Family-friendly vacation rentals in McHenry

4.96 out of 5 average rating, 210 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, 151 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.

4.9 out of 5 average rating, 229 reviews

Guest suite in Zion

Nonsmoking, no cleaning fees, mother-in-law suite.

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, 431 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, 401 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.

4.8 out of 5 average rating, 133 reviews

A serene garden features a flower-filled barrel planters, a stone birdbath, and lush greenery. A calm river is visible in the background, bordered by a wooden bridge and adjacent seating areas, creating a peaceful outdoor space for relaxation.

Apartment in Algonquin

Waterfront Stay w/ Walk to Downtown Entertainment

Apartment overlooking the Fox River. Walking distance to downtown Algonquin. Free wifi & cable TV. Don't impose on family or friends, or settle for the bland experience of a box hotel. Instead, book a comfortable stay with great amenities and enjoy the river and downtown entertainment. You'll be able to relax, get a restful sleep, and enjoy your visit. You'll also notice the little touches and the extra effort made to assure you have an awesome stay. Private Bathroom and Kitchen.

4.96 out of 5 average rating, 196 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, 169 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.

4.9 out of 5 average rating, 353 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.

4.8 out of 5 average rating, 182 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.

Apartment 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.

4.83 out of 5 average rating, 115 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. 💜

5 out of 5 average rating, 175 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, 429 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.

Guesthouse 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.

4.88 out of 5 average rating, 331 reviews

Private Coach house near Lincoln Square!

4.98 out of 5 average rating, 191 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

4.98 out of 5 average rating, 119 reviews

A dining area is presented with a wooden table set for a meal, complete with plates, glasses, and utensils. Light pours in through large glass doors, framing a view of the surrounding trees and outdoor seating on the deck, while a vibrant stained glass window adds a colorful backdrop.

Cabin in Twin Lakes

Secluded in the Woods, Hot Tub

4.95 out of 5 average rating, 137 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

4.86 out of 5 average rating, 207 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

A cozy living area features a dark sofa set against a textured wall, with a small decorative pillow. An open kitchen bar with four modern black stools invites gatherings, while greenery enhances the room's decor. Natural light is filtered through large windows.

4.97 out of 5 average rating, 212 reviews

Relaxing Villa with Amazing Amenities!

4.93 out of 5 average rating, 832 reviews

A treehouse elevated above ground showcases a wooden exterior with a balcony. An inviting staircase leads to the entrance, surrounded by lush greenery and vibrant leaves creating a natural setting. The sturdy structure is supported by wooden beams, blending harmoniously with the surrounding trees.

Treehouse in Schaumburg

Enchanted Garden Treehouse (Amenity*)

Family- and pet-friendly home rentals

4.84 out of 5 average rating, 134 reviews

The exterior of the ranch home is framed by lush greenery and well-maintained landscaping. A stone pathway leads to the entrance, with blooming flowers and shrubs surrounding the home. Large windows allow natural light to brighten the facade, creating an inviting appearance.

Home in Round Lake Beach

Modern 3 bedroom house, quiet residential street.

Guest suite in Portage Park

The living area features a comfortable sofa adorned with colorful cushions, positioned beside a unique wooden coffee table. A striking piece of wall art adds visual interest, while a dining area with modern chairs is visible in the background, complemented by potted plants.

4.94 out of 5 average rating, 444 reviews

Peaceful Portage Park Apartment

4.92 out of 5 average rating, 159 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

4.98 out of 5 average rating, 171 reviews

A fenced backyard features a circular arrangement of wooden lounge chairs centered around a propane fire pit, creating a cozy gathering space. Twinkling string lights hang above, illuminating a bistro table with two blue chairs. Lush green grass surrounds the stone patio area.

Home in Berwyn

Retro Modern Bungalow | fire pit | free parking

4.99 out of 5 average rating, 101 reviews

A stylish living room features two spacious black sofas facing a central coffee table. The room is adorned with a zebra-print rug, and a prominent television is mounted above a textured white fireplace. Natural light filters through large windows, complemented by elegant drapery.

Home in Racine

Stunning Home Across The Street From North Beach

4.9 out of 5 average rating, 243 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, 139 reviews

Eddy Street Upstairs Apartment

Apartment in Jefferson Park

A light-filled dining area features a wooden table surrounded by four chairs. A plush sofa is positioned nearby, offering a cozy option for relaxation. Large windows dressed in navy curtains provide a view of the outside, contributing to an open and inviting feel.

4.95 out of 5 average rating, 240 reviews

Entire 1st Floor Apt near O'Hare/ORD & Blue Line

Family-friendly home rentals with a pool

4.85 out of 5 average rating, 131 reviews

A white motor yacht, named 'Irish Mist,' is docked at Reefpoint Marina. The boat features a spacious top deck with a black canopy and is surrounded by other yachts in the water, with a soft sunset glow illuminating the scene.

Boat in Racine

Vessel: Irish Mist V - 32' @ Reefpoint W1-3

Apartment in Chicago Loop

A bright living area features a comfortable gray sofa and two modern chairs set around a round coffee table. Large windows provide expansive views of the city, while greenery adds a touch of nature to the space. The warm lighting creates a welcoming ambiance.

4.75 out of 5 average rating, 273 reviews

Stunning 3BR Penthouse in the Loop | Roof Deck

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, 161 reviews

LakeView-SummerPool-FamilyFriendly-CloseToTown

4.9 out of 5 average rating, 553 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.

Apartment in Uptown

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

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, 234 reviews

Lake Geneva Cloud 9

4.96 out of 5 average rating, 127 reviews

The living area features a sectional sofa adorned with vibrant cushions beside a coffee table. Natural light filters through large windows dressed with horizontal blinds, illuminating a console with a flat-screen TV and decorative accents.

Condo in Evanston

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

The spacious living room features a large sectional sofa in neutral tones, focused around a gas fireplace. A flat-screen smart TV is mounted above the brick hearth. Sliding glass doors open to the outdoor patio, allowing natural light to fill the space.

4.98 out of 5 average rating, 165 reviews

Quaint Lake Geneva Condo | Fireplace | WiFi

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.