
Holiday rentals in Port Barrington
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Top-rated holiday rentals in Port Barrington
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Port Barrington

Hut in Trout Valley
4.76 out of 5 average rating, 17 reviewsAmazing Horse Country 1 Bedroom Quonset Hut
SherylRating, 5 stars1 month ago
OMG!!! This place is amazing! 2 large closets (w/hangers) and tons of drawer space in the bedroom! Fully furnished kitchen and a huge living area. The bathroom had big, fluffy towels and the shower was refreshing! We spent lots of time sitting on the deck and watching the horses. The house was so clean and as many have mentioned, the historical books about Cary & Trout Valley were very nice. We didn’t need the host for anything - but I feel confident that he would have been helpful if you needed something. Trout Valley is a dream. We visited in May so the trees were green and the waterfalls into the ponds were flowing nicely. My husband said he would love to buy this place…should they ever decide to sell. Such a wonderful weekend - Thank You!!

Place to stay in Racine
4.86 out of 5 average rating, 721 reviewsWisconsin Treehouse Getaway!
NancyRating, 5 starstoday
Amazing cozy place! We spent our honeymoon here and there were lots of great restaurants to eat from. Close by the beach and had a lovely beach day. Check out my TikTok under nancyluzarroyo for more inside footage of the place!

Home in Fox Lake
New place to stayCozy Modern Lake House
AllenRating, 5 stars2 weeks ago
Everything was great. Easy to get to, 30 walk down the street to a shared use spot on the lakeshore. Was nice and quiet during our stay. Thanks again
Guest favourite

Apartment in Crystal Lake
4.88 out of 5 average rating, 192 reviewsCrystal Lake newly updated, walk to beach
SusanRating, 5 stars1 month ago
Staying here felt like we were very much in our own home. It was easy to be comfortable here and there were lots of unexpected conveniences like seasonings and a wide variety of utensils, dishes, and cookware. I recommend a 10/10 and will definitely ask to stay again when we’re in the area.
Guest favourite

Home in Richmond
4.95 out of 5 average rating, 184 reviewsTheGlassCabin @ HackmatackRetreat
ChristineRating, 5 stars1 day ago
From arrival to departure this property delivered, beautiful & peaceful with gorgeous windows that invite the views inside. A charming pond with kayaks and loads of fun art & sculptures keep you entertained at every turn. The easy welcome and the proximity to Richmond and Lake Geneva round out a great experience - we will be back!

Home in Fox River Grove
4.72 out of 5 average rating, 36 reviewsFox River Grove Home: Pets Welcome!
CarlosRating, 5 stars3 months ago
We had a great stay! The house was super clean and the host was very communicative and friendly. The house was perfect for us and Perla was so thoughtful with the amenities she set out for my baby! Can’t wait to stay again!
Top guest favourite

Home in Wauconda
5 out of 5 average rating, 14 reviewsSpacious 4BR Lake House | Steps to Dining & Beach
SergeRating, 5 stars2 weeks ago
The house is clean, light and spacious. The kitchen is roomy and well equipped. The location is also agreeable: a secluded cul-de-sac, right next to the lake, two minutes' walk to Lindy's lakeside restaurant (a solid alternative to home cooking).
Guest favourite

Home in Algonquin
4.89 out of 5 average rating, 47 reviewsOn the Fox River Front/Sauna/Hot Tub/Kayaks/Grills
SanjayRating, 5 stars3 days ago
Phenomenal house. My group of 12 was able to stay in both units of the house and it was a ton of space. Everything was extremely clean with modern finishes, comfy beds. The house was fully stocked with everything one would need including beach towels, kitchen equipment, firewood. There were even amenities added after we booked including in a sauna in the backyard. The backyard is the best part with a huge dining table new and spacious grill setup, large fire pit area, hot tub, and sauna. The surrounding area was beautiful and highly recommend 3 oaks recreation area for a beach, water obstacle course, and beach volleyball. Can not recommend this place enough.
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Six Flags Great America
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Alpine Valley Resort
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Geneva National Resort & Club
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- The 606
- The Beverly Country Club