Photo by Kristin DePlatchett

Search Cottages in Chesterland

Compare 40 Cottages in Chesterland with updated reviews, rates, and availability.

RIVERFRONT Cottage-Hot Tub, Billiards, Golf Cart, Pet Friendly
Terrace/patio
RIVERFRONT Cottage-Hot Tub, Billiards, Golf Cart, Pet Friendly
10.0 out of 10, Exceptional, (35)
"Beautiful home great restaurants and nice accommodations very close to beach "
The price is SAR 657
SAR 1,374 total
includes taxes & fees
6 Nov - 7 Nov
RIVERFRONT Cottage-Hot Tub, Billiards, Golf Cart, Pet Friendly
Willow Woods Retreat | Farmhouse | Nature
Welcome to Willow Woods Retreat! Located in beautiful Kirtland, Ohio! We cannot wait to host you!
Willow Woods Retreat | Farmhouse | Nature
9.6 out of 10, Exceptional, (16)
"This property is a peaceful and quiet get away. We stayed for a week for a wedding and enjoyed the numerous parks nearby during our down time. Would definitely recommend."
Willow Woods Retreat | Farmhouse | Nature
Newly remodeled cozy cottage retreat
Kitchen with banquette dining.
Newly remodeled cozy cottage retreat
9.2 out of 10, Wonderful, (15)
"We had a nice stay at Jezira's Hidaway. The bed was comfortable, the kitchen was nice and the shower in the tiny bathroom was great! Everything was very clean."
Newly remodeled cozy cottage retreat
Vineyard View | Walk to Wineries & River| Hot Tub
Relax in the hot tub while gazing at the woodlands (you may see deer, fox and eagles!)
Vineyard View | Walk to Wineries & River| Hot Tub
10.0 out of 10, Exceptional, (54)
"We stayed for a weekend to visit the local wineries. We spent the first night in the hot tub and enjoyed every minute. The following day we went to a few wineries and went back to the house and walked to Laurentia across the street. The house is very, very nice. Very clean and accommodating. The house has everything you would need from shampoo/conditioner/soap, towels, linens, spices, etc. The view across from the house is breathtaking. We had an issue the first night with the hot tub and I...
The price is SAR 1,737
SAR 2,424 total
includes taxes & fees
10 Nov - 11 Nov
Vineyard View | Walk to Wineries & River| Hot Tub
Coastal Lake Erie Cottage w/ Amazing Water Views!
Euclid Vacation Rental | 4BR | 2BA | Stairs Required | 2,000 Sq Ft
Coastal Lake Erie Cottage w/ Amazing Water Views!
9.8 out of 10, Exceptional, (6)
"Amazing property with spectacular views! The owner is amazing to work with and very communicative."
Coastal Lake Erie Cottage w/ Amazing Water Views!
Modern Northfield Cottage w/ Yard!
Northfield Vacation Rental | 2BR | 1BA | 900 Sq Ft | Stairs Required
Modern Northfield Cottage w/ Yard!
8.4 out of 10, Very Good, (6)
"Perfect location to visit Cuyahoga National Park, Rock n Roll Hall of Fame and National Football League Hall of Fame. Located in a very quiet neighborhood."
Modern Northfield Cottage w/ Yard!
Luxurious 3-BR Lakefront Cottage on Lake Erie - Book Your Lakeside Retreat Today
Back Deck with View of Lake Erie - Beauty in All Directions
Luxurious 3-BR Lakefront Cottage on Lake Erie - Book Your Lakeside Retreat Today
10.0 out of 10, Exceptional, (81)
"We had a wonderful stay in this beautiful home. Great location. We accidentally left something behind and Linda mailed it to us."
Luxurious 3-BR Lakefront Cottage on Lake Erie - Book Your Lakeside Retreat Today
Lydia's Lake Erie Cottage
Sit under the weeping willow and enjoy the view!
Lydia's Lake Erie Cottage
10.0 out of 10, Exceptional, (16)
"The house is easy to find, has a gorgeous view and includes everything you need for a great getaway. I took my Mom for her 79th birthday and we explored the town and the Arboretum (note - $20 per person) and hung out at the house to watch the sunsets. "
Lydia's Lake Erie Cottage
Historic Cleveland Heights Carriage House!
Historic Cleveland Heights Carriage House!
9.8 out of 10, Exceptional, (30)
"CWRU parents here for a visit. Finally a Cleveland vrbo i will absolutely return to! The host was so wonderful. The little house is a perfect layout. Our daughter ended up sleeping over to get a break from the dorms and for some homemade food. Great walking neighborhood and close enough to walk to the university. Very quiet and comfortable. "
The price is SAR 845
SAR 1,686 total
includes taxes & fees
6 Nov - 7 Nov
Historic Cleveland Heights Carriage House!
Charming Cleveland Home: 5 Mi to Downtown!
Living area
Charming Cleveland Home: 5 Mi to Downtown!
3.0 star property
Charming Cleveland Home: 5 Mi to Downtown!
~ 2 Mi to Downtown - Cozy Cleveland Unit
Exterior
~ 2 Mi to Downtown - Cozy Cleveland Unit
3.0 star property
~ 2 Mi to Downtown - Cozy Cleveland Unit
Chagrin Falls Home ~ 2 Mi to Town!
Living area
Chagrin Falls Home ~ 2 Mi to Town!
3.0 star property
10.0 out of 10, Exceptional, (1)
Chagrin Falls Home ~ 2 Mi to Town!
Loft Unplugged w/ Outdoor Space in Amish Country!
Exterior
Loft Unplugged w/ Outdoor Space in Amish Country!
2.0 star property
8.0 out of 10, Very Good, (2)
"The property was just beautiful!! The host and hostess was just amazing, so polite and friendly. The loft was everything I expected!! I made 2 blankets while I was there .. I didn’t use the electric!! Or battery light I saved it for my daughter and grandson for the last 2 days. And now I have not watched tv since I have been home. And I quit social media. I could live there. Please go stay !! Best thing ever !! "
Loft Unplugged w/ Outdoor Space in Amish Country!
Cozy Mosaic Cottage minutes from Lake Erie!
Property grounds
Cozy Mosaic Cottage minutes from Lake Erie!
10.0 out of 10, Exceptional, (5)
"This house was perfect for our first visit to Cleveland. Super quiet, friendly neighborhood, easy commute to the city, nice outdoor space. Our host provided snacks and everything else we needed to feel at home. Would highly recommended!"
Cozy Mosaic Cottage minutes from Lake Erie!
Central Cleveland Gem w/ Direct Skyline View!
Property grounds
Central Cleveland Gem w/ Direct Skyline View!
3.0 star property
Central Cleveland Gem w/ Direct Skyline View!
Modern Northfield Cottage w/ Yard!
Living area
Modern Northfield Cottage w/ Yard!
3.0 star property
Modern Northfield Cottage w/ Yard!
Cleveland Heights Retreat: Close to Everything!
Living area
Cleveland Heights Retreat: Close to Everything!
3.0 star property
Cleveland Heights Retreat: Close to Everything!
Lakefront cottage with amazing views
Outdoor dining
Lakefront cottage with amazing views
10.0 out of 10, Exceptional, (5)
"Lovely and relaxing, had some stunning sunsets and even saw a beautiful rainbow. Easy to travel to the Rock and Roll HOF, all the museums, and the zoo! Great truly lakefront getaway! "
Lakefront cottage with amazing views
Lakefront Burton Home w/ Deck, Grill + Views!
Burton Vacation Rental | 2BR | 1BA | 1,000 Sq Ft | 10 Stairs Required to Enter
Lakefront Burton Home w/ Deck, Grill + Views!
10.0 out of 10, Exceptional, (2)
"Peaceful and serene. Enjoyed every minute."
Lakefront Burton Home w/ Deck, Grill + Views!
Pet-friendly Home - 1/2 Mi to Downtown Willoughby!
Property grounds
Pet-friendly Home - 1/2 Mi to Downtown Willoughby!
3.0 star property
10.0 out of 10, Exceptional, (1)
"This house was exactly what we needed for our stay last weekend. Looks newly renovated and is well appointed with dishes, wine glasses, etc. Very comfortable and sparkling clean. Would definitely stay again. "
Pet-friendly Home - 1/2 Mi to Downtown Willoughby!
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.
Don't see what you're looking for?
See all available properties in Chesterland
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chesterland

The Abbey Apartments By Barsala
Exterior
The Abbey Apartments By Barsala
4.0 star property
8.4 out of 10, Very Good, (65)
"I would highly recommend. The building was incredible. Almost brand new, beautiful and clean. The check in and out process was easy and flawless and the location was convenient to everything you would with to do in downtown. I will definitely be staying here again when I am back in Cleveland. "
The Abbey Apartments By Barsala
CLE BNB Getaway ★ 15 Guests ★ Stunning Kitchen ★ Game Room ★ Big Fenced Yard
Living area
CLE BNB Getaway ★ 15 Guests ★ Stunning Kitchen ★ Game Room ★ Big Fenced Yard
8.8 out of 10, Excellent, (67)
"It went well and was beyond what we expected."
The price is SAR 323
SAR 1,108 total
includes taxes & fees
11 Nov - 12 Nov
CLE BNB Getaway ★ 15 Guests ★ Stunning Kitchen ★ Game Room ★ Big Fenced Yard
Relaxing Downtown Apartment
Point of interest
Relaxing Downtown Apartment
7.8 out of 10, Good, (14)
"This unit suited our needs for an enjoyable weekend stay in Cleveland to check out a couple baseball games and RRHOF. Host was responsive and timely in responses. Location is in the University area about a 15-20 min walk from downtown core. Unit was clean and as described in the ad. Safe above ground parking provided that has in-out access. Re: the odor noted by others: there is a deodorizer continuously circulated into the hallways of the building but I didn’t find it overly noticeable or...
The price is SAR 300
SAR 739 total
includes taxes & fees
7 Nov - 8 Nov
Relaxing Downtown Apartment
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.

Frequently asked questions

Why book your cottage in Chesterland with Expedia?
Expedia has some great cottages in Chesterland, so get set for an unforgettable vacation on nature’s doorstep. If you have a set budget, select how much you want to spend and the star rating of your property. Or, make your way to the filters to search for cottages with a hot tub or a kitchen. We’ll help you find the perfect digs whatever your getaway looks like.
How can I find cheap cottages in Chesterland?
Expedia can help you easily locate cheap cottages in Chesterland. To lock in a fantastic stay in just a few keystrokes, use the filter tool to refine your search by amenities, budget and star rating.