Photo by Kristin DePlatchett

Search Cottages in Chesterland

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

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, (13)
"Love the older house feel . The view was amazing ,and the sound of the waves were very relaxing . The host was a pleasure to deal with and communicated well . Would definitely stay again "
Coastal Lake Erie Cottage w/ Amazing Water Views!
Historic Cleveland Heights Carriage House!
Dining

Historic Cleveland Heights Carriage House!

9.8 out of 10, Exceptional, (31)
"This is our third time staying here and I highly recommend it!"
The price is SAR 769
SAR 1,571 total
includes taxes & fees
30 Mar - 31 Mar
Historic Cleveland Heights Carriage House!
Willow Woods Retreat - Farmhouse - Patio & Nature
Fridge, stovetop, dishwasher, coffee/tea maker

Willow Woods Retreat - Farmhouse - Patio & Nature

9.2 out of 10, Wonderful, (22)
"Very nice stay. We enjoyed the house very much. Everything was very clean. The hot chocolate setup was a nice touch!"
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, (83)
"We are from Arkansas, but my son and 3 grandsons live in the Cleveland area. We got there in the evening and were delighted to see the home was completely decorated for Christmas. It is such a cozy home with a great kitchen, with a big dining table. It made for a wonderful celebration. "
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 4
SAR 450 total
includes taxes & fees
31 Mar - 1 Apr
Country Cottage Farm Stay at Stoneycreek Acres
Lydia's Lake Erie Cottage
Property grounds

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
RIVERFRONT Cottage-Hot Tub, Billiards, Golf Cart, Pet Friendly
Beach nearby, sun loungers, beach towels

RIVERFRONT Cottage-Hot Tub, Billiards, Golf Cart, Pet Friendly

10.0 out of 10, Exceptional, (41)
"Used as a central point for traveling family. Lots of room for kids including a basement to play. And it was decorated for Christmas! "
The price is SAR 807
SAR 1,549 total
includes taxes & fees
21 Apr - 22 Apr
RIVERFRONT Cottage-Hot Tub, Billiards, Golf Cart, Pet Friendly
Vineyard View | Walk to Wineries & River| Hot Tub
Terrace/patio

Vineyard View | Walk to Wineries & River| Hot Tub

10.0 out of 10, Exceptional, (57)
"Perfect house for the four of us and our dog. Great location and we will be back!"
The price is SAR 1,117
SAR 1,758 total
includes taxes & fees
27 Mar - 28 Mar
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)
"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!
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

9.2 out of 10, Wonderful, (17)
"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.
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

3.5 star property
8.6 out of 10, Excellent, (83)
"No frills awesome place "
The Abbey Apartments By Barsala
2125 Superior Living
Interior

2125 Superior Living

2.0 star property
5.6 out of 10, (20)
"I would like to start by expressing my appreciation for the prompt responses I received every time I had a question or concern regarding my reservation. However, I would like to address a few issues we encountered during our stay. Your amenities list states that we would be provided with shampoo and towels. Unfortunately, we did not receive any shampoo, and although we had towels, there were only two provided for three adults. Additionally, the washcloths appeared to be dirty. When we prepared...
The price is SAR 251
SAR 670 total
includes taxes & fees
30 Mar - 31 Mar
2125 Superior Living
Barsala At The Monroe Apartments
Interior

Barsala At The Monroe Apartments

4.0 star property
9.0 out of 10, Wonderful, (21)
"Nice place and great host"
Barsala At The Monroe Apartments
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?
Booking a cottage in Chesterland is as simple as entering your travel dates and choosing an ideal place for outdoor recreation and relaxation. From ritzy retreats to affordable stays and cottages that feature conveniences like a kitchen, Expedia has something for all tastes. As for unbeatable deals? We’ve got them as well!
How can I find cheap cottages in Chesterland?
The easiest way to compare cheap cottages in Chesterland is with Expedia’s handy filter tool. Narrow your search by star rating, amenities and budget to snag unbeatable prices with only a few clicks.