Photo by Kristin DePlatchett

Chesterland Holiday Rentals

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Holiday Rentals in Chesterland

The Abbey Apartments By Barsala

4.0 star property
8.4 out of 10, Very good, (72)
"Great place! Quiet and clean and close to everything you want to do downtown. Loved it!"
The Abbey Apartments By Barsala

CLE BNB Getaway ★ 15 Guests ★ Stunning Kitchen ★ Game Room ★ Big Fenced Yard

8.8 out of 10, Excellent, (68)
"The home was perfect for our large family. Host was very helpful. Would absolutely stay at this home again ."
CLE BNB Getaway ★ 15 Guests ★ Stunning Kitchen ★ Game Room ★ Big Fenced Yard

Liquid Living On The Lake

9.0 out of 10, Wonderful, (41)
"Great clean quiet property! Great prices too! "
The price is AU$295
includes taxes & fees
2 Dec - 3 Dec
Liquid Living On The Lake

Medley Condos By Barsala

3.5 star property
7.6 out of 10, Good, (28)
"We enjoyed this property enough to book it again in May. It’s a quick 5min walk to the cleveland clinic cancer center, The reason for our stay. The grocery store downstairs was the best part. We were able to make our meals at the condo. We ubered to little italy and the baseball field for less then $15. Friendly staff and they even had an eclipse party on the outdoor area with music, pizza and soda. My only complaints was our dishwasher didn’t work any the water had a sulfer smell the first...
Medley Condos By Barsala

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

9.6 out of 10, Exceptional, (47)
"Great house! "
Ohio City Getaway W/ Hot Tub, Pool Table and more!

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

10.0 out of 10, Exceptional, (37)
"Beautiful home great restaurants and nice accommodations very close to beach "
The price is AU$653
includes taxes & fees
30 Nov - 1 Dec
RIVERFRONT Cottage-Hot Tub, Billiards, Golf Cart, Pet Friendly

Mid Century Guest House on Wooded Lot

10.0 out of 10, Exceptional, (41)
"Very nice and cozy. Quiet and served all our needs. We would definitely return if in the area. "
Mid Century Guest House on Wooded Lot

Large Remodeled 4 Bedroom! Only 7 Minutes to Downtown!

9.6 out of 10, Exceptional, (16)
"Great property and perfect location. "
Large Remodeled 4 Bedroom! Only 7 Minutes to Downtown!

Cozy CLE East- MINUTES from Clinic, UH, Case, Downtown, Edgewater

9.8 out of 10, Exceptional, (10)
"Room is cozy and perfect for two people. The parking lot is great. Within a half hour of everything.. went to west side market, the Christmas story house, art museum and walked to little Italy for dinner. Kia was very thorough with her instructions and very prompt with her response "
The price is AU$249
includes taxes & fees
27 Nov - 28 Nov
Cozy CLE East- MINUTES from Clinic, UH, Case, Downtown, Edgewater

Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!

10.0 out of 10, Exceptional, (40)
"We loved our stay! We enjoyed walking to a local coffee shop! We loved the house so much that we opted to get food and stay in to enjoy the place! Will be back. "
The price is AU$336
includes taxes & fees
2 Dec - 3 Dec
Updated Cleveland Apt: Heart of Little Italy! with Massage Chair & Hot Tub!

Downtown Cleveland Loft - Lake Views w/Private Rooftop!

9.8 out of 10, Exceptional, (73)
"We enjoyed our stay. It had a great location and the accommodations we’re comfortable, clean, and inviting. I would recommend! "
Downtown Cleveland Loft - Lake Views w/Private Rooftop!

Crown royal presidential suite and fitness center

9.0 out of 10, Wonderful, (33)
"My husband and I both agreed that the room was exactly as described. It really was perfect for just the two of us. The bed is SO comfy! We booked it because it has a fitness room included. The neighborhood is quiet, and we were central all the places that we needed to get to for the week. The host was responsive to our messages, and we appreciated some of the details, like the bottles of water in the mini fridge. Would recommend!"
The price is AU$202
includes taxes & fees
27 Nov - 28 Nov
Crown royal presidential suite and fitness center

Forever spring cabin

10.0 out of 10, Exceptional, (206)
"We thoroughly enjoyed staying at this pristinely kept cottage. Everything was perfect! From the front porch, to the whirlpool tub and an added bonus were the 2 cutest little pooches to meet and greet us and visited us each day and even joined me on my nature hike. Nice firepit a."
Forever spring cabin

LOCATION!- City Getaway in the FLATS!

9.6 out of 10, Exceptional, (23)
"Cool place with a lot of things to do. Good communication with the owner. "
LOCATION!- City Getaway in the FLATS!

Cozy Downtown Modern Condo in the Heart of it all

9.6 out of 10, Exceptional, (113)
"The location was perfect for walking around downtown Cleveland. "
The price is AU$209
includes taxes & fees
2 Dec - 3 Dec
Cozy Downtown Modern Condo in the Heart of it all

Cal King bed, free parking, by Downtown & Clinic

9.2 out of 10, Wonderful, (24)
"Nice place. Great communication "
The price is AU$192
includes taxes & fees
27 Nov - 28 Nov
Cal King bed, free parking, by Downtown & Clinic

"Gull Cottage" - Lake Erie waterfront - Expansive Views, Historic Cottage Charm

10.0 out of 10, Exceptional, (54)
"We really loved this house! Beautiful view of the lake, quiet neighborhood, good access to nearby shopping. The house is in great shape, extremely well maintained. If you like clean, this is for you! We don't rent often so this was a wonderful experience. The host was incredibly helpful and always available. Next time in Cleveland area, we will be sure to book this again!"
The price is AU$1,002
includes taxes & fees
1 Dec - 2 Dec
"Gull Cottage" - Lake Erie waterfront - Expansive Views, Historic Cottage Charm

Lovely 2 Bedroom Unit with a Hot Tub

9.6 out of 10, Exceptional, (45)
"Property was well kept and area was safe and walkable. "
The price is AU$298
includes taxes & fees
3 Dec - 4 Dec
Lovely 2 Bedroom Unit with a Hot Tub

Contemporary Coventry:1 bd w Fireplace. NEAR Case, Cle Clinic, UH, downtown!

9.0 out of 10, Wonderful, (28)
"It was awesome place. A bit old but was fine for the money. "
The price is AU$257
includes taxes & fees
1 Dec - 2 Dec
Contemporary Coventry:1 bd w Fireplace. NEAR Case, Cle Clinic, UH, downtown!

Emerald Oasis: Stylish Tremont 2BR Lower Unit by Christmas Story House | Parking • 7 Min to Downtown

9.2 out of 10, Wonderful, (13)
"We enjoyed the neighborhood we stayed in. It was close to the Christmas Story .resbaRowleys... it was a great time."
The price is AU$274
includes taxes & fees
1 Dec - 2 Dec
Emerald Oasis: Stylish Tremont 2BR Lower Unit by Christmas Story House | Parking • 7 Min to Downtown
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 types of properties in Chesterland you may be interested in

Drury Plaza Hotel Cleveland Downtown

3.0 star property
9.4 out of 10, Exceptional, (2353)
"I would recommend you bring your own pillow."
The price is AU$217
includes taxes & fees
1 Dec - 2 Dec
Drury Plaza Hotel Cleveland Downtown

The Westin Cleveland Downtown

4.0 star property
8.4 out of 10, Very good, (1018)
"The body wash was empty "
The price is AU$197
includes taxes & fees
27 Nov - 28 Nov
The Westin Cleveland Downtown

Extended Stay America Premier Suites - Cleveland - Independence

2.5 star property
7.6 out of 10, Good, (1352)
"Much nicer than I expected for the price. I would definitely stay there again. One thing to notice however that even though they have a small kitchen there are no plates or utensils or dishes of any kind so bring your own."
The price is AU$127
includes taxes & fees
24 Dec - 25 Dec
Extended Stay America Premier Suites - Cleveland - Independence
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there holiday rentals in Chesterland?

Yes, there are holiday rentals close to the most popular sights in Chesterland, or you can select a more secluded option if you're looking for a relaxing stay. Chesterland is known for its golf courses and ski areas.

What are some of the best holiday rentals that Chesterland has to offer?

Ohio City Getaway! Sleeps 12, Games, Near Downtown: This holiday home rental outside of Chesterland has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Chesterland?

While exploring the area, visit family-friendly sights like Pioneer Waterland & Dry Fun Park, or get outside and enjoy nature at Chagrin River. Fowler's Mill Golf Course and Alpine Valley are other places to visit while you're in town.

What are holiday rentals like in Chesterland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterland. Holiday rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a small group gathering.