
Family-friendly holiday rentals in McHenry
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Top-rated family-friendly rentals in McHenry
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Popular amenities for McHenry family-friendly rentals
Family-friendly home rentals with a hot tub

Lakeside Getaway
Christine’s place was the perfect get-away for a family vacation close to home. The lake was beautiful and the place was spotless and inviting. It felt like you walked in to your own home. It’s close to places to eat and there is even a community space just a few houses down that is lively if the weather is nice. I’m hoping to come back again!

Hot tub getaway Extra Large capacity home
Such a great home for our small staff retreat! Will definitely check availability for this home for future needs! Joe and Shelly are great hosts!!

Lux Urban 3BR/3BA Duplex + Parking!
Great stay! Thanks for making it so easy. Big space for lots of family to be together and have space.

#1 Old Lake House at Cypress Resort & Marine
Amanda is the best host I’ve ever had, she is so friendly and responsive. Her kitchen was fully equipped, she gave us the option of having firewood delivered, the place is absolutely beautiful, you walk down some stairs to get to the beach. A group of 8 moms went there for a weekend getaway and it was exactly what we needed. Thank you!

Restored Victorian w Hottub , 1block to shops
This house looks like it does in the photos. It is an easy walk to downtown in a safe area. Had a great stay overall!

Bright and Beautiful Penthouse - Close to the lake
We had a great stay at Delphine's place in Uptown. The location is excellent, being on a tree-lined street, but very close to the Red Line, the Broadway bus, Andersonville, Little Asia, grocery stores and more. As we had a little kid, being right on top of the little park downstairs was also very convenient. On the flipside, it can get noisy in the summer with lots of kids/playgroups coming there, but as parents, we didn't mind. Delphine herself was very quick to respond via Whatsapp to all our queries before and during our stay. One thing to keep in mind at her place is that you are very much living in their home. If you are looking for an apartment that is only intended for guests, this is not it. While it is plenty big as a 2BR/2BA, it is full of stuff, furniture, photos, books, toys, etc. They have made a very nice office space in the main living area, but the drawback is that the living area is now very cramped. The main bedroom has 2 queen size beds in it, which is a bit weird, so we just ended up using one bed to keep our clothes on. The other bedroom with bunk beds is excellent for kids and more spacious. So overall, a great place and a great stay, and especially good if you are a couple with 1 or 2 kids. Just a bit cramped and crowded with stuff. We stayed for 2 weeks.

The Retreat on Lake Michigan 6 bd/4bth 4000 sq ft
We had a wonderful stay at Daniel’s place! The house is beautiful and the view is stunning. It was really clean and felt very welcoming. We traveled with grandparents and kids and everyone found something to enjoy. The pool table was a huge hit, as was the badminton set and the multiple outdoor seating areas. This one is highly recommended!

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!
Family- and pet-friendly home rentals

Roscoe Village One Bed Lux Apartment Near Wrigley
I would highly recommend Dennis' place. It was super clean. Had all the amenities you may want. Close to a lot of places yet quiet. We felt totally safe and loved the balcony.

Sunny Logan Square Artists' home
We loved our stay at Kyle’s place - it was decorated SO cute (I went with two girlfriends and I’m pretty sure we all squealed with joy when we first opened the door). The location was perfect - just a quick walk to all the shops and restaurants Logan Square had to offer - and to public transportation (which we used the whole time in Chicago). The neighborhood was very peaceful and quiet; we all felt very safe. When I come back to Chicago, I will absolutely be staying here again. Thanks for sharing your space with us, Kyle! We loved it! (Side note: you gave me so many ideas for house decor, your style is impeccable!)

Private 3rd Floor Apartment
Very comfy apartment in a great neighborhood. We were in town for a baseball game and it’s a terrific place for that, just about a 20-minute walk to Wrigley Field. The only thing to be concerned about is the stairs: there are two flights to get into the apartment and they’re fairly steep and small, so if you have mobility issues that would be a concern. I don’t and had no problem. Karen is a lovely host and was very helpful when I was getting into the place and unloading my stuff from my car. There are tons of restaurants and coffee shops in the area, so it’s a great place to explore and hang out.

Andersonville Living
Comfortable, homey place for our group of five. Great back deck for outdoor time. Wonderful neighborhood with lots of shops and restaurants. Good beds.

2nd floor of 1908 brick two-flat in Logan Square
Great host. Would definitely stay again. Good location, convenient subway within a few minutes walking. 12 min to Downtown.

Garden Unit Getaway-Bucktown
great stay, super clean apartment, great communication on keith’s end would definitely stay again. thank you for accommodating me!
Clean and Bright Stay 2BRM close NU campus
Tracy's home is clean, comfortable, and feels like a great home to return to when you are visiting Evanston. we didn't get a chance to cook in their fabulous kitchen, but I plan to next time!!

Spacious Luxury Townhouse - Old Town
This place is a jem in the heart of an old town. Walkable distance to great restaurants and train station. The neighborhood is quiet and peaceful. For us it was a perfect place to come back to after a day of exploring Chicago. Robert, the host, is super responsive and is very pleasant. Highly recommended!
Family-friendly home rentals with a pool

2 BD 2 BA Abbey Villa with Pool
Great spot! The condo was clean, comfortable, and quiet. It was a short walk to the beach and restaurants. Mandy’s detailed directions and instructions made checking in a breeze. Our group of four had a fantastic time.

2 Bedroom villa at Lake Geneva's GRAND Resort
Clean, roomy place. Short drive to stores or walk/shuttle to resort pool/restaurants. We enjoyed our stay and would definitely stay again. The only disappointment was the golf course was closed.

Abbey Spring Resort Home |North Shore Hideaway
We had a fantastic time here! The property has an incredible deck that extends into the surrounding forest. We had breakfast outside every morning! If you love wildlife, you'll love this place.

Luxury Log Cabin retreat home
Debbie was very communicative before and during our stay. The property has plenty of yard room for outdoor activities and we loved that we didn’t feel stacked up against a bunch of other houses. The driveway can accommodate a group of cars and we loved the reclining couch in the basement. I’d highly recommend this property.

Beautiful 137 Year Old Farm Home (3night min)
Beautiful and eclectic home. It was perfect for our group of girls visiting from all over the U.S to attend our HS Reunion. Plenty of lovely spaces to gather or a private, quiet nook to read or rest. The pool was wonderful. Beds were super comfortable. Kitchen was large enough and well stocked to prepare meals. Andy was very responsive with any issues or questions. Highly recommend!

Lakeview at CasaComo
We absolutely loved this location. We ended up not even going into Lake Geneva until we were driving out. Close to Williams Bay for the Shoreline Trail. Close to restaurants and walking distance to activities. We fished right from the dock and caught a lot of Blue Bill, Northern Pike and Bass. We encountered a lot of wild life; turtles (we watched her laying eggs, cranes, deer, a snake) Pool was fun, listened to music up at the Lodge by the fire and enjoyed the condo. It was very comfortable and welcoming. We will be back!

NEW! Updated Lake Geneva Resort Luxury Suite
We had a great time! The location is perfect and we loved the pool!

Stunning Panoramic Chicago Views & Free Parking
We knew from the photos on the listing that the view was spectacular and that the apartment was nice. We were not prepared for all of the extra, thoughtful touches that were part of this property. It was like staying in a spa! The lavender oil infused warm washcloths, towel warmer, and bathrobes were unexpected and much appreciated! Thank you, Amanda, for having us at your property. We'll be back.
Quick stats about holiday rentals that are family-friendly in McHenry
Total rentals
20 properties
Nightly prices starting at
₹4,317 before taxes and fees
Total number of reviews
1.1K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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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
- 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