. Any questions I had, I felt comfortable enough to ask because I knew he would be helpful and answer any questions. His home was beautiful and we extremely enjoy our stay .

Home in Round Lake Beach

1 of 12 pages

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Highland Park vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Highland Park's top sights

Chicago Botanic Garden167 locals recommend

Ravinia Festival West Lot33 locals recommend

Ravinia Festival Box Office14 locals recommend

Northbrook Court11 locals recommend

Jewel-Osco9 locals recommend

Lake-Cook Rd & Turnbull Woods Ct station8 locals recommend

Other great vacation rentals in Highland Park

Superhost

A tranquil view of the lake is captured at sunset, with golden hues reflecting on the water. A torch stands in the foreground, gently illuminating the scene, while trees frame the image along the edge of the deck.

Home in Fox Lake

4.89 out of 5 average rating, 55 reviews

Stunning Lake Views, Huge Deck, Water Fun!

KymRating, 5 stars2 months ago

Absolutely Loved our stay!! There aren't enough good things to say about the view, location & beautiful house. So fun! There's a pool table, air hockey & 2 free standing video games. Spent every sunset in the Lakeview room😍 Just gorgeous beyond words! Did i mention the Bald Eagle that hangs out in the tree right outside the Lakeview bedroom? Incredible! the lake doesn't freeze over in one spot in front of the lakeview window, saw all the big birds of prey hunt. It was definitely wildlife at its finest. The owners are Very responsive & told us to be on the look out for the eagle! Fantastic time! Loved Loved Loved it & already reserved for our Wedding weekend❤️

5 out of 5 average rating, 51 reviews

A spacious living area features comfortable seating arranged around a central coffee table. A wall-mounted TV is visible above a white fireplace. Soft lighting is provided by a contemporary chandelier, and large windows are dressed with light curtains, enhancing the room's bright ambiance.

Home in Schaumburg

Great location-King beds-Kids playroom

AdamRating, 5 stars2 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.

5 out of 5 average rating, 5 reviews

A modern living space is presented with a white sofa and two accent chairs, arranged around a minimalist coffee table. A dining area is visible in the background, featuring a gold and glass table set with decorative items. Natural light filters in through large windows.

Home in Chicago

Birthday?Anniversary?Showers?3500 sq ft, sleeps 16

ArissRating, 5 stars1 week ago

Vince’s place was amazing, it was such a good location, easy to drive to anywhere in Chicago. Vince was very easy to contact and was responsive within minutes. He made our stay very comfortable. The house was amazing and there was a lot of space, and there was a lot of amenities available for use, for example kitchen utensils and shower amenities. Overall this stay was amazing and I would book this again if I came back in the future

4.86 out of 5 average rating, 42 reviews

A cozy living area is presented, featuring a stone fireplace as a focal point. Two armchairs are positioned around a coffee table, with decor additions providing a touch of greenery. Natural light enters through nearby windows, illuminating the light-colored walls and hardwood floors.

Apartment in Albany Park

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars2 months ago

Wonderful stay as always, thank you so much!

Superhost

A modern kitchen is equipped with sleek stainless steel appliances, including a microwave and dishwasher. Light countertops complement dark cabinetry, while a small countertop with two barstools provides a casual dining option. Natural light filters in through a window near the door.

Apartment in Jefferson Park

4.63 out of 5 average rating, 24 reviews

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars4 weeks ago

Peaceful, felt like home, very spacious and comfortable

4.92 out of 5 average rating, 115 reviews

The image showcases a sandy beach area beside a calm water channel. Colorful kayaks and a canoe are positioned along the shoreline. A spacious green lawn is framed by large trees, with blue lawn chairs and a hammock visible in the background.

Home in Antioch

Entertain on The Chain! water sports and sauna.

JoshuaRating, 5 stars1 week ago

Tucked along the quiet northern edge of Antioch, this house doesn’t just offer a place to stay - it gives you something to feel. Vaulted ceilings, custom barnwood beds, and raw concrete countertops set the tone: warm, solid, and built with intent. The private beach isn’t flashy - it’s better. Soft sand, still water, and no reason to rush. Grill outside, gather at the big family-style table, then sweat it all out in the sauna that feels like it was made to erase stress. The beds hit the sweet spot between firm and forgiving. Every corner of the place feels curated without being pretentious. Jewel is just up the road if you need supplies, but you’ll quickly forget the outside world exists. And Waylon? The kind of host you rarely get - quick to respond, genuinely helpful, and fully dialed in without hovering. This isn’t just a weekend rental - it’s the kind of place that makes you rethink how you spend your time off. You’ll leave better than you arrived.

4.92 out of 5 average rating, 344 reviews

Cabin in Trevor

Living the Lakehouse Dream

AshlynnRating, 5 stars1 week ago

This was the cabin of our dreams! My friends and I came here for a girls weekend and fell in love! The owners provided firewood for us and left detailed instructions about all parts of the property. The pictures don’t do this place justice - such a beautiful area and cozily decorated cabin! 10/10 would love to come back!