Willoughby 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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Willoughby holiday rentals

Property grounds
Old Orchard Kirtland, Ohio

Holiday Home in Waite Hill

Old Orchard Kirtland, Ohio
9.8 out of 10, Exceptional, (7)
"Wonderful hospitality!! Very clean. Great owners!!"
United States
Christa K.
The price is HK$1,711
HK$2,372 total
includes taxes & fees
31 Dec - 1 Jan 2026
Old Orchard Kirtland, Ohio
Outdoor dining
Crisp 2 bedroom upstairs apartment in historic duplex

Holiday Home in Stockyards

Crisp 2 bedroom upstairs apartment in historic duplex
10.0 out of 10, Exceptional, (47)
"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 HK$762
HK$1,173 total
includes taxes & fees
29 Dec - 30 Dec
Crisp 2 bedroom upstairs apartment in historic duplex
Dining
Country Cottage Farm Stay at Stoneycreek Acres

Cottage in Newbury

Country Cottage Farm Stay at Stoneycreek Acres
10.0 out of 10, Exceptional, (70)
"An absolutely delightful stay for me, my mother and my daughter. The host and her family were so gracious when we asked to be seen around the farm! I don’t know what was better, the adorable cottage or the hospitality they showed us. Will definitely be staying here again!!"
United States
Christine D.
The price is HK$1,470
HK$2,613 total
includes taxes & fees
30 Dec - 31 Dec
Country Cottage Farm Stay at Stoneycreek Acres
Dining
Historic Cleveland Heights Carriage House!

Cottage in Cleveland Heights

Historic Cleveland Heights Carriage House!
9.4 out of 10, Exceptional, (44)
"AMAZING rental! Great location, beautifully decorated, wonderful host! It had everything we needed and everything was on one level with only 2 steps to enter! Thank yo Kristen; you have a beautiful property!"
United States
Anonymous traveller
The price is HK$1,244
HK$2,833 total
includes taxes & fees
7 Jan - 8 Jan 2026
Historic Cleveland Heights Carriage House!
Property grounds
Residential Apartment w/Drumkit

Apartment in Willowick

Residential Apartment w/Drumkit
10.0 out of 10, Exceptional, (18)
"Cute apartment in a quiet neighborhood!"
United States
Shainna P.
The price is HK$731
HK$1,258 total
includes taxes & fees
28 Dec - 29 Dec
Residential Apartment w/Drumkit
Fridge, microwave, oven, stovetop
Victorian Studio Steps from Cleveland Clinic

Holiday Home in Hough

Victorian Studio Steps from Cleveland Clinic
10.0 out of 10, Exceptional, (1)
The price is HK$697
HK$1,685 total
includes taxes & fees
28 Dec - 29 Dec
Victorian Studio Steps from Cleveland Clinic
Fridge, microwave, oven, stovetop
Center of Little Italy #1

Apartment in University Circle

Center of Little Italy #1
9.6 out of 10, Exceptional, (16)
"Great location! Super cute place. Owner was very responsive and helpful. "
United States
Maria E.
The price is HK$653
HK$1,509 total
includes taxes & fees
26 Dec - 27 Dec
Center of Little Italy #1
Fridge, microwave, oven, stovetop
Casual CLE: 10% off 2+ Nights + free late checkout

Apartment in Tremont

Casual CLE: 10% off 2+ Nights + free late checkout
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 HK$622
HK$1,415 total
includes taxes & fees
5 Jan - 6 Jan 2026
Casual CLE: 10% off 2+ Nights + free late checkout
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Lovely Lakewood:November Special 15% Off 4+ Nights

Holiday Home in Lakewood

Lovely Lakewood:November Special 15% Off 4+ Nights
9.2 out of 10, Wonderful, (81)
"It was a nice place. We would stay again. "
United States
Misty F.
The price is HK$542
HK$1,320 total
includes taxes & fees
2 Jan - 3 Jan 2026
Lovely Lakewood:November Special 15% Off 4+ Nights
Interior
Coastal Lake Erie Cottage w/ Amazing Water Views!

Cottage in Euclid

Coastal Lake Erie Cottage w/ Amazing Water Views!
3.0 star property
The price is HK$607
HK$1,620 total
includes taxes & fees
29 Dec - 30 Dec
Coastal Lake Erie Cottage w/ Amazing Water Views!
TV
Nice Apartment next to Christmas Story House

Apartment in Tremont

Nice Apartment next to Christmas Story House
9.8 out of 10, Exceptional, (25)
"We absolutely loved this place ! "
United States
Celeste K.
The price is HK$459
HK$1,200 total
includes taxes & fees
5 Jan - 6 Jan 2026
Nice Apartment next to Christmas Story House
Exterior detail
Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Holiday Home in Buckeye-Shaker

Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!
9.8 out of 10, Exceptional, (58)
"Great location. Host was very responsive. This unit is comfortable, well stocked and was perfect for our trip to Cleveland Clinic!"
United States
Anonymous traveller
The price is HK$560
HK$1,238 total
includes taxes & fees
30 Dec - 31 Dec
Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!
Smart TV
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Apartment in Burton

Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
10.0 out of 10, Exceptional, (50)
"Room was spotless, everything perfect"
United States
Marla
The price is HK$665
HK$1,054 total
includes taxes & fees
4 Jan - 5 Jan 2026
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Smart TV
Historic District 1BR on 3rd Floor near Cleveland Clinic ~ Quiet & Safe

Apartment in Shaker Heights

Historic District 1BR on 3rd Floor near Cleveland Clinic ~ Quiet & Safe
9.8 out of 10, Exceptional, (7)
"Clean, Unique, Safe/Quiet "
United States
Will P.
The price is HK$781
HK$1,625 total
includes taxes & fees
3 Jan - 4 Jan 2026
Historic District 1BR on 3rd Floor near Cleveland Clinic ~ Quiet & Safe
Outdoor spa tub
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far

Cabin in Madison

Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far
10.0 out of 10, Exceptional, (1)
"The property is amazing, as is the cabin. Love the decor. We appreciated the privacy, the hot tub worked great. We also appreciated the fire ring with everything needed to build a fire! We had a lovely visit with a great friend, daughter, and her grandson that live in the area. Thanks for everything!"
United States
Jeannie
The price is HK$1,788
HK$2,045 total
includes taxes & fees
31 Dec - 1 Jan 2026
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far
Microwave, oven, stovetop, dishwasher
Luxury Loft Getaway in Downtown Cleveland

Apartment in Downtown Cleveland

Luxury Loft Getaway in Downtown Cleveland
2.0 star property
10.0 out of 10, Exceptional, (1)
The price is HK$700
HK$1,011 total
includes taxes & fees
26 Dec - 27 Dec
Luxury Loft Getaway in Downtown Cleveland
Outdoor spa tub
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat

Cabin in Madison

Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
9.4 out of 10, Exceptional, (3)
"This was an incredible stay for my wife and I. The cleanliness, quietness, and coziness was amazing. We will definitely be back for another anniversary stay. The multiple wineries around also help enhance the stay even more. You’re missing out if you don’t book this cabin. "
United States
Matthew
The price is HK$1,625
HK$1,858 total
includes taxes & fees
26 Dec - 27 Dec
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
Fridge, microwave, oven, stovetop
Welcome to the Sandcastle Suite

Apartment in Fairport Harbor

Welcome to the Sandcastle Suite
10.0 out of 10, Exceptional, (27)
"I stayed here for business, but it felt like a mini vacation."
United States
Laura
The price is HK$995
HK$1,151 total
includes taxes & fees
26 Dec - 27 Dec
Welcome to the Sandcastle Suite
Interior
2-Story Downtown Townhome • FREE Parking • Gym

Apartment in Downtown Cleveland

2-Story Downtown Townhome • FREE Parking • Gym
10.0 out of 10, Exceptional, (2)
"Really nice place. "
Canada
Peter
2-Story Downtown Townhome • FREE Parking • Gym
Exterior
Pine Lake Trout Club Cabin #1!!!

Cabin in Chagrin Falls

Pine Lake Trout Club Cabin #1!!!
10.0 out of 10, Exceptional, (2)
"Nice area, very accommodating, Thanks ! "
United States
Dana d.
The price is HK$1,361
HK$1,555 total
includes taxes & fees
31 Dec - 1 Jan 2026
Pine Lake Trout Club Cabin #1!!!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Willoughby Hotel Reviews

Fidelity Hotel

Fidelity Hotel

10/10 Excellent
"The staff were super helpful and friendly. Everything was clean and beautifully decorated."
Krystina Del 4-night trip
Posted 19 hours ago
Fidelity Hotel

Find out more about Willoughby

Search for holiday rentals in Willoughby on Expedia! You can easily find your home rentals, villas, holiday apartments in Willoughby using one of the methods below:

  • View our selection of featured holiday rentals in Willoughby
  • Use the map to find apartments and other holiday homes in the Willoughby neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Willoughby while they last

Look no further and take a look at our great range of rental properties in Willoughby!

Frequently asked questions

Are there holiday rentals in Willoughby?

Yes, there are holiday rentals in Willoughby close to The Holden Arboretum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Willoughby. Make sure you have time to check out the temples and architecture during your trip.

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

Luxury Downtown Townhome w/ Private Garage Unit 13: This holiday home rental outside of Willoughby 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.

How many holiday rentals are there in Willoughby?

Expedia has 16 holiday rentals for your stay in Willoughby.

What can I see and do in Willoughby?

The Holden Arboretum and Lake Erie are a couple of scenic spots to enjoy the outdoors, whereas Historic Kirtland is one of the cultural attractions. Other places in town to visit include Chagrin River and North Chagrin Reservation.

What are holiday rentals like in Willoughby?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Willoughby. Holiday rentals provide amenities such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a small group gathering.