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Our top choices for Chesterland vacation homes

Crisp 2 bedroom upstairs apartment in historic duplex

Crisp 2 bedroom upstairs apartment in historic duplex
Stockyards
10.0 out of 10, Exceptional, (46)
"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 AED 360
AED 554 total
includes taxes & fees
11 Dec - 12 Dec
Crisp 2 bedroom upstairs apartment in historic duplex

Victorian Studio Steps from Cleveland Clinic

Victorian Studio Steps from Cleveland Clinic
Hough
10.0 out of 10, Exceptional, (1)
The price is AED 329
AED 807 total
includes taxes & fees
11 Dec - 12 Dec
Victorian Studio Steps from Cleveland Clinic

Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!
Buckeye-Shaker
9.8 out of 10, Exceptional, (58)
"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 AED 264
AED 585 total
includes taxes & fees
11 Dec - 12 Dec
Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (94)
"My stay here was wonderful! James and Anna were very welcoming and such a clean place when arriving! I love this area as I grew up here and was close to many destinations I had planned. I will definitely be returning again."
United States
Sarah S.
The price is AED 569
AED 830 total
includes taxes & fees
13 Dec - 14 Dec
Little house on the farm

Luxury Downtown Townhome w/ Private Garage Unit 16

Luxury Downtown Townhome w/ Private Garage Unit 16
2.0 star property
Downtown Cleveland
9.0 out of 10, Wonderful, (24)
"Location was great for a quick family weekend trip. "
United States
Crystal P.
The price is AED 184
AED 634 total
includes taxes & fees
22 Dec - 23 Dec
Luxury Downtown Townhome w/ Private Garage Unit 16

Shaker Square|Sleeps 4|Front Porch|Coffee Station

Shaker Square|Sleeps 4|Front Porch|Coffee Station
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 AED 299
AED 1,109 total
includes taxes & fees
11 Dec - 12 Dec
Shaker Square|Sleeps 4|Front Porch|Coffee Station

Charming 3-Bedroom Pet-Friendly Home by Lake Erie

Charming 3-Bedroom Pet-Friendly Home by Lake Erie
Euclid
10.0 out of 10, Exceptional, (3)
"Pet friendly"
United States
Gac R.
The price is AED 367
AED 826 total
includes taxes & fees
8 Jan - 9 January 2026
Charming 3-Bedroom Pet-Friendly Home by Lake Erie

Luxury Downtown Townhome w/ Private Garage Unit 14

Luxury Downtown Townhome w/ Private Garage Unit 14
Downtown Cleveland
9.6 out of 10, Exceptional, (37)
"Very nice, clean easy to book and communication was great with owner! "
United States
Craig & Amy K.
The price is AED 184
AED 634 total
includes taxes & fees
14 Dec - 15 Dec
Luxury Downtown Townhome w/ Private Garage Unit 14

Home Away from Home The Garfield Grove a Nature & Nostalgia Retreat

Home Away from Home The Garfield Grove a Nature & Nostalgia Retreat
Garfield Heights
10.0 out of 10, Exceptional, (3)
"This was a lovely home to stay at with our 4 kids and 3 dogs. "
United States
Kelli C.
The price is AED 500
AED 1,389 total
includes taxes & fees
11 Dec - 12 Dec
Home Away from Home The Garfield Grove a Nature & Nostalgia Retreat

Acadia Farms Carriage House

Acadia Farms Carriage House
Northfield
10.0 out of 10, Exceptional, (1)
"The Carriage House was very clean, and has everything you need in a small floorplan. And the location was perfect for our plans. We came up to hike the Cuyahoga Valley park, and to go to the Rock & Roll hall of fame. "
United States
Jeff S.
The price is AED 424
AED 733 total
includes taxes & fees
11 Dec - 12 Dec
Acadia Farms Carriage House

Christmas Avail • Hulu • 15 mi to DT CLE • King • Soaking Tub • Fast WiFi

Christmas Avail • Hulu • 15 mi to DT CLE • King • Soaking Tub • Fast WiFi
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

Spacious Ohio City Oasis | Close to Breweries+WSM

Spacious Ohio City Oasis | Close to Breweries+WSM
Ohio City
10.0 out of 10, Exceptional, (27)
"We stayed here to be close to Cleveland Clinic. Very easy to get to, plenty of room for our family. "
United States
Tracy C.
The price is AED 309
AED 727 total
includes taxes & fees
14 Dec - 15 Dec
Spacious Ohio City Oasis | Close to Breweries+WSM

Large duplex king size bed and two queen size

Large duplex king size bed and two queen size
Cleveland Heights
9.2 out of 10, Wonderful, (67)
"The house was very nice"
United States
William
The price is AED 367
AED 618 total
includes taxes & fees
5 Jan - 6 January 2026
Large duplex king size bed and two queen size

The House Hotels - Superior Road

The House Hotels - Superior Road
Cleveland Heights
9.4 out of 10, Exceptional, (15)
"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 AED 405
AED 809 total
includes taxes & fees
11 Dec - 12 Dec
The House Hotels - Superior Road

Charming Spacious & Affordable. Gem of Parma! Modern space superbly clean.

Charming Spacious & Affordable. Gem of Parma! Modern space superbly clean.
2.0 star property
Parma
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 AED 433
AED 839 total
includes taxes & fees
15 Dec - 16 Dec
Charming Spacious & Affordable. Gem of Parma! Modern space superbly clean.

Urban Art Escape in Gordon Sq. W/King Size Bed

Urban Art Escape in Gordon Sq. W/King Size Bed
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 AED 316
AED 805 total
includes taxes & fees
11 Dec - 12 Dec
Urban Art Escape in Gordon Sq. W/King Size Bed

Soak and Play: Hot Tub + Family Arcade Fun

Soak and Play: Hot Tub + Family Arcade Fun
Euclid
10.0 out of 10, Exceptional, (3)
"Good accommodations and clear communication with the host. "
United States
Jared D.
The price is AED 481
AED 1,091 total
includes taxes & fees
15 Dec - 16 Dec
Soak and Play: Hot Tub + Family Arcade Fun

Historic Cleveland Gem | Jacuzzi Tub & Fire Pit

Historic Cleveland Gem | Jacuzzi Tub & Fire Pit
Ohio City
9.4 out of 10, Exceptional, (18)
"We had a nice stay and would book again when staying in the area. Hosts made check-in and check out easy, and were super responsive. Location is good for walking to bars and restaurants."
United States
John B.
The price is AED 434
AED 1,163 total
includes taxes & fees
11 Dec - 12 Dec
Historic Cleveland Gem | Jacuzzi Tub & Fire Pit

Small town vibes in Garrettsville

Small town vibes in Garrettsville
Garrettsville
10.0 out of 10, Exceptional, (3)
"Very clean, solid rental. "
United States
Christopher P.
The price is AED 950
AED 1,435 total
includes taxes & fees
11 Dec - 12 Dec
Small town vibes in Garrettsville

Lux Ohio City Gem

Lux Ohio City Gem
Ohio City
9.4 out of 10, Exceptional, (3)
"Lovely place in a great neighborhood. Walkable to tons of restaurants and close to all of the downtown attractions. Everything about our stay here was perfect. "
United States
Andrew R.
The price is AED 357
AED 1,112 total
includes taxes & fees
11 Dec - 12 Dec
Lux Ohio City Gem
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 Chesterland Hotel Reviews