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Compare 499 Vacation Homes in Chesterland with updated reviews, rates, and availability.

Large duplex king size bed and two queen size

9.2 out of 10, Wonderful, (51)
"This property was of adequate size for our family."
The price is AED 536
AED 823 total
includes taxes & fees
1 Jun - 2 Jun
Large duplex king size bed and two queen size

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

9.6 out of 10, Exceptional, (56)
"Check in/check out process was seamless and very easy! Host was incredibly nice and helpful with everything we needed. The property was extremely cozy and was very easy to settle in to. Very clean and comfy, already looking forward to another stay!!"
The price is AED 323
AED 649 total
includes taxes & fees
3 Jun - 4 Jun
Lovely in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Luxury Downtown Townhome w/ Private Garage Unit 13

9.6 out of 10, Exceptional, (53)
"Great place to stay!"
The price is AED 239
AED 701 total
includes taxes & fees
2 Jun - 3 Jun
Luxury Downtown Townhome w/ Private Garage Unit 13

City living W/Hot tub, Pool Table, Movie Theater!

10.0 out of 10, Exceptional, (29)
"This place was amazing and the host was just as amazing!"
City living W/Hot tub, Pool Table, Movie Theater!

Luxury Downtown Townhome w/ Private Garage Unit 14

9.8 out of 10, Exceptional, (22)
"Very nice place to stay. "
The price is AED 239
AED 701 total
includes taxes & fees
2 Jun - 3 Jun
Luxury Downtown Townhome w/ Private Garage Unit 14

Ohio City Getaway W/ Hot Tub, Pool Table and more!

9.6 out of 10, Exceptional, (56)
"This property is all that is advertised very clean and spacious really enjoyed our stay "
Ohio City Getaway W/ Hot Tub, Pool Table and more!

Crisp 2 bedroom upstairs apartment in historic duplex

10.0 out of 10, Exceptional, (33)
"Great location, great host, very private, safe neighborhood, easy parking and access to everything. I would definitely stay again!"
Crisp 2 bedroom upstairs apartment in historic duplex

Hot Tremont House - 6 Bed 3 Bath

9.8 out of 10, Exceptional, (6)
"The house was clean and vibrant! Great atmosphere!"
The price is AED 1,035
AED 2,641 total
includes taxes & fees
9 Jun - 10 Jun
Hot Tremont House - 6 Bed 3 Bath

Mid Century Guest House on Wooded Lot

10.0 out of 10, Exceptional, (44)
"We really like it was very clean and people was very friendly "
Mid Century Guest House on Wooded Lot

Hot Tub|Ping Pong|Sleeps 9|Retro Fun

10.0 out of 10, Exceptional, (5)
The price is AED 787
AED 1,919 total
includes taxes & fees
2 Jun - 3 Jun
Hot Tub|Ping Pong|Sleeps 9|Retro Fun

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

9.8 out of 10, Exceptional, (43)
"Stayed for an audition at Cleveland institute of music and Case western. Very close and great restaurants and parks nearby."
The price is AED 437
AED 775 total
includes taxes & fees
16 Jun - 17 Jun
Charm in Larchmere! near Cleveland Clinic, CWRU, Univ Hosp, Downtown, w/Porch!

Lakefront Escape With Hot Tub & Modern Comforts

10.0 out of 10, Exceptional, (3)
"We enjoyed our time staying at this house! "
The price is AED 734
AED 1,533 total
includes taxes & fees
2 Jun - 3 Jun
Lakefront Escape With Hot Tub & Modern Comforts

Lovely 2 Bedroom Unit with a Hot Tub

9.6 out of 10, Exceptional, (55)
"Adorable home. Nice and comfortable. Had some trouble finding the parking area but eventually figured it out"
The price is AED 511
AED 750 total
includes taxes & fees
2 Jun - 3 Jun
Lovely 2 Bedroom Unit with a Hot Tub

Luxury Downtown Townhome w/ Private Garage Unit 16

2.0 star property
9.4 out of 10, Exceptional, (9)
"Fantastic stay! Easy check in process. "
The price is AED 239
AED 701 total
includes taxes & fees
1 Jun - 2 Jun
Luxury Downtown Townhome w/ Private Garage Unit 16

Lakefront Oasis Retreat Private Beach-Hot Tub-Pet Friendly-3 Bd/2 B-King Suite

10.0 out of 10, Exceptional, (27)
"Great home with a beautiful view. Owner was quick to answer questions and the house was convenient to restaurants and parks."
The price is AED 1,524
AED 2,450 total
includes taxes & fees
9 Jun - 10 Jun
Lakefront Oasis Retreat Private Beach-Hot Tub-Pet Friendly-3 Bd/2 B-King Suite

Luxury Downtown Townhome w/ Private Garage Unit 5

9.4 out of 10, Exceptional, (16)
"This place was perfect for us."
The price is AED 239
AED 701 total
includes taxes & fees
1 Jun - 2 Jun
Luxury Downtown Townhome w/ Private Garage Unit 5

Modern large home near Cleveland

10.0 out of 10, Exceptional, (62)
"Great accommodations, access to downtown, Flats, food Great time with life long Friends."
Modern large home near Cleveland

PrivateDECKs+ ArcadeRetro + GameRm + 3Min to Downtown II VibeonViny

10.0 out of 10, Exceptional, (1)
"Property and location are amazing. Jo was very helpful and accommodating. "
The price is AED 531
AED 1,340 total
includes taxes & fees
2 Jun - 3 Jun
PrivateDECKs+ ArcadeRetro + GameRm + 3Min to Downtown II VibeonViny

Little Italy! Close to Cleveland Clinic, University Hospital & University Circle

10.0 out of 10, Exceptional, (28)
"A very comfortable, high quality, and well equipped unit. Location is fabulous and the owner manages very professionally with a lot of attention to details. We would definitely stay here again. "
The price is AED 533
AED 1,078 total
includes taxes & fees
1 Jun - 2 Jun
Little Italy! Close to Cleveland Clinic, University Hospital & University Circle

Cozy & Quiet beautiful 4 bedrooms , close to downtown, Cleve clinic

10.0 out of 10, Exceptional, (8)
"Perfect weekend stay. Would book again"
Cozy & Quiet beautiful 4 bedrooms , close to downtown, Cleve clinic
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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