Willoughby Vacation Rentals

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Our top choices for Willoughby vacation rentals

Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far

Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far
Madison
9.4 out of 10, Exceptional, (6 reviews)
"Super clean and cozy cabin! I can’t wait to stay again! "
United States
Alyssa T.
The price is CA $227
CA $257 total
includes taxes & fees
May 3 - May 4
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far

Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat

Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
Madison
9.6 out of 10, Exceptional, (4 reviews)
"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 CA $227
CA $257 total
includes taxes & fees
May 4 - May 5
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat

Steps to Cleveland Clinic - Bright Studio

Steps to Cleveland Clinic - Bright Studio
Hough
10.0 out of 10, Exceptional, (2 reviews)
"host was very nice and attentive !"
United States
Trinity D.
The price is CA $115
CA $291 total
includes taxes & fees
May 5 - May 6
Steps to Cleveland Clinic - Bright Studio

Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch

Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch
Buckeye-Shaker
9.8 out of 10, Exceptional, (73 reviews)
"Great location for a Cleveland visit. Host was responsive and helpful. Will definitely stay again."
United States
Kathleen R.
The price is CA $98
CA $224 total
includes taxes & fees
May 4 - May 5
Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch

The View! Hot Tub-Golf Cart-Beaches-Billiards-King-Cottage Retreat Full of Fun

The View! Hot Tub-Golf Cart-Beaches-Billiards-King-Cottage Retreat Full of Fun
Fairport Harbor
10.0 out of 10, Exceptional, (61 reviews)
"Efficient booking, entry, and exit- The space was very clean and thoughtfully staged for a visit. We had a wonderful stay!"
United States
Kimberly P.
The price is CA $265
CA $531 total
includes taxes & fees
May 4 - May 5
The View! Hot Tub-Golf Cart-Beaches-Billiards-King-Cottage Retreat Full of Fun

Eclectic Stay in Waterloo Arts District

Eclectic Stay in Waterloo Arts District
North Shore Collinwood
9.8 out of 10, Exceptional, (12 reviews)
"Very unique place! It was like sleeping in a gallery!"
United States
Leah
The price is CA $122
CA $249 total
includes taxes & fees
May 3 - May 4
Eclectic Stay in Waterloo Arts District

Comfy Updated Historic Gem Pets OK 3B Vibrant Area

Comfy Updated Historic Gem Pets OK 3B Vibrant Area
Painesville
9.8 out of 10, Exceptional, (73 reviews)
"This location was perfect for our stay while visiting with family during the Christmas season. The host was very responsive and helpful. This location definitely had a home away from home feeling as we felt a warm welcome upon entering the home. "
United States
Patrick T.
The price is CA $149
CA $385 total
includes taxes & fees
May 5 - May 6
Comfy Updated Historic Gem Pets OK 3B Vibrant Area

Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Burton
10.0 out of 10, Exceptional, (60 reviews)
"We loved this little place. "
United States
Rolanda R.
The price is CA $141
CA $215 total
includes taxes & fees
May 4 - May 5
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Lovely near Cleve Clinic/CWRU/UH - in Larchmere w/Porch!

Lovely near Cleve Clinic/CWRU/UH - in Larchmere w/Porch!
Buckeye-Shaker
9.4 out of 10, Exceptional, (85 reviews)
"The house is clean the host is always present whenever you needed I enjoyed my stay I can recommend you to book your stay"
United States
TULINAYO T.
The price is CA $98
CA $216 total
includes taxes & fees
May 3 - May 4
Lovely near Cleve Clinic/CWRU/UH - in Larchmere w/Porch!

Beautiful cabin situated on wooded land with nice yard clearing and small stream

Beautiful cabin situated on wooded land with nice yard clearing and small stream
Madison
10.0 out of 10, Exceptional, (11 reviews)
"The location was very peaceful and relaxing. We felt at home with nature and enjoyed our time very much!"
United States
Steven B.
The price is CA $177
CA $229 total
includes taxes & fees
May 15 - May 16
Beautiful cabin situated on wooded land with nice yard clearing and small stream

Acadia Farms Carriage House

Acadia Farms Carriage House
Northfield
9.6 out of 10, Exceptional, (5 reviews)
"Clean room, beautiful grounds, well equipped kitchen, great location for dog walks! Perfect for our family of four!"
United States
Natalie
The price is CA $157
CA $271 total
includes taxes & fees
May 4 - May 5
Acadia Farms Carriage House

The House Hotels - Superior Road

The House Hotels - Superior Road
Cleveland Heights
9.4 out of 10, Exceptional, (21 reviews)
"A beautiful, comfortable, well kept apartment in a great location. This was ous second stay here so you know we like it!"
United States
Steve W.
The price is CA $150
CA $300 total
includes taxes & fees
May 5 - May 6
The House Hotels - Superior Road

Pine Lake Trout Club Cabin #8!!!

Pine Lake Trout Club Cabin #8!!!
Chagrin Falls
8.8 out of 10, Excellent, (12 reviews)
"I always love staying here! "
United States
Jade R.
The price is CA $231
CA $262 total
includes taxes & fees
May 3 - May 4
Pine Lake Trout Club Cabin #8!!!

Coastal Lake Erie Cottage w/ Amazing Water Views!

Coastal Lake Erie Cottage w/ Amazing Water Views!
3.0 star property
Euclid
The price is CA $111
CA $333 total
includes taxes & fees
May 4 - May 5
Coastal Lake Erie Cottage w/ Amazing Water Views!

Charming Duplex Near Shaker Square Cleveland

Charming Duplex Near Shaker Square Cleveland
Buckeye-Shaker
9.8 out of 10, Exceptional, (7 reviews)
"It is a clean, well maintained property. It was very comfortable & it is in a nice neighborhood."
United States
Julie S.
The price is CA $137
CA $403 total
includes taxes & fees
May 4 - May 5
Charming Duplex Near Shaker Square Cleveland

Lovely Lakewood:November Special 15% Off 3+ Nights

Lovely Lakewood:November Special 15% Off 3+ Nights
Lakewood
9.0 out of 10, Wonderful, (88 reviews)
"Perfect location for our needs. "
United States
Tracy S.
The price is CA $100
CA $237 total
includes taxes & fees
May 3 - May 4
Lovely Lakewood:November Special 15% Off 3+ Nights

Timeless Tremont- Enjoy 20% off 5+ nights

Timeless Tremont- Enjoy 20% off 5+ nights
Tremont
9.2 out of 10, Wonderful, (45 reviews)
"excellent property in a wonderful neighborhood, close to downtown "
United States
James
The price is CA $110
CA $255 total
includes taxes & fees
May 4 - May 5
Timeless Tremont- Enjoy 20% off 5+ nights

Nice Apartment next to Christmas Story House

Nice Apartment next to Christmas Story House
Tremont
9.8 out of 10, Exceptional, (27 reviews)
"Location was close to our activities "
United States
Brenda R.
The price is CA $80
CA $210 total
includes taxes & fees
May 10 - May 11
Nice Apartment next to Christmas Story House

Cozy studio near Cleve Clinic, Case

Cozy studio near Cleve Clinic, Case
Cleveland Heights
9.6 out of 10, Exceptional, (5 reviews)
"Very responsive host, nice and convenient area"
United States
Shannon
The price is CA $73
CA $216 total
includes taxes & fees
May 7 - May 8
Cozy studio near Cleve Clinic, Case

Tranquil Tremont-Stay 3 nights & Enjoy 25% off 4th night

Tranquil Tremont-Stay 3 nights & Enjoy 25% off 4th night
Tremont
9.2 out of 10, Wonderful, (18 reviews)
"Very nice place. Easy acces and parking."
Canada
Jessica D.
The price is CA $120
CA $253 total
includes taxes & fees
May 3 - May 4
Tranquil Tremont-Stay 3 nights & Enjoy 25% off 4th 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.
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Top Willoughby Hotel Reviews

Find out more about Willoughby

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Willoughby. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 14 vacation 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 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.