599+ Private Villas and Holiday Rentals in Chesterland |
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Chesterland Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Chesterland

Discover more than 599 vacation rentals available in Chesterland. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Chesterland.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Chesterland, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Chesterland. On average, places to stay near Chesterland offer 847.6 ft², with nightly prices averaging ZA R3,980.

With Casai, finding and comparing holiday rentals in Chesterland is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Chesterland

Type Count
Vacation Homes 373
Holiday Apartments 101
Cottages 12
Villas 5

Use these Quick Filters to Find a Holiday Rental in Chesterland

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Chesterland.

Weather in Chesterland, OH

View the weather forecast for Chesterland before booking your Chesterland Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Chesterland, OH

Casai offers a large selection of top attractions around Chesterland . Research things to do on your vacation before you visit Chesterland.


Alpine Valley
Fowler's Mill Golf Course
Rock and Roll Hall of Fame
Cleveland Clinic
Rocket Mortgage FieldHouse
Progressive Field
FirstEnergy Stadium
Case Western Reserve University
JACK Cleveland Casino
University Hospitals of Cleveland
Cleveland Convention Center
Cleveland Museum of Art
MGM Northfield Park
Cleveland State University
Cuyahoga Valley National Park
Greater Cleveland Aquarium
Wolstein Center
West Side Market
Great Lakes Science Center
Cleveland Metroparks Zoo

Other Places to Stay in Chesterland, OH


Fowler's Mill Golf Course 267 Properties
Alpine Valley 199 Properties

Frequently Asked Questions About Chesterland?

What are the top holiday rentals in Chesterland?

With numerous options available in Chesterland, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Chesterland:

How many holiday rentals have private pools in Chesterland?

Discover a selection of holiday rentals with private pools near Chesterland with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Chesterland are best for families?

If you're searching for a family-friendly holiday home in Chesterland, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Chesterland:

How many Casai.co.za holiday rentals are available in Chesterland?

As of 2025, Casai boasts over 599 properties listed in the Chesterland area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Chesterland.


People Also Ask

There are 599 Chesterland, OH Holiday Rentals

Recently Booked Holiday Rentals in Chesterland