Chesterland Vacation Rentals

  • 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

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Chesterland vacation rentals

A grassy area with two Adirondack chairs and a fire pit, overlooking a body of water.

1. Coastal Lake Erie Cottage w/ Amazing Water Views!

Coastal Lake Erie Cottage w/ Amazing Water Views!
3.0 star property
Euclid
10.0 out of 10, Exceptional, (2 reviews)
"loved the water view but not so fond of the apartment building next door"
United States
gregory
The price is AEDĀ 389
AEDĀ 893 total
includes taxes & fees
10 Nov - 11 Nov
Coastal Lake Erie Cottage w/ Amazing Water Views!
Living area

2. Sleek DT Cleveland Apt at City Club

Sleek DT Cleveland Apt at City Club
3.0 star property
Downtown Cleveland
9.2 out of 10, Wonderful, (263 reviews)
"Enjoyed our stay, right downtown and accessible to everything."
United States
Sean
The price is AEDĀ 231
AEDĀ 905 total
includes taxes & fees
9 Nov - 10 Nov
Sleek DT Cleveland Apt at City Club
A modern kitchen with stainless steel appliances, wooden cabinets, a large island with a sink, and a view through a window.

3. ROVE LIVING/KB - Baricelli

ROVE LIVING/KB - Baricelli
4.0 star property
University Circle
8.0 out of 10, Very good, (3 reviews)
"The check-in is a bit tedious but necessary. The unit was spotless and well appointed. it is very convenient to Case Western Reserve University, University Hospitals, and Little Italy. There is a great dive bar across the street and the Murray Hill Market is a few blocks down Murray Hill Rd. Needless to say there are a lot Italian Restaurants within a short walk. One other thing, it is a very quiet neighborhood, which I was not expecting."
United States
Pete
The price is AEDĀ 279
AEDĀ 716 total
includes taxes & fees
11 Nov - 12 Nov
ROVE LIVING/KB - Baricelli
A compact kitchen with modern appliances, a dining area with a table and chairs, and a sofa in a hallway.

4. Hilliard Lofts

Hilliard Lofts
2.0 star property
Downtown Cleveland
8.6 out of 10, Excellent, (4 reviews)
"Clean, comfortable loft apartment, walking distance to downtown, easy check in/check out."
United States
Craig
The price is AEDĀ 496
AEDĀ 906 total
includes taxes & fees
8 Nov - 9 Nov
Hilliard Lofts
A bedroom with a bed, a dresser, a nightstand, a lamp, a window, and a ceiling fan.

5. 6 Mi to Dtwn! Historic Haven in Cleveland

6 Mi to Dtwn! Historic Haven in Cleveland
3.5 star property
Brooklyn Centre
The price is AEDĀ 823
AEDĀ 1,688 total
includes taxes & fees
8 Nov - 9 Nov
6 Mi to Dtwn! Historic Haven in Cleveland
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

Find vacation rentals that suit your style

Apartment image
Apartments
Apartments
apart-hotel image
Aparthotels
Aparthotels

Top Chesterland Hotel Reviews

A modern lounge area with a curved sofa, multiple chairs, a wooden table, and large windows offering a view of the parking lot and cityscape.
Holiday Inn Cleveland-Mayfield by IHG

Holiday Inn Cleveland-Mayfield by IHG

Holiday Inn Cleveland-Mayfield by IHG
Mayfield

10/10 Excellent

Facilities are really nice after their recent renovation. Their location is most convenient and the restaurant downstairs has amazing Italian food. I would stay again!
United States
SIMON
Reviewed June 4, 2023
Holiday Inn Cleveland-Mayfield by IHG

Frequently Asked Questions

Are there vacation rentals in Chesterland?

Yes, you can find vacation rentals close to popular sights in Chesterland, or you can choose a more secluded option if you're looking for relaxation. Chesterland is known for its golf courses and ski areas.

What's the top vacation rental that Chesterland has to offer?

Charm near Cleve Clinic/CWRU/UH - Larchmere Blvd w/Porch: This vacation home rental near Chesterland offers a balcony, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games.

What can I see and do in Chesterland?

Chagrin River and Chesterland City Park are a couple of lovely local spots to get outside and enjoy nature. Alpine Valley and Berkshire Hill Golf Course are other places to visit while you're in town.

What are vacation rentals like in Chesterland?

Vacation rentals are private properties you can book for several days or longer in Chesterland. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for family gatherings.