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Holiday rentals in Willoughby

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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 $52 SGD 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!

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
A welcoming entryway is seen, featuring a wooden console table with decorative items and candles. A framed photograph of palm trees hangs above. Light-colored walls reflect natural light, while a vibrant green plant complements the warm wood tones. A rug with a bold pattern adds subtle texture.
Home in Willoughby
4.98 out of 5 average rating, 53 reviews

Little Willow: cozy stay with minute drive to town

Charming Small Home with Crafted Details • 700 sq ft • 8-minute walk 2-minute drive to downtown’s welcoming shops, restaurants, and coffee spots. This thoughtfully curated space meets your every need and helps you unwind after your travels. Relax in open, comfortable seating, browse shelves filled with books, and enjoy streaming services ready for a cozy night in. With rolled face towels and a clean, cozy atmosphere, thoughtful touches throughout make you feel at home from the moment you arrive.

FamilyValueHospitality

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, 174 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.

FamilyLocationParking

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, 278 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

ValueFamilyOutdoor spaces

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, 334 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.

LocationValueAir conditioning

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, 548 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.

ValueLocationAmenities

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, 116 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.

LocationValueCondition

Guest favourite
A spacious living room is highlighted by a large sectional sofa adorned with decorative pillows and a cozy throw. A wooden coffee table is centered on a patterned area rug, while natural light fills the room through two partially draped windows.
Home in Eastlake
4.89 out of 5 average rating, 76 reviews

Charming Property Eastlake Ohio

Charming & comfortable ranch style property. Located in a convenient & peaceful neighborhood. Two very comfy bedrooms one with a king bed, large TV the 2nd bedroom has a queen bed, vanity or work space and bay window. Living room boasts a huge TV, fireplace with elegant furnishings. Fully equipped kitchen. Entire homes is totally renovated. Peaceful yard, patio, garage, and fire pit. Close to Downtown Cleveland, major hospitals, restaurants, shopping, parks & entertainment! Treat yourself!

LocationFamilyParking

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, 210 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.

LocationValueOutdoor spaces

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, 146 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.

FamilyValueLong stay

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, 114 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!

ValueLocationCheckout

Top guest favourite
Flat in Willoughby
4.96 out of 5 average rating, 136 reviews

The Nest! 2 bedroom

Welcome to our charming 2 bedroom 1 bathroom unit, where comfort meets convenience! Nestled within walking distance (.03miles) from Historic Downtown Willoughby, our stylish and spacious accommodation offers a delightful retreat for your stay. With thoughtful touches, modern amenities (Smart TV's, Keurig), and proximity to local attractions, such as dining, shopping, and the local nightlife! We guarantee a memorable experience during your time here.

FamilyValueLaundry

Superhost
A modern living area features a comfortable sectional sofa positioned near a glass coffee table. Natural light enters through two windows, and a potted plant adds a touch of greenery. The entrance door is visible, leading to the outside space.
Flat in Willoughby
4.59 out of 5 average rating, 358 reviews

1 BR WiFi Downtown Willoughby self check in Unit B

1BR Unit that is walking distance to Downtown Willoughby. Enjoy the added touches like smart TVs in the living room and bedroom. The bathroom is small so please take a look at the pictures. A kuerig coffee machine for that morning cup of coffee. A comfy pillow top mattress makes this location perfect for a quick getaway to enjoy the downtown willoughby area.

LocationValueHiking

Popular amenities for Willoughby holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Willoughby

Top guest favourite
Home in Eastlake
4.93 out of 5 average rating, 87 reviews

Relaxing Lakeside Getaway

FamilyValueCheck-in

Guest favourite
A cozy dining area is highlighted by a large claw-foot antique dining table, surrounded by contemporary seating. A prominent stone fireplace, framed by wooden paneling, adds character to the space. Bookshelves can be seen in the background, contributing to the rustic charm.
Cabin in Euclid
4.9 out of 5 average rating, 307 reviews

Century-plus Summer Cabin - The Perfect Getaway!

LocationFamilyIndoor spaces

Top guest favourite
The exterior of the historic carriage house is shown, featuring a brick facade and white trim. A covered gazebo with an American flag fluttering nearby is positioned in a landscaped area with blooming flowers and decorative stones, adding charm to the surroundings.
Guest house in Fairport Harbor
5 out of 5 average rating, 56 reviews

GrandVue - 1880 Carriage House

LocationValueIndoor spaces

Superhost
Home in Mentor
5 out of 5 average rating, 3 reviews

Central Mentor | 5 Beds | 2 Bath | Fenced Yard

LocationFamilySleep quality

Guest favourite
A cozy outdoor seating area features brown Adirondack chairs arranged around a circular gas firepit. In the foreground, a glass of red beverage is placed on a side table. The background captures a scenic sunset over Lake Erie, with hues of orange and purple reflecting on the water.
Cottage in Mentor-on-the-Lake
4.99 out of 5 average rating, 69 reviews

Relaxing 3BR Lakefront, Sunset Watching Paradise

ValueLocationOutdoor spaces

Top guest favourite
A vintage jukebox is displayed, featuring a vibrant red and pink pattern on its glass panels. The control panel showcases buttons for selecting music tracks, adding a nostalgic element to the entertainment space.
Home in Wickliffe
4.94 out of 5 average rating, 34 reviews

Cozy Retro Home-Close to All Activities in The CLE

ValueLocationSleep quality

Guest favourite
Home in Painesville
5 out of 5 average rating, 6 reviews

Golden Hour Retreat | Ranch /Sunroom-King Suite

LocationFamilyCleanliness

Top guest favourite
Home in Eastlake
4.96 out of 5 average rating, 49 reviews

Boho Vibes

LocationFamilyLong stay

When is the best time to visit Willoughby?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$167 SGD$171 SGD$168 SGD$167 SGD$167 SGD$168 SGD$187 SGD$185 SGD$181 SGD$181 SGD$193 SGD$202 SGD
Avg. temp-2°C0°C4°C10°C16°C21°C24°C23°C19°C13°C7°C1°C

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.

Destinations to explore

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