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Compare 208 Vacation Homes in Highland with updated reviews, rates, and availability.

"Could not be more thankful for her prompt replies and accommodations."

"The property has lots of space and a game room, ideal for a fun getaway with a large group. Close to bus stops and Metra station (different from metro station, we learned this the hard way). Walking distance from the U of Chicago."

"The property was very nice and spacious. The location was great and the parking in the back was amazing. We felt safe and happy our whole stay. "

"Overall great experience! Great home, I love the decor of the entire home. And I will definitely recommend to others and will book again "

"We recently rented this home for our church's women's fall spiritual retreat. This stay for our group of 21 ladies was more than we expected. We chose this home for its size, proximity to the shore, and great accommodations. Upon our arrival we were pleasantly surprised to find the house had been recently updated. It was absolutely beautiful...bright, serene, and peaceful! The cleanliness of the home was great! The attention to detail was appreciated. I love a well stocked kitchen and this...

"I stayed in this home for two nights. It was cold as ever. The heat did not work at all, no matter how high I turned it up and I couldn’t even heat up my food in the microwave because that didn’t work either. My food was not getting warm no matter how long I put it on in the microwave me and my company was cold For both nights."

Matteson Vacation Rental | 4BR | 2.5BA | 1,800 Sq Ft | Stairs Required

"We really love the home and the setup."

"Listed as private home , once you get there and read the house rules it states shared refrigerator with owner. Owner comes in while you are gone and turns off all lights and the Ac, even goes into your locked room to turn off ac."

"Very clean in a safe neighborhood. I would stay here again"

AED 802 total

includes taxes & fees

24 Dec - 25 Dec

"The pictures don’t lie! Very nice clean house! Updated kitchen and the best backyard!! We came to see the beach and this place was the perfect vibe! Would definitely recommend! There’s a nice little adults only club down the road too! Very pleased! 5 + star!! "

The Pool Barn Camper sits in the drive of our Pool Barn

"Would reserve this again wonderful host"

AED 407 total

includes taxes & fees

23 Dec - 24 Dec

"We affectionately refer to this property as the Christmas house! The antique sleigh is a big hit with our grandchildren. We have stayed here multiple times and it’s always our first choice when we’re in the area. The house is very spacious, clean and homey. We have a large family and have plenty of room to spread out. The hosts are absolutely wonderful! Highly recommend!"

AED 1,107 total

includes taxes & fees

30 Dec - 31 Dec

"Thoroughly enjoyed our stay at this lovely home. It was clean, comfortable, and well equipped. The beds in particular made for the best sleep I have had in a long time. "

"A very nice experience "

"We were in Homewood for a wedding and this was a perfect location. Besides its proximity to the wedding venue, we walked to the train station for a day in the city. The house is exactly as listed. It was very clean, organized and comfortable. Everything we needed was supplied. My husband especially liked the TVs. 😊 Since we were there on Halloween, we had the added bonus of seeing a truly family-oriented neighborhood in action. Lots of happy trick-or-treaters showed up accompanied by lots of...

"Overall it was a great experience and I’ll be coming back sooner"

"…for me. Clean, cozy, close to everything, quiet and well appointed. This was my second stay and I will continue to return for my family holiday visits. Comfy bed with great pillow’s! "

Griffith Vacation Rental | 3BR | 2.5BA | Step-Free Entry | 1,753 Sq Ft

"House was a perfect place for our family (and dog:) to stay for our son’s wedding in Munster. Loved the kitchen area to gather with our family. Snacks, fruit and water upon arrival were a nice bonus. Great communication with host."

"We thoroughly enjoyed our stay at Cedar Sunset on the Lake! The home was extremely clean and provided every necessity that you could ever need! The bed and furnishings were extremely comfortable and by far the best I’ve experienced in a rental property. The lake was right out the back door and we spent a lot of time on the dock while the kids were always in the lake and provided paddle board. The home was also in close proximity to Crown Point, but the town of Cedar Lake offered everything...