Photo by Kristin DePlatchett

Search Cottages in Chesterland

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Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

Compare 45 Cottages in Chesterland with updated reviews, rates, and availability.

Coastal Lake Erie Cottage w/ Amazing Water Views!
Property grounds

Coastal Lake Erie Cottage w/ Amazing Water Views!

10.0 out of 10, Exceptional, (16)
"Charming house and view. Very attentive host."
Coastal Lake Erie Cottage w/ Amazing Water Views!
Historic Cleveland Heights Carriage House!
Dining

Historic Cleveland Heights Carriage House!

9.6 out of 10, Exceptional, (33)
"This is our third time staying here and I highly recommend it!"
The price is SAR 769
SAR 1,586 total
includes taxes & fees
6 May - 7 May
Historic Cleveland Heights Carriage House!
Willow Woods Retreat - Farmhouse - Patio & Nature
Fridge, stovetop, dishwasher, coffee/tea maker

Willow Woods Retreat - Farmhouse - Patio & Nature

9.4 out of 10, Exceptional, (24)
"Overall,"
Willow Woods Retreat - Farmhouse - Patio & Nature
Luxurious 3-BR Lakefront Cottage on Lake Erie - Book Your Lakeside Retreat Today
Beach nearby, sun loungers, beach towels

Luxurious 3-BR Lakefront Cottage on Lake Erie - Book Your Lakeside Retreat Today

10.0 out of 10, Exceptional, (84)
"Clean, very comfortable and a great location. Would definitely stay again."
Luxurious 3-BR Lakefront Cottage on Lake Erie - Book Your Lakeside Retreat Today
Country Cottage Farm Stay at Stoneycreek Acres
Dining

Country Cottage Farm Stay at Stoneycreek Acres

9.8 out of 10, Exceptional, (60)
"It was a quaint and comfortable stay. We experienced no problems at all. Looking forward to returning soon. "
The price is SAR 596
SAR 1,135 total
includes taxes & fees
6 May - 7 May
Country Cottage Farm Stay at Stoneycreek Acres
Relax on Lake Erie at our charming 2-bedroom cottage
Property grounds

Relax on Lake Erie at our charming 2-bedroom cottage

10.0 out of 10, Exceptional, (16)
"Property was perfect for relaxation and visiting the area. Owner made sure we had everything we needed. Loved staying here"
Relax on Lake Erie at our charming 2-bedroom cottage
The View! Hot Tub-Golf Cart-Beaches-Billiards-King-Cottage Retreat Full of Fun
Beach nearby, sun loungers, beach towels

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

10.0 out of 10, Exceptional, (42)
"Work stay"
The price is SAR 938
SAR 1,729 total
includes taxes & fees
18 May - 19 May
The View! Hot Tub-Golf Cart-Beaches-Billiards-King-Cottage Retreat Full of Fun
Vineyard View | Walk to Wineries & River| Hot Tub
Terrace/patio

Vineyard View | Walk to Wineries & River| Hot Tub

10.0 out of 10, Exceptional, (58)
"Perfect house for the four of us and our dog. Great location and we will be back!"
The price is SAR 1,078
SAR 1,717 total
includes taxes & fees
8 May - 9 May
Vineyard View | Walk to Wineries & River| Hot Tub
Modern Northfield Cottage w/ Yard!
Coffee/tea maker, cookware/dishes/utensils

Modern Northfield Cottage w/ Yard!

8.4 out of 10, Very Good, (9)
"This was the perfect place to stay for a trip to see family over the holidays. The location is wonderful for the ships in Macedonia or accessibility to Cleveland and surrounding cities. The place itself was a great peaceful retreat after long days of visits with family. Highly recommend this property!"
Modern Northfield Cottage w/ Yard!
Lakeview Happy Days Cozy Cottage
Miscellaneous

Lakeview Happy Days Cozy Cottage

6.8 out of 10, (3)
"Cottage had been redone on the inside and was adequate for our needs. Horrible weather storm went through towards the end of our stay. The cottage lost power for a number of days making it impossible to continue the stay and we ended up in a hotel for 6 nights."
Lakeview Happy Days Cozy Cottage
4 Mi to Dtwn: Home w/ Patio in Cleveland!
Interior

4 Mi to Dtwn: Home w/ Patio in Cleveland!

3.0 star property
8.0 out of 10, Very Good, (1)
"Nice house. Decorated nicely. It is an old place (thinking circa 1900), so going upstairs was a chore. The stairs are extremely narrow and steep. They did a nice job of making us feel welcome. The area is industrial, there were a lot of trains throughout the night. We did feel safe staying there. It is in a great location when it comes to exploring Cleveland. Very close to everything. All in all, we had a good stay. "
4 Mi to Dtwn: Home w/ Patio in Cleveland!
University Heights Home Near Downtown Cleveland!
House (3 Bedrooms) | Private kitchen | Coffee/tea maker, paper towels

University Heights Home Near Downtown Cleveland!

3.0 star property
University Heights Home Near Downtown Cleveland!
Chagrin Falls Home ~ 2 Mi to Town!
Terrace/patio

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!
Game room

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!
Modern Northfield Cottage w/ Yard!
Cottage (2 Bedrooms) | Private kitchen | Paper towels

Modern Northfield Cottage w/ Yard!

3.0 star property
Modern Northfield Cottage w/ Yard!
Cozy Mosaic Cottage minutes from Lake Erie!
Point of interest

Cozy Mosaic Cottage minutes from Lake Erie!

10.0 out of 10, Exceptional, (5)
"Perfect spot for a week of Lake County baseball! Very comfortable and well appointed. Will stay again."
Cozy Mosaic Cottage minutes from Lake Erie!
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
Pet-friendly Home - 1/2 Mi to Downtown Willoughby!
Interior

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!
Newly remodeled cozy cottage retreat
Exterior

Newly remodeled cozy cottage retreat

9.4 out of 10, Exceptional, (18)
"Nice and clean little cottage. Stayed for 2 weeks over Thanksgiving 2024. Convenient to Rt. 2, Mentor, Cleve, etc. 10/10, no notes. "
Newly remodeled cozy cottage retreat
Large Yard & Fire Pit: Pet-friendly Ravenna Home!
Interior

Large Yard & Fire Pit: Pet-friendly Ravenna Home!

3.0 star property
8.0 out of 10, Very Good, (1)
Large Yard & Fire Pit: Pet-friendly Ravenna Home!
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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Other property types in Chesterland

2125 Superior Living
Interior

2125 Superior Living

2.0 star property
5.6 out of 10, (21)
"Great place, affordable, and close to attractions"
The price is SAR 251
SAR 670 total
includes taxes & fees
7 May - 8 May
2125 Superior Living
Barsala At The Monroe Apartments
Interior

Barsala At The Monroe Apartments

4.0 star property
9.0 out of 10, Wonderful, (30)
"Great place to stay, we loved walking to Little Italy. Accommodations were clean and quiet, would definitely stay again."
Barsala At The Monroe Apartments
The Abbey Apartments By Barsala
Exterior

The Abbey Apartments By Barsala

3.5 star property
8.6 out of 10, Excellent, (89)
"It was a really nice place to stay will be booking again "
The Abbey Apartments By Barsala
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.