Photo by throwingsofas

Willoughby Hills Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Willoughby Hills

Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Burton
10.0 out of 10, Exceptional, (48)
"I have stayed here before and enjoyed it just as much the second time. The place had a lot of charm, was very clean and was very convenient to where I was working. I will stay there again. "
United States
Kathryn
The price is AU$165
includes taxes & fees
8 Dec - 9 Dec
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Crisp 2 bedroom upstairs apartment in historic duplex

Stockyards
10.0 out of 10, Exceptional, (46)
"Had a great stay here while in Cleveland for a concert. Clean, comfortable, and great location. Would definitely stay again if in the area! "
United States
Ashley F.
The price is AU$231
includes taxes & fees
7 Dec - 8 Dec
Crisp 2 bedroom upstairs apartment in historic duplex

Coastal Lake Erie Cottage w/ Amazing Water Views!

3.0 star property
Euclid
The price is AU$282
includes taxes & fees
7 Dec - 8 Dec
Coastal Lake Erie Cottage w/ Amazing Water Views!

Victorian Studio Steps from Cleveland Clinic

Hough
10.0 out of 10, Exceptional, (1)
The price is AU$336
includes taxes & fees
7 Dec - 8 Dec
Victorian Studio Steps from Cleveland Clinic

Residential Apartment w/Drumkit

Willowick
10.0 out of 10, Exceptional, (18)
"Very clean and host was attentive."
United States
Amanda
The price is AU$248
includes taxes & fees
7 Dec - 8 Dec
Residential Apartment w/Drumkit

Country Cottage Farm Stay at Stoneycreek Acres

Newbury
10.0 out of 10, Exceptional, (70)
"Loved our stay!! Clean and wonderful! "
United States
Amber S.
The price is AU$504
includes taxes & fees
21 Dec - 22 Dec
Country Cottage Farm Stay at Stoneycreek Acres

Nice Apartment next to Christmas Story House

Tremont
9.8 out of 10, Exceptional, (24)
"We absolutely loved this place ! "
United States
Celeste K.
The price is AU$207
includes taxes & fees
5 Jan - 6 Jan 2026
Nice Apartment next to Christmas Story House

Little Italy Gem: Close to CWRU, Cleveland Clinic & Top Restaurants w/ King Bed

University Circle
9.6 out of 10, Exceptional, (13)
"Hosts were super responsive and helpful all along the way. Great stay."
United States
Laurel H.
Little Italy Gem: Close to CWRU, Cleveland Clinic & Top Restaurants w/ King Bed

Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Buckeye-Shaker
9.8 out of 10, Exceptional, (57)
"We had made a prior request that housekeeping avoid scented cleaning products as much as possible (due to allergies and sensitivities of people in our group). We were very pleased with their efforts, and our stay was allergy-free! Also, the host, Ken Love, was very responsive when I had questions/comments during and after our stay."
United States
Patricia
The price is AU$244
includes taxes & fees
7 Dec - 8 Dec
Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Casual CLE: 10% off 2+ Nights + free late checkout

Tremont
8.8 out of 10, Excellent, (10)
"Great little comfortable spot. Host was very responsive and helpful. Highly recommend. "
United States
Erin
The price is AU$275
includes taxes & fees
4 Jan - 5 Jan 2026
Casual CLE: 10% off 2+ Nights + free late checkout

Lovely Lakewood:November Special 15% Off 4+ Nights

Lakewood
9.2 out of 10, Wonderful, (81)
"It was a nice place. We would stay again. "
United States
Misty F.
The price is AU$291
includes taxes & fees
4 Jan - 5 Jan 2026
Lovely Lakewood:November Special 15% Off 4+ Nights

Historic District 2BR on 1st Floor near Cleveland Clinic ~ Family Friendly ~Safe

Shaker Heights
9.8 out of 10, Exceptional, (8)
"We stayed here during a family member’s medical procedure. It is located on a quiet, safe neighborhood, convenient to restaurants and shops. The first floor unit was comfortable and had everything we needed. "
United States
Natalie S.
Historic District 2BR on 1st Floor near Cleveland Clinic ~ Family Friendly ~Safe

Luxury Downtown Townhome w/ Private Garage Unit 11

Downtown Cleveland
10.0 out of 10, Exceptional, (15)
"My family and I stayed there recently for a concert. Great place, clean, good location, excellent communication with the owner! Would definitely stay again!"
United States
Marla A.
The price is AU$264
includes taxes & fees
16 Dec - 17 Dec
Luxury Downtown Townhome w/ Private Garage Unit 11

Pine Lake Trout Club Cabin #1!!!

Chagrin Falls
10.0 out of 10, Exceptional, (2)
"Nice area, very accommodating, Thanks ! "
United States
Dana d.
The price is AU$306
includes taxes & fees
21 Dec - 22 Dec
Pine Lake Trout Club Cabin #1!!!

Upscale suite in Lakewood

Lakewood
9.4 out of 10, Exceptional, (9)
"Great clean property, good responses & check in from owner and lots of entertainment, food nearby."
United States
jim n.
The price is AU$210
includes taxes & fees
11 Dec - 12 Dec
Upscale suite in Lakewood

2 Queen Beds in 1896 Victorian Triplex! AC, WiFi, Parking & More!

2.0 star property
Lakewood
7.6 out of 10, Good, (14)
"Good communication with the owner. Parking is poor . That area needs cleaned up. Everything about the apartment was nice. Bed was comfortable. "
United States
Shirley M.
The price is AU$293
includes taxes & fees
6 Dec - 7 Dec
2 Queen Beds in 1896 Victorian Triplex! AC, WiFi, Parking & More!

Charming studio apartment in fantastic Cleveland Tremont area

2.0 star property
Tremont
10.0 out of 10, Exceptional, (3)
"it was beautiful apartment, very clean, host Derrick was very helpful, he responded to our text messages immediately. "
United States
Savitha C.
The price is AU$174
includes taxes & fees
1 Jan - 2 Jan 2026
Charming studio apartment in fantastic Cleveland Tremont area

Sunfish Room

2.0 star property
Fairport Harbor
9.0 out of 10, Wonderful, (17)
"This property was accurate to description, walking distance to Fairport beach park, cute little downtown, close to Headlands Beach, dinner at Pickle Bills is a must. We will stay again. "
United States
Jennifer E.
The price is AU$260
includes taxes & fees
6 Dec - 7 Dec
Sunfish Room

Welcome to the Sandcastle Suite

Fairport Harbor
10.0 out of 10, Exceptional, (27)
"Within walking distance from the concert venue by the water. Clean and quiet apartment perfect for what we needed. Good communication from the host with necessary details. "
United States
Anonymous traveller
The price is AU$204
includes taxes & fees
1 Jan - 2 Jan 2026
Welcome to the Sandcastle Suite

Tranquil Tremont-Stay 4 nights & Enjoy 25% off 5th night

Tremont
8.8 out of 10, Excellent, (13)
"Great location in a very walkable area of Cleveland. Nicely updated unit. "
United States
lisa
The price is AU$268
includes taxes & fees
11 Dec - 12 Dec
Tranquil Tremont-Stay 4 nights & Enjoy 25% off 5th night
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Willoughby Hills Hotel Reviews

Find out more about Willoughby Hills

Everything you need to know about Willoughby Hills holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Willoughby Hills holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Willoughby Hills holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Willoughby Hills holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Willoughby Hills. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Willoughby Hills holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Willoughby Hills holiday rentals we have selected for you start as low as AU$174 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Willoughby Hills rentals

At Expedia, we put the best Willoughby Hills holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Willoughby Hills rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Willoughby Hills holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Willoughby Hills. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Willoughby Hills?

Yes, there are holiday rentals close to the most popular sights in Willoughby Hills, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Willoughby Hills has to offer?

Luxury Downtown Townhome w/ Private Garage Unit 13: This holiday home rental outside of Willoughby Hills is equipped with a balcony, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Willoughby Hills?

North Chagrin Reservation and Chagrin River are a couple of lovely local spots to get outside and enjoy nature. Historic Kirtland and The Holden Arboretum are a couple of places you'll find in the wider area.

What are holiday rentals like in Willoughby Hills?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Willoughby Hills. Holiday rentals feature extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a family trip.