
Holiday rentals with a kayak in McHenry County
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Top-rated rentals with kayak in McHenry County
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House rentals with a kayak

Lakefront Paradise
We had a great weekend. Spacious and clean and we really enjoyed our time!

Walk 2 lake, HOT TUB, pool table, bikes & kayaks
Audrey was an amazing host & her house was cozy! The house itself had plenty of things to do inside & outside of it but was also in the center of many different places to visit. Furthest we drove to go somewhere was 15 minutes. Would 10/10 recommend Audrey as a host & her home as a place to stay!

Lakefront, beautiful views, spacious and private.
We had a great time celebrating our daughters graduation from college! It was nice to have a space large enough for our entire family together, to relax and enjoy the outdoor outdoors! George was a very responsive host and we thoroughly enjoyed the fire pit a couple of nights just sitting around and enjoying our time together!

Entertain on The Chain! water sports and sauna.
me and my family had an amazing time felt super comfortable and cozy. pet friendly everything I needed was at hand and host was kind answered everything I needed instantly. Susan was clean and worth every penny.

Corner Lakefront Property
This house is simply wonderful. It has the best beachy cottage summer vibes! The location is also great very private for being somewhat close to the city, and very close to Six Flags. We especially loved mornings on the deck and taking the kayaks out on the lake. Can't wait to stay again!

Riverfront rental
Lucy was a great host. She offered an early check in which helped and communicated with us which I appreciated. Would stay with her again. Thank you!!

Beautiful Lakehouse sleeps 12 Boat/Pets/HotTub/Ski
Will was very responsive and his place was very relaxing and cozy. My family had a great time!

Our Sweet Retreat is waiting for you
We had a fantastic stay! The place was clean, comfortable, and exactly as described. The host was friendly and responsive, and everything we needed was provided. The location near Lake Como and Lake Geneva was perfect—close to everything but still quiet and peaceful. Would definitely stay here again and highly recommend it to anyone visiting the area!
Cottage rentals with a kayak

Cozy Cottage-blocks from lake-garage arcade room
The house was perfect! Last minute some friends and I decided to do a quick getaway while on spring break and Toninas house was more than exceptional! The garage was so cool with all the games and sitting area, the house is easily walkable from the lake, and Tonina responded to me with great suggestions on where to eat and other activities to do for our specific age group (21-25) and some other family friendly suggestions. She is a great host and has a lot of knowledge of the area! We’re already talking about plans to book for the summer when the lake is open!

Great getaway in Lily Lake Near Country Thunder
liked it

Twin Lakes Bungalow
My husband and I were looking for a weekend escape from Chicago and we really lucked out with this space!! We have a large dog and wanted a home with a private fenced in yard and he absolutely loved it here. The yard was massive, and the house was quaint and private. Easy walking to restaurants, bars and the lake! Jess was a beyond amazing hostess, and was extremely responsive and friendly. She left us a bottle of wine which was a HUGE plus :) we spent a majority of our time in the backyard with our dog (it was a vacation for him), but we also went to a Sand Bar, George’s, Manny’s and the ice cream shop!! We loved it all and will be back!!

#5 Tiny Lake Cottage at Cypress Resort & Marine
The Cabin was super cute and just as described. Every time I reached out with a question or request, Amanda responded promptly and helpfully. Would definitely book again.

The Lily Pad at Lake Wandawega
This stay is amazing for quiet mornings with coffee on the deck. It’s right on the water with the ability to kayak and paddle board. The amenities are amazing and it’s the perfect place for a couples getaway weekend. Close distance for day trips to Lake Geneva or concerts at Alpine Valley!

Connie's Cottage on the Lake.
Absolutely fantastic property and fantastic host. Very responsive, understanding, flexible, friendly! I booked the cottage to celebrate my mother's birthday and we had the absolute best time. In terms of amenities, the house had everything needed to cook our feasts ; plenty of cutlery, cups, glasses, pans, bowls , spices! Great dishwasher too. Although our trip fell on a windy few days we still had plenty to do to keep ourselves entertained from the karaoke microphones and games to flying kites with our kid, making s'mores at the fire pit and playing air hockey. Well worth the money and highly recommend to anyone that wants a peaceful getaway. Thank you Connie!

Key House at Petite Lake Resort, #4
Amanda sent great information and instructions prior to checking in and was helpful and communicative. Beautiful place, clean, comfortable. Used the fire pit, which was enjoyable. Lots to do outdoors.

Lakefront Cottage Spectacular Sunsets Boat Rental
Great location! Directly on the water. Great relaxing location. We had to cut our stay short there due to circumstances out of our control but the place is safe, friendly and exactly as described. Great for sun bathing. The rental has plenty of places to sleep. The beds were amazing, I was going to take a pic of mattress to buy for myself. The lake is beautiful, great to kayak, or float around. Because we had to abruptly leave I didn't get to clean and organize the place back to how it was. I don't blame the host if upset for those reasons. I will stay again. The local restaurants are not open during the weekdays for the most part. Lake Geneva is 20 minutes from the location for boutiques and restaurant. If you are looking to getaway and relax with a great lake view this is the place for you! The host was amazing as well!
Cabin rentals with a kayak

Go Camp Como! Walk to Lake Geneva's Como Lake!
Jeanne’s place was in a nice location about a 10 minute drive to everything in Lake Geneva. Very spacious. The house does sleep 12 but if your party isn’t comfortable sleeping in bunk beds, it might not be for you! it worked great for our group and Jeanne was very responsive when we had questions about the air conditioning! Overall, i would definitely stay again!

Hunter Cabin on Petite Lake, Ol Pine Lodge Cabins
Will definitely be recommending to any family or friends that want a waterfront getaway! Robyn and Tim were fantastic hosts and welcoming from the very second we stepped out of the car. The location of the property makes you feel secluded but also part of the lake life experience of the "Chain" all at the same time. Friends nearby had no trouble picking us up from the private pier for a boat ride, and Robyn also offered up use of the kayaks right away. The only thing I would change was how much time we were able to stay at the cabins and utilize the fire pit/beach/deck/etc. Need a stay in the future!

The Fox Den / Midcentury A-frame
We had an amazing stay and highly recommend this property!

Spacious 2BR Cabin@The Lake-Heim
The cabin was really clean and cozy and it’s location right beside the lake was perfect. Loved that they had kayaks and paddleboards, a private dock, and a firepit. The outdoor area felt private and peaceful. Easy check in and check out.

Enjoy a Getaway @ The Lake-Heim by Chain-O-Lakes
We were looking for a quiet place to retreat and this was exactly what we needed. The cabin was cute and comfy, the area felt safe and was super close to the water, and the view was amazing. We would totally recommend and love to come back and stay again! Everything we needed was right there!

Living the Lakehouse Dream
Had a great time here with a group of friends. Loved having our dogs here with us, house was well-equipped for us to cook meals, enjoy the hot tub, paddle on the lake, play lots of volleyball, and relax indoors & outdoors.

ELK Cabin on Petite Lake, Ol Pine Lodge Cabins
Tim & Robin's place was wonderful! The cottage (#1) was exactly like the pictures and was very clean. Tim & Robin live on-site and we were greeted upon arrival. Through the weekend we had several passing conversations that were very pleasant. They had lots of solid recommendations and made sure we were comfortable. The property itself was simply dreamy! There was a nice beach area as well as an elevated deck overlooking the lake. We would definitely recommend renting here and plan on returning at some point in the future.

Large Lake Cabin – EV Charger, Peloton, Ski Nearby
We had an amazing stay at Marina’s Airbnb! We had 11 guests, and there was more than enough space for everyone to sleep, shower, eat, and relax comfortably. The home was beautiful, super cozy, and had everything we needed—including a great patio perfect for grilling and hanging out. Marina was an incredible host and answered all of my questions quickly and kindly. We loved our stay and would absolutely come back!
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Six Flags Great America
- Humboldt Park
- 875 North Michigan Avenue
- Lincoln Park
- Alpine Valley Resort
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Willis Tower
- Geneva National Resort & Club
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- The 606
- Racine North Beach
- Grand Geneva Resort & Spa
- Richard Bong State Recreation Area
- Moraine Hills State Park
- Chicago Cultural Center