Vacation rentals in Oakwood Hills

4.97 out of 5 average rating, 33 reviews

Pet-Friendly Slice of Heaven by Lake Geneva & Como

GinaRating, 5 stars5 days 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

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!

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.

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.

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!

Superhost

Cottage in Antioch

4.83 out of 5 average rating, 169 reviews

#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.

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Other great vacation rentals in Oakwood Hills

Superhost

Home in Kenosha

4.92 out of 5 average rating, 271 reviews

Where Family & Friends Gather to Create & Remember

AliciaRating, 5 stars2 weeks 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, 50 reviews

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

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

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

Apartment in Jefferson Park

4.63 out of 5 average rating, 24 reviews

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars3 weeks ago

Peaceful, felt like home, very spacious and comfortable

4.92 out of 5 average rating, 115 reviews

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!