Holiday rentals in Willoughby

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Top-rated holiday rentals in Willoughby

Guests agree: these stays are highly rated for location, cleanliness and more.

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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, 172 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
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, 274 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
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, 329 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.

Guest favourite
Cabin in Middlefield
4.96 out of 5 average rating, 112 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
The exterior of a modern ranch house is showcased, featuring a vibrant red façade and a metal roof. A spacious deck is visible, complete with outdoor seating and a view of the nearby creek and surrounding trees. A gravel driveway leads to the entrance.
Home in Garrettsville
4.99 out of 5 average rating, 532 reviews

“Willow Ledge at Silver Creek”with Private Hot Tub

New Construction Modern Ranch House features rustic upscale design with beautiful cozy interiors and comfort at every turn. Stunning views await with floor to ceiling windows overlooking beautiful Silver Creek and surrounding nature. Private deck is spacious and inviting with oversize hot tub, concrete fire pit, gas grill, and outdoor dining furniture. A few minutes from great restaurants, the Brewery at Garrett’s Mill, and the coolest Coffee Shop. Perfect weekend getaway or business stay.

Top guest favourite
Home in Wickliffe
4.98 out of 5 average rating, 129 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
A welcoming living and dining area features comfortable, woven dining chairs surrounding a glass table. Natural light floods the space through sliding glass doors, offering views of the expansive deck and lake beyond. Potted plants add greenery to the bright and airy atmosphere.
Home in Willoughby
5 out of 5 average rating, 111 reviews

Upscale-Lakefront-Private Beach-Hot Tub-King-Pets

Lakeside living at its finest. This amazing oasis is comfy and inviting with stunning views, expansive deck, and your own private beach. Fully renovated, carefully curated and meticulously cleaned-this indulgent gem is perfect for a serene dip in the hot tub at sunset or easy fishing from the shore. Relax and watch the boats, eagles and waves-everything has been thought of here. Your spacious master suite looks out over a second-floor balcony. A perfect place to enjoy the in-room coffee bar.

Top guest favourite
Guest house in Chardon
4.96 out of 5 average rating, 327 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, 207 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.

Guest favourite
A spacious living area is presented, featuring a comfortable sofa and a soft area rug. A modern coffee table sits in the center, while a large TV is positioned against the wall. Natural light filters in through sloped ceilings and a nearby window.
Flat in East Cleveland
4.99 out of 5 average rating, 136 reviews

New! “Modernistic Retreat”

Elevate your stay in this bright, elegant and spacious 3rd floor apartment that offers the perfect blend of tranquility and urban convenience. Less than 10 minutes from Cleveland Clinic, 8 min from Case Western University, 17 min from Rock and Roll Hall of Fame, 18 min from Cleveland Browns Stadium, 20 min from Downtown, 28 min from Cleveland Airport and 45 min from Blossom Music Venue. Moments from charmed local neighborhoods such as Coventry, Little Italy, Cedar Fairmont and Lee Rd.

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
4.96 out of 5 average rating, 137 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.

Top guest favourite
A cozy outdoor seating area is outlined by decorative flowers and gravel. Two wooden chairs are positioned to overlook Little Punderson Lake, framed by lush trees and a stacked stone feature. Natural light filters through the surrounding greenery.
Home in Burton
4.98 out of 5 average rating, 127 reviews

Rocking H Lakefront Cottage

Come unwind at this lakeside cottage on Little Punderson Lake. Watch eagles and herons from your morning coffee or enjoy sunsets with wine. Guests love this peaceful spot to recharge. Next to Punderson State Park with trails, fishing, kayaking, and golf. Near Amish country with great restaurants. A true rural getaway. Please read full description before booking.

Popular amenities for Willoughby holiday rentals

When is the best time to visit Willoughby?

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Frequently Asked Questions

  • What are the best places to stay in Willoughby?

    Many visitors choose to stay near Willoughby's historic downtown, which has walkable access to local shops, restaurants, and community events. Neighborhoods around parks and quiet residential streets are frequently selected for a more relaxed atmosphere.

  • What are the best things to do in Willoughby with kids?

    Families often enjoy exploring local parks, discovering hands-on exhibits at museums, or attending seasonal community events around Willoughby. Outdoor playgrounds and nearby nature centers frequently appeal to children of all ages.

  • What are some of the best things to do in Willoughby?

    Stroll through Willoughby’s downtown for local shops and cafes, explore community parks, or join in frequent arts events and seasonal celebrations. Many travelers appreciate its neighborhood festivals and easy access to nature.

  • How is the weather in Willoughby?

    Willoughby has cold winters, with temperatures from around 22°F to 36°F (-5°C to 2°C), and warm summers, usually reaching 65°F to 84°F (19°C to 29°C). Rain and snowfall can be expected throughout the year, so packing layers and a rain jacket is helpful.

  • When is the best time to visit Willoughby?

    Late spring through early fall is often recommended, when temperatures are mild and local events fill the calendar. Blossoming parks and outdoor activities tend to be popular during this period.

  • What are the best places to visit in Willoughby?

    Explore Willoughby’s historic downtown district, which has local boutiques and dining, or discover the Willoughby Area Welcome Center for regional history. Area parks and art galleries also provide engaging experiences for a variety of interests.

  • What are some hiking trails in Willoughby?

    Willoughby has walking paths and nature trails in area parks, where you can explore wooded landscapes and observe local wildlife. Trails with gentle terrain are frequently suggested for families and casual hikers.

  • What are some family activities we can do in Willoughby?

    Families can explore interactive exhibits at museums, play in local parks, or enjoy seasonal farmers markets and outdoor concerts. Community event calendars often feature kid-friendly programming throughout the year.

  • What are some of the best day trip ideas from Willoughby?

    Many guests explore nearby Lake Erie beaches, wooded nature preserves, and local wineries. Cultural attractions in the surrounding region, such as museums or scenic gardens, are also frequently suggested for day trips.

  • Are there any pet friendly accommodations available in Willoughby?

    Willoughby has a selection of pet-friendly accommodations, with some vacation rentals and local lodging welcoming guests with pets. Parks and walking trails also make it comfortable for those traveling with animals.

  • What are some local tips for visiting Willoughby?

    Check local event calendars for street fairs and live music, as Willoughby often has community happenings throughout the year. Enjoy walking around historic downtown, and try visiting local markets for regional treats and crafts.

  • What is Willoughby known for?

    Willoughby is known for its historic downtown, community-driven festivals, and welcoming small-town atmosphere. Its blend of preserved architecture and local art gives the city a strong sense of place.

  • What are the best hidden gems to explore in Willoughby?

    Around Willoughby, visitors enjoy uncovering public art murals, independent galleries, and small family-run shops tucked among residential streets. Quiet green spaces and community gardens often delight those looking for a peaceful retreat.

  • What are the best foods to try in Willoughby?

    Willoughby’s dining scene features classic American comfort foods, locally roasted coffee, and inventive sandwiches. Many visitors also enjoy locally owned bakeries and restaurants featuring seasonal dishes and fresh produce.

  • What should I bring for a trip to Willoughby?

    Pack layers to adjust to changing temperatures, comfortable walking shoes for exploring downtown and parks, and a rain jacket as weather patterns can shift. A camera is helpful for capturing local history and seasonal celebrations.

  • What is the nightlife in Willoughby like?

    Willoughby’s nightlife includes neighborhood bars, casual live music venues, and inviting wine bars often located in historic buildings. The downtown area is known for laid-back spots where guests can relax and connect with locals.

  • Are there family friendly vacation rentals in Willoughby?

    Willoughby has a range of vacation rentals that frequently welcome families, including entire homes and apartments with spacious living areas. Many listings provide amenities such as kitchens and outdoor space, making it comfortable for those traveling with children.

  • How much does it cost to stay in house rentals in Willoughby?

    Experience the best of Willoughby with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Quick stats about holiday rentals in Willoughby

  • Total holiday rentals

    Explore 60 holiday rentals in Willoughby

  • Nightly prices starting at

    Willoughby holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 3,490 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wifi availability

    60 of Willoughby holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Willoughby rentals

  • 4.8 Average rating

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

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  5. Willoughby