Family-friendly holiday rentals in Willoughby

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Top-rated family-friendly rentals in Willoughby

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
A cozy indoor space features a spacious bed with rustic wooden accents and layered textures. A comfortable sectional sofa is adorned with soft throws and cushions. Natural light filters through large windows, illuminating a decorative console table with sunflowers and various books.
Barn in Mantua
4.95 out of 5 average rating, 104 reviews

Farm Stay in Luxury Barndominium Mantua Ohio

Welcome! Experience our rural farm’s abundance! Take a magical walk through the charming vegetable and flower gardens. Enjoy a beautiful, tranquil stocked fishing pond & Scottish Highlander cattle. If your spirit calls you further take your adventures to the Cuyahoga River, just a stones throw away for kayaking, canoeing, & tubing. After experiencing nature’s gifts outdoors, rest and recharge indoors while connecting to your creative side enjoying the Artist’s inspiration within the loft space.

Top guest favourite
The family room features a cozy electric fireplace surrounded by built-in shelves filled with books and decorative items. A large mirror above the fireplace reflects natural light. Light-colored seating is arranged on a blue area rug, enhancing a relaxing atmosphere.
Home in Willowick
4.96 out of 5 average rating, 271 reviews

Lake Erie Getaway

Enjoy the wondrous beauty and sunsets of Lake Erie, the 11th largest freshwater lake in the world. From the back yard you can swim or fish. 2 bedroom/2 bathroom house with cozy electric fireplace in family room . 1300 square feet of first floor living on Lake Erie.Lake views from nearly every room. Private fenced backyard with over 400 plants. Twenty minutes from downtown Cleveland and University Circle area, 10 minutes to downtown Willoughby and a 5 minute walk to the grocery stores and deli

Top guest favourite
An inviting kitchen area features modern cabinetry and a round dining table, complemented by plush seating. A well-decorated bedroom showcases a spacious bed, with natural light flowing through the window. The backyard offers a serene green space, perfect for relaxation. Living spaces are comfortably furnished.
Home in Willoughby
4.98 out of 5 average rating, 166 reviews

Retreat at DTW

Come relax & enjoy The Retreat at DTW! Just minutes away from Historic Downtown Willoughby where you can shop, dine & stroll the streets at your leisure. This completely renovated single family ranch home has so much to offer. Including all kitchen appliances, washer & dryer, all necessities (kitchenware, towels, sheets, etc.) & playing cards plus board games for your pleasure. The bedroom has a king bed & living room has a sofa bed. Enjoy the reading nook on the 2nd level loft area & backyard.

Top guest favourite
A spacious deck offers a panoramic view of Lake Erie, with sunlight reflecting on the water. Two chairs surround a simple table, inviting relaxation. The deck is bordered by vibrant greenery, and a warm glow is cast over the scene by the setting sun.
Cottage in Willowick
4.97 out of 5 average rating, 326 reviews

Lake House with Amazing Views

Amazing location right on Lake Erie. This cozy lake house has a large kitchen, full bathroom and a living room/bedroom with king-size bed. The cottage is off by itself so you can enjoy your seclusion, but we live about 200 feet away so we can assist you if you need us. Enjoy a morning coffee on the deck while watching nature, spectacular sunsets on the private patio, and falling asleep to the sounds of the lake. You will be blown away by the beauty and peacefulness of this amazing cottage.

Top guest favourite
Cabin in Middlefield
4.96 out of 5 average rating, 105 reviews

The Wildflower

Come enjoy this brand new cabin in a private wooded setting. Sit on the front porch swing or relax by the fireplace. Enjoy the whirlpool for two and new stylish decor with black metal railing against a backdrop of the finest craftsmenship of woodworking. This cabin was built by local Amish and Mennonite builders. There is a double reclining loveseat and a queen size pull out sofa with a memory foam mattress. We provide snacks, sodas, coffee, tea, cereal, juice, pancaKe mix & maple syrup!

Top guest favourite
A welcoming living area features two upholstered armchairs flanking a glass-top coffee table, which rests on a soft area rug. Wall art with floral designs adds a touch of character, while lamps provide soft illumination, creating a cozy ambiance. The space opens to a dining area in the background.
Home in Mentor
4.96 out of 5 average rating, 174 reviews

COZY Centrally Located Gem-King*Hot Tub*Lake Erie

Welcome to Our Mentor Bed & Breakfast! Experience comfort, convenience, and charm at our cozy pet-friendly bed & breakfast located in one of Mentor’s most walkable neighborhoods. Step outside and enjoy nearby restaurants, cafés, bars, and everyday essentials just steps away. Relax in the hot tub, explore Ohio’s largest beach-6 miles away, visit local wineries, or take a short 30-minute trip to Cleveland for city adventures. Need more space? We offer an optional in-law suite for larger groups.

Top guest favourite
Home in Wickliffe
4.98 out of 5 average rating, 126 reviews

Mid-Century Modern Ranch in quiet neighborhood

Stay in our newly remodeled Mid-Century classic! It's updated to incorporate today's conveniences with focus on the original vision of the 1965 builder who constructed it for its long time owners. Located just off Interstate 90 in a quiet neighborhood, the home offers an open living space, a lower level recreation room for playing pool or ping pong, a large fenced in yard, and a covered back porch to enjoy morning coffee or an evening glass of wine as you watch the many neighborhood deer.

Top guest favourite
Guest house in Chardon
4.96 out of 5 average rating, 304 reviews

Chardon Loft

Large private 2nd floor studio style living area with queen size bed, couch, table/chairs, TV, refrigerator, microwave, hot plate, NO OVEN OR STOVE TOP, sink, large shower, A/C, heat, washer and dryer, and deck. Wifi internet is provided. The television has Netflix. No cable channels. The furnace is nontraditional. It is not located in a closet. The noise when running and starting will be louder than normal during winter months. Ear plugs are available for those that are noise sensitive.

Top guest favourite
A spacious backyard is highlighted by a large, weeping willow tree providing shade over a grass area. Outdoor seating with lounge chairs is positioned facing Lake Erie, offering a view of the water. A peaceful atmosphere is accentuated by a small decorative planter in the foreground.
Cottage in Willoughby
4.99 out of 5 average rating, 206 reviews

Lydia's Lake Erie Cottage

In the heart of Willoughby, a cozy cottage awaits you as the perfect getaway spot. Situated on the shores of Lake Erie, you'll be able to enjoy stunning lake views on the water's edge. Inside, you'll find a cozy and well-appointed space, complete with a fully stocked kitchen and outdoor grill, Unwind by the fireplace in the living room or catch up on your favorite shows on the smart TV. Stay connected with the free WiFi, and take advantage of the laundry with a washing machine and dryer.

Top guest favourite
A spacious studio layout is visible, featuring a plush couch facing a round dining table with four wooden chairs. A comfortable bed with a checkered duvet is positioned nearby, while a well-equipped kitchenette and natural light streaming through the window enhance the welcoming atmosphere.
Flat in Willowick
4.95 out of 5 average rating, 127 reviews

Residential Apartment w/Drumkit

Quiet apartment in residential neighborhood attached to owner occupied home. Beautiful scenic large backyard with dining area & fire pit. Electronic Roland, TD-8 drum kit to be enjoyed by everyone: If you’ve ever wanted to play the drums and haven’t had a chance, or if you are a current player looking to keep your chops in shape!! Located 25 min. from Cleveland with a beautiful Great Lake (Erie) at the end of the st.&Lakefront Lodge Park 1/2 mi. Many food/grocery establishments nearby.

Guest favourite
A bright living area features a combination of leather and upholstered seating arranged around a coffee table. Large glass sliding doors provide sweeping views of the lake, allowing natural light to fill the space. A decorative rug adds warmth to the hardwood floor.
Home in Willoughby
4.95 out of 5 average rating, 105 reviews

Contemporary Lake Home | Sunrise & Sunset Views

This beautifully updated lakefront home is perfect for family gatherings, friend reunions, bachelor/bachelorette parties, or a relaxing retreat. Enjoy breathtaking sunrise-to-sunset views over the lake. Located near Downtown Willoughby, restaurants, and just 20 minutes from Cleveland. The spacious kitchen is perfect for creating meals and memories, and outside you'll find a BBQ and firepit. Pets are welcome for a small fee, so bring your furry friends along for the getaway!

Top guest favourite
A welcoming entrance features a vibrant yellow door surrounded by decorative garlands and twinkling lights. A white wreath adorns the door, while a festive snowman stands on the stone steps, complemented by a red scarf. A snowflake decorates the adjacent wall.
Guest house in Chardon
5 out of 5 average rating, 157 reviews

Private, Quiet 1 BR 1 Bath Chardon Guesthouse

Enjoy a respite at this peaceful and centrally-located, newly renovated guesthouse. Large 1BR w full bath. Sleep with the windows open - it's that quiet. Living room and full, eat-in kitchen. Private patio for outdoor dining. Walk to historic Chardon Square and enjoy its many festivals & activities. Easy drive to Amish country, wineries, Lake Erie and its coastal towns and beaches, The Great Geauga County Fair, 40 minutes to downtown Cleveland.

Popular amenities for Willoughby family-friendly rentals

When is the best time to visit Willoughby?

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Avg. price$171 SGD$172 SGD$175 SGD$170 SGD$175 SGD$185 SGD$205 SGD$209 SGD$196 SGD$191 SGD$200 SGD$217 SGD
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Quick stats about holiday rentals that are family-friendly in Willoughby

  • Total holiday rentals

    Explore 40 holiday rentals in Willoughby

  • Nightly prices starting at

    Willoughby holiday rentals start at $102 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,960 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    40 of Willoughby holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Willoughby rentals

  • 4.8 Average rating

    Willoughby stays are highly rated by guests – averaging 4.8 out of 5!

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