Family-friendly vacation rentals in McHenry

4.96 out of 5 average rating, 211 reviews

An open living area features a cozy workspace with a desk and chair beside a vibrant area rug. Natural light filters through large windows, illuminating a relaxed seating space with a lamp and plants. The adjoining kitchen with blue cabinets and a cart is visible in the background.

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, 156 reviews

Apartment 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, 116 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.

Apartment 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

4.89 out of 5 average rating, 132 reviews

An expansive indoor pool area is showcased, featuring a spacious heated sport pool and a circular hot tub. Large windows provide natural light and views of the outdoors, while decorative plants add a touch of greenery. A large TV is mounted nearby, enhancing the area’s entertainment options.

Home in McHenry

Highwood Haven/Indoor Pool/Hot Tub/Arcade

Unwind at Highwood Haven, an opulent McHenry getaway with a heated indoor pool and arcade. Savor culinary delights in our chef's kitchen, enjoy al fresco entertainment, and relax in sumptuous bedrooms. An hour from Chicago, it's ideal for luxury retreats and family fun. Revel in our nine-person hot tub, outdoor lounge with TV, and serene bedrooms. Make memories with both lively entertainment and tranquil moments, all within a luxurious setting. Your perfect destination for an upscale vacation.

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, 435 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.

Farm stay in Cherry Valley

A spacious outdoor area features a fire pit surrounded by seating. In the background, a large barn with a green and white exterior is visible, set against a serene landscape of lush grass and trees.

4.98 out of 5 average rating, 408 reviews

Bed and Breakfast with Horse Hotel at VRR

Victory Reigns Ranch Horse Hotel and Bed and Breakfast boasts a beautiful ranch setting close to Deer Run Forest Preserve, Oak Ridge Forest Preserve and other equestrian trails. *Come with or without your horse. We also have an RV hookup if needed along with spacious trailer and RV parking. *If interested in horse boarding during your stay a 12 x 12 barn stall is $35 per night. Private pasture turn out available for $25 per horse per night. Trailer hook up is $35 per night per trailer.

4.95 out of 5 average rating, 209 reviews

A spacious living area is highlighted by large windows offering views of the water. Colorful seating options, including bean bags and patterned chairs, complement a wooden coffee table. Sleek ceiling fixtures and a soft rug define the gathering space, enhancing the open layout.

Home in Richmond

TheGlassCabin @ HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

4.96 out of 5 average rating, 198 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.

Guesthouse 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, 172 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!

4.83 out of 5 average rating, 118 reviews

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: 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. 💜

A cozy bedroom features a plush king-sized bed with a light-colored duvet and decorative cushions. Natural light enters through large windows adorned with soft curtains. A comfortable bench sits at the foot of the bed, alongside a dark wood dresser and a small television.

4.97 out of 5 average rating, 115 reviews

The Landis, elegant with fireplace!

Kick back and relax in this calm, elegant One bedroom Villa with a KING size bed. This vacation rental is in a quiet area of Lake Geneva, but just minutes from all the vibrancy of downtown Lake Geneva or Williams Bay. It is within walking distance to Mars Resort, The Getaway or The Ridge. This is a perfect spot for couples looking for a relaxing getaway. Local laws require all guests names and address be provided prior to check in.

5 out of 5 average rating, 178 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.

Apartment 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.

Popular amenities for McHenry family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 432 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.

Apartment in Beach Park

J’s Farmhouse Cottage. 2 bedroom duplex.

4.94 out of 5 average rating, 103 reviews

The spacious lakehouse exterior features a blue façade with white trim, accentuated by a welcoming front porch. Vibrant flower beds and lush landscaping surround the property, while large windows offer glimpses of the lake. An American flag adds a touch of charm to the inviting entrance.

Home in Lake Geneva

The Ultimate Lakehouse with Hot Tub & Pier

4.98 out of 5 average rating, 197 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

4.86 out of 5 average rating, 233 reviews

The interior of the cottage features a cozy seating area with a blue couch adorned with yellow cushions. A coffee table made of wicker sits atop a soft yellow rug. A kitchenette is visible, along with a dining area illuminated by natural light from large windows.

Cottage in Antioch

#5 Tiny Lake Cottage at Cypress Resort & Marine

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.

4.92 out of 5 average rating, 159 reviews

Exquisite Modern A-frame all WithInnReach

4.95 out of 5 average rating, 140 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

4.87 out of 5 average rating, 210 reviews

A spacious living area features high, wooden beams and large windows allowing natural light. A stone fireplace is positioned centrally, accompanied by a cozy seating arrangement. A dining table sits adjacent, surrounded by earthy decor, enhancing the rustic ambiance.

Cabin in Delavan

Cabin Outdoor HotTub Sleeps 7 Pet Friendly

4.89 out of 5 average rating, 123 reviews

A warm living space features a stone fireplace with a lit fire, complemented by a wall-mounted television above. A small game area with checkers is set on the floor. A wooden cabinet displays decorative items, while cozy blankets are neatly arranged nearby.

Home in Fox Lake

Lakefront Winter Getaway with Hot Tub!

Family- and pet-friendly home rentals

Guest suite in Naperville

A tranquil lake scene is depicted, featuring autumnal trees reflecting vibrant hues of yellow, orange, and red in still water. The grassy shoreline enhances the serene environment, while neighboring greenery contributes to the picturesque landscape.

4.96 out of 5 average rating, 476 reviews

Cozy Lakeview Studio with Private Access

4.93 out of 5 average rating, 170 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

4.93 out of 5 average rating, 161 reviews

Cottage in Wonder Lake

The Christmas Cottage/ Lake Front Property

4.97 out of 5 average rating, 236 reviews

The A-frame cabin is framed by lush greenery, showcasing a welcoming front entry with large windows. The pathway is lined with manicured hedges, leading to a solid wooden door. The natural surroundings enhance the feel of a secluded retreat.

Cabin in Lake Geneva

Charming A-Frame - Dog Friendly!

4.9 out of 5 average rating, 245 reviews

A rustic cabin with dark wooden logs is situated among tall green trees. The spacious porch features a railing and several chairs, inviting relaxation. Sunlight casts warm tones across the facade, while the surrounding grass and woods enhance the cabin's natural setting.

Guesthouse in Racine

Charming log cabin in the woods

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, 141 reviews

Eddy Street Upstairs Apartment

4.89 out of 5 average rating, 131 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

4.97 out of 5 average rating, 847 reviews

A spacious living room features three large windows allowing natural light to fill the space. Comfortable seating includes a leather couch and an armchair. A television is mounted on the wall, and a decorative area rug lies beneath a wooden table set for dining.

Condo in Noble Square

Great location. Free parking.

Family-friendly home rentals with a pool

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

4.91 out of 5 average rating, 104 reviews

A rooftop pool area is shown, featuring a clear blue pool surrounded by lounge chairs in red and neutral tones. Sunlight reflects off the water, and tall buildings are visible in the background, contributing to a lively urban atmosphere.

Apartment in South Loop

The Professional's Playground (2BD / 2BA)

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.

4.9 out of 5 average rating, 102 reviews

LG Quaint Condo on Lakeshore Dr.

4.86 out of 5 average rating, 118 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.

4.98 out of 5 average rating, 237 reviews

Lake Geneva Cloud 9

An open living and dining area features a dark wooden dining table surrounded by black chairs. A light blue wall complements a cozy seating arrangement with armchairs and a sofa. Natural light enters through a large sliding door, with decorative elements and a chandelier enhancing the space.

4.9 out of 5 average rating, 207 reviews

Lakeview at CasaComo