Family-friendly holiday rentals in McHenry

4.96 out of 5 average rating, 213 reviews

Loft in Woodstock

Curated Loft Retreat in The Heart Of Woodstock

Welcome to our spacious upper retreat with modern conveniences. We have great WiFi for you to stay in touch with and are well stocked with books for you to enjoy time unplugged. Close to the Historic Square (you may have seen it in the movie Groundhog Day) you can easily walk to unique shops, cafes, and restaurants. Our curated timeless decor is filled with storied items from our travels, and photos we've snapped locally. Come renew yourself here. We can't wait to share Woodstock IL with you.

5 out of 5 average rating, 161 reviews

Flat in McHenry

Walk to downtown McHenry. Heart of the Fox River

NO PETS Entire 2nd. floor. 1 block away from downtown, Fox River Riverwalk & Pokémon Gym. Full stocked kitchen, books, games, toys & extra amenities to make your stay beyond relaxing. 4:20 allowed in backyard & not in view of under the age of 21. Private smoking area in front too. Minutes away from 2 State Parks, 1 with free boat/kayak launch. Several marinas, boat rental, golf courses & huge variety of entertainment. Look at Bettye's Guidebook for more information & nearby entertainment.

4.93 out of 5 average rating, 126 reviews

A bright living area features a comfortable sofa arranged around a modern coffee table. A work desk is positioned near the window, with natural light spilling in. Artwork adorns the walls, and greenery adds a touch of life to the space, enhancing the welcoming atmosphere.

Flat in West Dundee

Charming Riverfront Stay | Heart of Downtown

Welcome to The Riverfronts! Three boutique hotel rooms perfectly situated along the river in downtown West Dundee, offering scenic views and modern comforts. ✔ Riverfront Location: Enjoy the scenic riverwalk just steps away. ✔ Prime Downtown Spot: In the heart of downtown Dundee, minutes from top attractions and dining. ✔ Exclusive Group Booking: Reserve just one or all three units for your entire party. ✔ Outdoor Firepit: Unwind by the firepit, perfect for evening gatherings. ✔ Sleeps 4: Each

4.91 out of 5 average rating, 239 reviews

Guest suite in Zion

Nonsmoke, No Cleaning Fees, No Long Chore Lists.

25 minutes away from the Naval Station 5 minutes away from the beach. 10 minutes to Wisconsin. 1 hour 40 minutes to O’Hare Airport and downtown Chicago. 40 minutes to Milwaukee Airport 25 minutes to Six Flags and Great Wolf Lodge. Safe and quiet neighborhood with plenty of wildlife right in the back yard. This Mother in Law suite has tons of natural light. For nature lover’s this unit is close to the beach and there are walking trails nearby. Small children maybe heard from 7AM to 8PM.

Guest suite in Riverwoods

A well-defined stone pathway leads to the entrance of the prairie-style home, bordered by lush green grass and neatly trimmed hedges. Hanging flower baskets add vibrant touches above the cozy seating area, surrounded by the serene backdrop of towering oak trees.

4.95 out of 5 average rating, 445 reviews

Master qtr close to nature & easy urban facilities

This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

4.96 out of 5 average rating, 199 reviews

A historic stone home built in 1911 is prominently featured, showcasing its grand architectural details. The façade includes a porch supported by strong columns. A group of individuals stands in front, illustrating the home's welcoming presence in its early days amidst a natural landscape.

Guest house in McHenry

"The Apartment" in the heart of downtown McHenry

We welcome you to be our guest in this charming, historic home built in 1911 by a German mason. This upper unit Apartment is a spacious 1,100 square feet, lovingly restored with a vintage aesthetic in 2018. The private entrance to "The Apartment" will lead you to; 2 cozy bedrooms & 1 vintage inspired yet modern bath with walk in shower. A large living room, dining area and bright clean kitchen will make you feel right at home. 9 foot ceilings and tons of natural light through out.

4.99 out of 5 average rating, 178 reviews

A serene living area features a large sliding glass door leading to a deck with unobstructed views of Round Lake. Natural wood accents adorn the wall, while a plush sofa and a small coffee table create a relaxing seating space.

Home in Round Lake Beach

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Townhouse in Hoffman Estates

A cozy living area features a black leather sofa paired with decorative pillows. A glass coffee table sits atop a patterned rug, complemented by a lamp and a small plant. The staircase leads to an upper level, with a wall map artwork enhancing the space.

4.89 out of 5 average rating, 361 reviews

a SIMPLE place

Booking the entire house with 100% privacy. It has 2 driveway parking spaces and street parking. Garage may be available. CHECK-IN and OUT are flexible. I set checkout at 11am (text me if you need late checkout). The space is perfect for a family of 4. It is located about 20 minutes from O'Hare airport and 40 minutes from Chicago downtown. Infants and pets are welcome (please text me for over size pets or more than 2 pets) Play pan is available upon request.

4.81 out of 5 average rating, 186 reviews

The exterior of the Victorian Sherwood House showcases its distinct pink siding accented with green trim. Stained glass windows add character, and multiple gabled roofs enhance its architectural design. A canopy of trees provides a natural backdrop to this charming residence.

Flat in Elgin

Sherwood House

Enjoy the ambience of the Sherwood House, an 1884 Victorian built for Judge David Sherwood. Use of entire first floor apartment including a full kitchen is perfect for longer term stays. Original features include multiple stained glass windows, beautiful wood work, multiple decorative fireplaces and hardwood floors. Located just blocks from downtown Elgin, walk to shops, restaurants, the casino, bike trail or Metra. WiFi and off street parking.

Superhost

A cottage exterior is showcased with a well-maintained wooden deck and black railings. A welcoming front door is featured, which is flanked by two windows. The surroundings include a manicured lawn with small flower beds, enhancing the cottage's inviting appearance.

Cottage in Antioch

4.83 out of 5 average rating, 118 reviews

#4: Cute 2 bedroom cottage on the beach!

Come relax at Turtle Beach Marina! Rent a Pontoon or a Kayak. Spend the day at the beach and at the beach bar (Beach bar is open mid May until the last weekend in October). There is a restaurant and gaming room (slots) on the property. Quaint cottage has 2 bedrooms with a full bed in each. Up to 4 people allowed. There is no oven but has a 2 burner electric cook top. A grill is also available. Beach themed cottage is completely remodeled. 💜

5 out of 5 average rating, 179 reviews

The exterior of the apartment is shown, featuring a light gray siding and a covered porch. Lush green grass surrounds the building, highlighted by well-maintained flower beds with blooming plants. Large windows allow natural light to flow into the living space.

Flat in Cary

A Peaceful Get-Away

Come and enjoy the quiet of nature. We are located off the beaten path, near the Fox River, but less than three miles from the Metra station (into Chicago); and less than five miles from the Norge Ski Club. Within driving distance, there are golf courses, hiking paths, and shopping. Our fully furnished apartment is attached to our main house and offers you a private entrance and driveway parking for one vehicle.

Home in Fontana-on-Geneva Lake

A small potted plant sits atop a wooden shelf, accompanied by blocks that spell out 'WELCOME.' The blocks are arranged in a neat line, showcasing a modern and friendly presentation.

4.94 out of 5 average rating, 219 reviews

The Little Farm Fontana 5 min from Geneva Lake!

Cozy cottage less than 2 miles from Fontana Beach and the sought after Geneva Lake! Minutes away from The Abbey Resort and just across the street from Abbey Springs Golf course, relax in this beautifully located home away from home out in the country with the luxury of quick and easy access to shopping and dining. We are within 15 minutes of downtown Lake Geneva if you are planning a day trip or a night on the town.

Popular amenities for McHenry family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.88 out of 5 average rating, 104 reviews

A spacious outdoor deck is covered with a bright shade sail, providing relief from the sun. Comfortable wicker chairs with soft cushions create a cozy seating area, overlooking the peaceful river and surrounding greenery.

Home in Algonquin

The River House Sauna/Kayaks/Hot Tub/Fire Pit

4.97 out of 5 average rating, 437 reviews

A welcoming living area is showcased, featuring a comfortable seating setup with a gray armchair and a round coffee table. Soft light filters through sheer curtains, illuminating the space. An intricately designed wall decoration adds an aesthetic touch beside a black bench with decorative elements.

Flat in Beach Park

J’s Farmhouse Cottage. 2 bedroom duplex.

Guest house in Lincoln Square

The exterior of a charming coach house is presented, featuring wooden shingles and a well-maintained yard. A circular table with chairs is set on the lawn, accompanied by a green umbrella for shade. Lush bushes border the property, and a wooden fence encloses the yard.

4.89 out of 5 average rating, 343 reviews

Private Coach house near Lincoln Square!

A spacious living room features comfortable seating arrangements, including a sleeper sofa and armchair. Natural light filters through large sliding doors, leading to a balcony. A cozy gas fireplace adds warmth to the space, complemented by a round coffee table and a flat-screen TV mounted on the wall.

4.94 out of 5 average rating, 203 reviews

Beautiful Villa with Amenities Galore

4.99 out of 5 average rating, 205 reviews

A private hot tub is set in a shaded outdoor area, surrounded by wooden fencing. The tub features jets and is filled with bubbling water. Steps lead up to the hot tub, and a patterned area rug lies nearby, enhancing the relaxing space.

Cottage in Racine

Clementine Cottage

Cabin in Fontana-on-Geneva Lake

An A-frame structure is nestled among lush green trees, showcasing large glass windows that allow for ample natural light. The contrasting wood siding complements the surrounding foliage, creating a harmonious blend with nature. A raised deck leads to the entrance, enhancing accessibility to the home.

4.93 out of 5 average rating, 166 reviews

Exquisite Modern A-frame all WithInnReach

4.95 out of 5 average rating, 145 reviews

A spacious bathroom features large skylights that illuminate a freestanding tub, set beneath an arched window overlooking greenery. Two modern lounge chairs are situated nearby, enhancing the tranquil ambiance. The glass-enclosed shower and soft neutral tones create a serene and relaxing environment.

Farm stay in Harvard

Eden Farm: Family Stays & Intimate Moments

4.97 out of 5 average rating, 149 reviews

The game room features a red-themed layout filled with arcade machines, a pool table, and foosball. A variety of classic games are showcased, providing a fun atmosphere for guests. Bright lighting illuminates the room, inviting enjoyable gaming experiences.

Flat in Dunning

Belmont Pleasures - hot tub / arcade gaming room

Family- and pet-friendly home rentals

4.93 out of 5 average rating, 176 reviews

A welcoming living area is presented, featuring a spacious black sectional sofa and a cozy round chair. Natural light floods in through sliding glass doors, leading to an outside view. A subtle decor with plants and a table lamp adds to the inviting ambiance.

Home in Lake Geneva

Lake Geneva cottage with private beach access

4.87 out of 5 average rating, 399 reviews

A cozy living area is highlighted by a colorfully decorated Christmas tree with red ornaments and lights. A festive banner reading "Merry Christmas" hangs above. A plaid sofa is positioned beside the tree, adorned with pillows featuring a reindeer motif.

Guest house in East Troy

Deligo Valley Cottage

4.98 out of 5 average rating, 127 reviews

A living area features a stone fireplace and large windows providing views of Lake Beulah. Comfortable seating surrounds a wooden coffee table. A dining table is visible, alongside decor elements that create a cozy ambiance. Natural light floods the space, enhancing the connection to the outdoors.

Home in East Troy

Lakeside Getaway

4.88 out of 5 average rating, 155 reviews

The sunroom features large windows providing views of the serene pond and natural surroundings. Cozy seating areas with blue cushions are present, along with a coffee table at the center. A ceiling fan offers airflow, contributing to a tranquil atmosphere.

Home in Lake Geneva

Charming Lake Geneva, Wisconsin 3BR/2Bath Home

4.98 out of 5 average rating, 183 reviews

A living room features a mid-century velvet sofa in a rich green hue, paired with a tan leather chair. Natural light streams through large windows, illuminating a glass coffee table and a decorative wall with layered wooden frames. The original brick fireplace adds character to the space.

Home in Berwyn

Retro Modern Bungalow | free parking | fire pit

4.97 out of 5 average rating, 238 reviews

The entrance of the A-Frame cabin features a wooden door framed by large windows. Two black wire chairs sit on a wooden deck, complemented by potted plants. Natural surroundings enhance the welcoming feel of the entrance.

Cabin in Lake Geneva

Winter Wonderland A-Frame - Dog Friendly!

Guest suite in Portage Park

A spacious living area features a large television mounted above a low bookshelf filled with books and movies. A wooden coffee table sits at the center, complemented by a light-colored couch. Doorways lead to other areas, with a hint of the kitchen visible in the background.

4.96 out of 5 average rating, 144 reviews

Eddy Street Upstairs Apartment

4.89 out of 5 average rating, 135 reviews

The exterior of a charming historic home features dark blue siding and a welcoming front porch with three steps leading up to the entrance. Large windows on either side of the door allow for natural light, while lush greenery surrounds the property, enhancing its curb appeal.

Home in Elgin

Charming Elgin Home with a Great Location

Family-friendly home rentals with a pool

4.84 out of 5 average rating, 108 reviews

A modern living area features a light-colored sofa adorned with decorative pillows, set against large floor-to-ceiling windows that offer views of the city skyline. A textured area rug defines the space, while a coffee table displays artfully arranged decorative items. A dining table with black chairs completes the setting.

Flat in West Loop

Top Floor Views + Central Comfort

Superhost

A cozy corner of the living room features a brick fireplace with a warm fire. A decorative candle holder stands beside a beautifully lit Christmas tree. A plush sofa, adorned with a patterned pillow, invites relaxation, while a simple table holds a remote and holiday decor.

Apartment in Fontana-on-Geneva Lake

4.78 out of 5 average rating, 195 reviews

FUN-tana All Year Round Abbey Springs Fontana WI

The living area features a dark leather sofa adorned with blue throw pillows, accompanied by a light gray couch. A round woven pouf and an antique-style trunk serve as accent furniture. Large glass doors provide access to a balcony, with lake-themed decor on the wall.

4.96 out of 5 average rating, 165 reviews

LakeView-SummerPool-FamilyFriendly-CloseToTown

An open kitchen area is showcased with a wooden dining table and two white chairs. Modern appliances, including a microwave and a decorative wall with floral wallpaper, add a touch of charm. An oversized clock hangs above, contributing to the inviting ambiance.

4.91 out of 5 average rating, 106 reviews

LG Quaint Condo on Lakeshore Dr.

4.9 out of 5 average rating, 563 reviews

A cozy bedroom features a spacious bed dressed in bold black and white striped bedding. A decorative red pillow adds a pop of color. A framed artwork of a rabbit is displayed above the bed, complemented by bedside tables with a lamp and a small potted plant.

Flat in Uptown

Whole Flat in Private Club. Walk to L, Dining & Shows

4.86 out of 5 average rating, 119 reviews

A spacious driveway leads to a modern log cabin home surrounded by greenery. Flanking the driveway are several well-maintained evergreen trees. The cabin features a warm orange exterior, complementing the natural setting, with a stone accent wall visible on one side.

Cabin in Lake Geneva

Luxury Log Cabin retreat home

A spacious living area features a large sectional couch and a soft ottoman. A wooden table stands nearby, with a laptop resting on it. The kitchen area is visible, showcasing a bar with seating for four. Soft lighting enhances the neutral color palette.

4.87 out of 5 average rating, 119 reviews

Lake Geneva relaxation!

A manicured lawn gently slopes towards a serene body of water in the distance, framed by tall trees on either side. The landscape features lush greenery under a partly cloudy sky, creating an open and inviting outdoor space.