Willoughby Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Willoughby vacation rentals

Property grounds
Old Orchard Kirtland, Ohio

Vacation 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 ￥34,313
￥47,570 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Old Orchard Kirtland, Ohio
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 ￥22,824
￥25,952 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far
Outdoor dining
Crisp 2 bedroom upstairs apartment in historic duplex

Vacation 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 ￥15,285
￥23,526 total
includes taxes & fees
Jan 24 - Jan 25, 2026
Crisp 2 bedroom upstairs apartment in historic duplex
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 ￥22,824
￥25,952 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Lovely Lakewood:November Special 15% Off 4+ Nights

Vacation Home in Lakewood

Lovely Lakewood:November Special 15% Off 4+ Nights
9.2 out of 10, Wonderful, (81)
"Lovely stay!! "
United States
LISA
The price is ￥10,900
￥26,538 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Lovely Lakewood:November Special 15% Off 4+ Nights
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 ￥9,226
￥24,131 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Nice Apartment next to Christmas Story House
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)
"Very nice stay,just as described !!"
United States
Christine K.
The price is ￥13,370
￥21,189 total
includes taxes & fees
Jan 7 - Jan 8, 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 ￥13,433
￥29,787 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Historic District 1BR on 3rd Floor near Cleveland Clinic ~ Quiet & Safe
Fridge, microwave, oven, stovetop
Victorian Studio Steps from Cleveland Clinic

Vacation Home in Hough

Victorian Studio Steps from Cleveland Clinic
10.0 out of 10, Exceptional, (1)
The price is ￥14,015
￥33,885 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Victorian Studio Steps from Cleveland Clinic
Exterior detail
Charming flat near Cleve Clinic/CWRU/UH - in Larchmere w/Porch

Vacation Home in Buckeye-Shaker

Charming flat near Cleve Clinic/CWRU/UH - in Larchmere 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 traveler
The price is ￥11,259
￥24,895 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Charming flat near Cleve Clinic/CWRU/UH - in Larchmere w/Porch
Private kitchen
Modern Loft in Historic Birdtown - Unit 7

Apartment in Lakewood

Modern Loft in Historic Birdtown - Unit 7
2.0 star property
10.0 out of 10, Exceptional, (1)
"I rented this property for easy access to Mahalls for a concert. The concert got postponed unfortunstrly but the loft is a beautiful property. Has everything you would need for a one night stay. I did not stay overnight due to the concert being postponed but will be back for the show in october. Hosts are great to work with and very kind and quick to respond. Highly reccomend! "
United States
Sierra P.
The price is ￥18,062
￥33,112 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Modern Loft in Historic Birdtown - Unit 7
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 ￥29,478
￥52,406 total
includes taxes & fees
Jan 1 - Jan 2, 2026
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)
"Wonderful parking. Very nice kitchen. A very comfortable place to stay."
United States
Regina L.
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 ￥14,669
￥25,228 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Residential Apartment w/Drumkit
Fridge, microwave, oven, stovetop
Luxury Downtown Townhome w/ Private Garage Unit 14

Vacation Home in Downtown Cleveland

Luxury Downtown Townhome w/ Private Garage Unit 14
9.6 out of 10, Exceptional, (38)
"Great alternative to a hotel "
United States
Chuck A.
The price is ￥7,037
￥26,139 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Luxury Downtown Townhome w/ Private Garage Unit 14
Dining
Upscale suite in Lakewood

Apartment in Lakewood

Upscale suite in Lakewood
9.4 out of 10, Exceptional, (10)
"Great clean property, good responses & check in from owner and lots of entertainment, food nearby."
United States
jim n.
The price is ￥9,202
￥24,068 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Upscale suite in Lakewood
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 ￥12,478
￥28,075 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Casual CLE: 10% off 2+ Nights + free late checkout
Interior
Tranquil Tremont-Stay 4 nights & Enjoy 25% off 5th night

Apartment in Tremont

Tranquil Tremont-Stay 4 nights & Enjoy 25% off 5th night
8.8 out of 10, Excellent, (13)
"Very nice place. Easy acces and parking."
Canada
Jessica D.
The price is ￥10,949
￥25,766 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Tranquil Tremont-Stay 4 nights & Enjoy 25% off 5th night
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.
Pine Lake Trout Club Cabin #1!!!
Interior
Modern 1B1.5B Loft w/ Gym + Parking

Apartment in University Circle

Modern 1B1.5B Loft w/ Gym + Parking
10.0 out of 10, Exceptional, (4)
"This places was great! Very clean and comfortable and Dallas and Mari were excellent. Will definitely stay again."
United States
Cynthia
The price is ￥14,489
￥34,062 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Modern 1B1.5B Loft w/ Gym + Parking
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.
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Top Willoughby Hotel Reviews

Hilton Cleveland Downtown

Hilton Cleveland Downtown

10/10 Excellent
"Great Family Stay"
Moises 1-night trip
Posted 1 day ago
Hilton Cleveland Downtown

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 vacation rentals in Willoughby?

Yes, we have vacation rentals in Willoughby near The Holden Arboretum, or you can choose a more remote option if you'd like a relaxing place to 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 vacation rentals that Willoughby has to offer?

Luxury Downtown Townhome w/ Private Garage Unit 4: This vacation 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 vacation rentals are there in Willoughby?

Expedia has 16 vacation rentals for your stay in Willoughby.

What can I see and do in Willoughby?

Chagrin River and The Holden Arboretum 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 Lake Erie and North Chagrin Reservation.

What are vacation rentals like in Willoughby?

Vacation rentals are privately owned accommodations you can book for several days or more in Willoughby. Vacation rentals provide amenities such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a family trip.