Family-friendly holiday 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, 155 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

A cozy living area is highlighted by a gas fireplace and a large Smart TV mounted on the wall. A sliding glass door leads to a balcony with views of the green courtyard. Comfortable seating is arranged around a rustic coffee table that complements the relaxed atmosphere.

4.98 out of 5 average rating, 162 reviews

Lake Geneva Getaway! King Bed! Fireplace!

Your cozy & relaxing getaway begins in a newly redesigned condo with balcony (courtyard view), and is conveniently located between Lake Como and Lake Geneva in peaceful Interlaken Resort community! Just a short peaceful walk to lake, restaurants, pool, tennis, volleyball, boat launch, small craft rentals, and more! The resort community is located by Lodge Geneva National (formerly The Ridge Hotel), which adds additional restaurants and available amenities at an additional charge. Walk to the

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.

4.91 out of 5 average rating, 235 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.

Place to stay in Crystal Lake

5 out of 5 average rating, 124 reviews

Couples Getaway! Hot Tub, Lake, Fire Pit, Trails

Private entrance to a stunning master suite.A VERY unique property.Sliding suite door opens to screened in pool room. Hot tub all year overlooking my private lake. Pool closed Oct. 1st. Seating area & TV to watch while lounging & swimming. (2) Kayaks 4 you. Walking & bike trails. I am minutes from everything U want. Grill, have a fire in the fireplace&fire pit.Bring your fishing poles! Time 2 RELAX in privacy. When not traveling, I live in main part of home. You won’t see me. No extra guests.

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.

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, 170 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. 💜

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

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.97 out of 5 average rating, 431 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.

4.98 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

4.98 out of 5 average rating, 125 reviews

The great room features vaulted wood trusses and large windows that allow natural light to fill the space. A dining table is positioned centrally, surrounded by four chairs. Two rocking chairs are placed at opposite ends, with a decorative rug on the wooden floor.

Cabin in Twin Lakes

Secluded in the Woods, Hot Tub

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

4.89 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!

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, 214 reviews

Relaxing Villa with Amazing Amenities!

4.97 out of 5 average rating, 144 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.

Apartment in Dunning

Belmont Pleasures - hot tub / arcade gaming room

Family- and pet-friendly home rentals

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, 452 reviews

Peaceful Portage Park Apartment

4.93 out of 5 average rating, 161 reviews

Cottage in Wonder Lake

The Cozy Lake House/Perfect Lake Front Getaway!

4.98 out of 5 average rating, 176 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, 104 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

4.97 out of 5 average rating, 235 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

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, 356 reviews

a SIMPLE place

Family-friendly home rentals with a pool

Condo in Fontana-on-Geneva Lake

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.

4.78 out of 5 average rating, 195 reviews

FUN-tana All Year Round Abbey Springs Fontana WI

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

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.

4.9 out of 5 average rating, 102 reviews

LG Quaint Condo on Lakeshore Dr.

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 CasaCome