Photo by Kristin DePlatchett

Search Vacation Homes in Chesterland

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec
In one month
26 Dec - 28 Dec
In two months
23 Jan - 25 Jan

Vacation Homes in Chesterland

Outdoor dining
Crisp 2 bedroom upstairs apartment in historic duplex

Vacation Home in Stockyards

10.0 out of 10, Exceptional, (45)
"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 SAR 368
SAR 566 total
includes taxes & fees
1 Dec - 2 Dec
Crisp 2 bedroom upstairs apartment in historic duplex
Fridge, microwave, oven, stovetop
Victorian Studio Steps from Cleveland Clinic

Vacation Home in Hough

10.0 out of 10, Exceptional, (1)
The price is SAR 336
SAR 824 total
includes taxes & fees
1 Dec - 2 Dec
Victorian Studio Steps from Cleveland Clinic
Exterior detail
Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Vacation Home in Buckeye-Shaker

9.8 out of 10, Exceptional, (56)
"We had made a prior request that housekeeping avoid scented cleaning products as much as possible (due to allergies and sensitivities of people in our group). We were very pleased with their efforts, and our stay was allergy-free! Also, the host, Ken Love, was very responsive when I had questions/comments during and after our stay."
United States
Patricia
The price is SAR 270
SAR 597 total
includes taxes & fees
1 Dec - 2 Dec
Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!
Exterior
Charming 3-Bedroom Pet-Friendly Home by Lake Erie

Vacation Home in Euclid

10.0 out of 10, Exceptional, (3)
"Pet friendly"
United States
Gac R.
The price is SAR 216
SAR 666 total
includes taxes & fees
1 Dec - 2 Dec
Charming 3-Bedroom Pet-Friendly Home by Lake Erie
Fridge, microwave, oven, stovetop
Luxury Downtown Townhome w/ Private Garage Unit 16

Vacation Home in Downtown Cleveland

2.0 star property
9.2 out of 10, Wonderful, (21)
"Location was great for a quick family weekend trip. "
United States
Crystal P.
The price is SAR 150
SAR 607 total
includes taxes & fees
1 Dec - 2 Dec
Luxury Downtown Townhome w/ Private Garage Unit 16
Fridge, microwave, oven, stovetop
Luxury Downtown Townhome w/ Private Garage Unit 14

Vacation Home in Downtown Cleveland

9.6 out of 10, Exceptional, (37)
"Good location, walkable to sports. "
United States
Michael C.
The price is SAR 206
SAR 668 total
includes taxes & fees
8 Dec - 9 Dec
Luxury Downtown Townhome w/ Private Garage Unit 14
Exterior detail
Little house on the farm

Vacation Home in Middlefield

10.0 out of 10, Exceptional, (94)
"We stay at this sweet little house for our bi-annual family reunion and just love the beautiful, quiet, country setting. The house is neat and clean with everything we need to feel right at home. "
United States
Clarissa M.
The price is SAR 582
SAR 848 total
includes taxes & fees
8 Dec - 9 Dec
Little house on the farm
Fridge, microwave, oven, stovetop
Stylish Ohio City Retreat - Walk to West Side Market and Breweries

Vacation Home in Ohio City

9.8 out of 10, Exceptional, (19)
"I had no complaints about our stay whatsoever. It was a very nice place."
United States
nick f.
The price is SAR 278
SAR 623 total
includes taxes & fees
1 Dec - 2 Dec
Stylish Ohio City Retreat - Walk to West Side Market and Breweries
Outdoor dining
Christmas Avail • Hulu • 15 mi to DT CLE • King • Soaking Tub • Fast WiFi

Vacation Home in Euclid

10.0 out of 10, Exceptional, (2)
"Lovely house. Decorated beautifully and all the extras Val put in it was awesome. Highly recommend staying there."
United States
Deb L.
Christmas Avail • Hulu • 15 mi to DT CLE • King • Soaking Tub • Fast WiFi
Fridge, microwave, oven, stovetop
Luxury Downtown Townhome w/ Private Garage Unit 5

Vacation Home in Downtown Cleveland

9.0 out of 10, Wonderful, (27)
"Had a great time very convenient, extremely clean and communication!"
United States
Wadsworth J.
The price is SAR 131
SAR 586 total
includes taxes & fees
1 Dec - 2 Dec
Luxury Downtown Townhome w/ Private Garage Unit 5
Terrace/patio
Urban Art Escape in Gordon Sq. W/King Size Bed

Vacation Home in Detroit - Shoreway

9.0 out of 10, Wonderful, (2)
"The location was great especially because parking was kind of scarce we could walk up the street and everything we could want was right there. The home was clean and practical. We will definitely book when we come to Cleveland "
United States
Cierra H.
The price is SAR 323
SAR 830 total
includes taxes & fees
1 Dec - 2 Dec
Urban Art Escape in Gordon Sq. W/King Size Bed
Dining
Shaker Square|Sleeps 4|Front Porch|Coffee Station

Vacation Home in Buckeye-Shaker

10.0 out of 10, Exceptional, (4)
"It is a clean, well maintained property. It was very comfortable & it is in a nice neighborhood."
United States
Julie S.
The price is SAR 359
SAR 1,198 total
includes taxes & fees
4 Dec - 5 Dec
Shaker Square|Sleeps 4|Front Porch|Coffee Station
Property grounds
Fun 3 BR Home in Ohio City | Game Room | Sleeps 11

Vacation Home in Ohio City

10.0 out of 10, Exceptional, (3)
"Great communication with host. He checked in with me to make sure everything was to our liking and that we got settled in ok. It was perfect for our night of sitting around the table and playing games/cards with friends. We also had a blast playing Galaga and Ms. Pac-Man. Close to the Westside Market area which was convenient. Will definitely stay again when in the area. "
United States
Jaime S.
The price is SAR 300
SAR 1,062 total
includes taxes & fees
2 Dec - 3 Dec
Fun 3 BR Home in Ohio City | Game Room | Sleeps 11
Interior
Historic Loft in the Heart of Downtown • Gym

Vacation Home in Downtown Cleveland

2.0 star property
8.0 out of 10, Very Good, (1)
"There was no key for the property for the duration of the stay. And though security was helpful, it really wasn’t a comfortable situation."
United States
Conor C.
The price is SAR 198
SAR 656 total
includes taxes & fees
1 Dec - 2 Dec
Historic Loft in the Heart of Downtown • Gym
Property grounds
The House Hotels - Superior Road

Vacation Home in Cleveland Heights

9.4 out of 10, Exceptional, (14)
"This lovely small home was perfect for attending our son’s graduation from CWRU. The beds were very comfortable with nice linens and lots of high end pillows. Towels were soft and fresh smelling. The sitting and dining areas had comfortable furniture in good shape. The kitchen was a little dated but had everything we needed to make breakfast ( that’s all we cooked). The street was very quiet for sleeping"
United States
Valerie S.
The price is SAR 414
SAR 834 total
includes taxes & fees
1 Dec - 2 Dec
The House Hotels - Superior Road
Interior
Quiet and comfortable

Vacation Home in Central

2.0 star property
10.0 out of 10, Exceptional, (1)
"We enjoyed our stay at the home. The owner was very responsive and the home was near several good locations within a few miles. We loved having separate bathrooms for each couple. Our only suggestion would be to add small televisions in the bedrooms and a new grill. "
United States
Angela L.
The price is SAR 672
SAR 1,107 total
includes taxes & fees
31 Dec - 1 January 2026
Quiet and comfortable
Smart TV, table tennis, books
Spring Special In The HEART of Cleveland - Limited Time Offer

Vacation Home in Cleveland Heights

9.6 out of 10, Exceptional, (13)
"My family is from Cleveland and we returned for a family gathering. The location was perfect for us and it slept all 10 of us comfortably with extra room to spare. "
United States
yasmeen h.
The price is SAR 369
SAR 1,160 total
includes taxes & fees
1 Dec - 2 Dec
Spring Special In The HEART of Cleveland - Limited Time Offer
Fridge, microwave, oven, stovetop
Soak and Play: Hot Tub + Family Arcade Fun

Vacation Home in Euclid

10.0 out of 10, Exceptional, (3)
"Good accommodations and clear communication with the host. "
United States
Jared D.
The price is SAR 371
SAR 969 total
includes taxes & fees
2 Dec - 3 Dec
Soak and Play: Hot Tub + Family Arcade Fun
Outdoor dining
Charming Spacious & Affordable. Gem of Parma! Modern space superbly clean.

Vacation Home in Parma

2.0 star property
10.0 out of 10, Exceptional, (11)
"Wonderful hosts, answered all my questions promptly and had great recommendations! Home was super clean and had everything we needed and then some! "
United States
Donna B.
The price is SAR 483
SAR 908 total
includes taxes & fees
1 Dec - 2 Dec
Charming Spacious & Affordable. Gem of Parma! Modern space superbly clean.
4 bedrooms, desk, free WiFi, bed sheets
Escape to Fun: Hot Tub & Game Arcade Retreat

Vacation Home in Euclid

9.0 out of 10, Wonderful, (12)
"Lovely stay and our host Michelle was very helpful and welcoming. We would be happy to stay here again. "
United States
Sheree Y.
The price is SAR 458
SAR 1,069 total
includes taxes & fees
1 Dec - 2 Dec
Escape to Fun: Hot Tub & Game Arcade Retreat
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.
View all properties

White Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterland Hotel Reviews

The Glidden House

The Glidden House

10/10 Excellent
"Friendly staff, great breakfast!"
Roger 1-night trip
Posted 2 days ago
The Glidden House