Discover Your Perfect Chesapeake Vacation Homes

Chesapeake Luxury Rentals

See More Chesapeake Luxury Vacation Rentals
Find More Chesapeake Villas, Resorts, & Rentals on BedroomVillas

Chesapeake Pet Friendly Vacation Rentals

See More Pet-Friendly Vacation Rentals in Chesapeake on PetFriendly.io

Why Choose Rent By Owner for your Chesapeake Vacation Rental Homes?

What makes our Vacation Rentals special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Chesapeake

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here ensures you experience the region’s charm at its best, whether you prefer peaceful off-season stays or lively peak periods for your getaway.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, you'll experience warm weather ideal for outdoor activities and exploring the region's natural beauty. This is when demand for vacation rentals increases as visitors seek to enjoy the area's lakes and parks.

Average Temperature Daytime: 85°F - Nighttime: 65°F
autumn
Fall (September to November)

The fall season offers pleasant temperatures and vibrant autumn foliage that enhances your stay here. It's a popular time for those seeking scenic beauty and comfortable weather in vacation accommodations.

Average Temperature Daytime: 70°F - Nighttime: 50°F

Off-Season Highlights

image
Winter (December to February)

In winter, the area experiences cooler temperatures, making it ideal for travelers seeking quieter times and cozy stays in vacation rentals. The off-peak period often provides better deals and more availability.

Average Temperature Daytime: 40°F - Nighttime: 25°F
image
Spring (March to May)

Spring brings milder weather and blossoming scenery, perfect for exploring without the crowds. This shoulder season can offer a peaceful retreat with opportunities for affordable bookings in vacation rentals.

Average Temperature Daytime: 60°F - Nighttime: 40°F

Weekly Weather Forecast for Chesapeake

How to Book Your Chesapeake Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Chesapeake

More Top-Rated Vacation Rentals in Chesapeake Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining with a fully equipped patio or barbecue area, perfect for evening gatherings.
  • Take advantage of private yards or gardens to unwind and soak up the peaceful surroundings.
  • Make use of outdoor pools or hot tubs available in some properties for relaxing after a day of exploring.
  • Benefit from scenic walking trails or biking paths nearby that showcase the natural beauty of the area.
  • Relax on spacious decks or porches while enjoying the fresh air and picturesque views.
  • Utilize outdoor fire pits for cozy evenings and making memories under the stars.
  • Access private waterfronts or lakeside areas for fishing, kayaking, or simply appreciating the tranquil waters here.

Top Attractions Around Chesapeake

What attractions are nearby?

Nearby, you can explore a variety of outdoor activities and local attractions that make this destination perfect for outdoor enthusiasts and leisure seekers alike.

image
image

Family Activities

  • Chesapeake Community Park: Spend quality time outdoors at this scenic park, offering playgrounds, walking trails, and picnic areas for families to enjoy together.
  • Tomlinson Run State Park: Explore hiking trails, nature programs, and a spacious playground in this nearby state park perfect for outdoor family adventures.
  • Heritage Farm Museum & Village: Discover local history through interactive exhibits and outdoor displays that engage children and adults alike.
  • Northwestern Ohio Railroad Museum: Introduce your family to the region’s railroad history with train exhibits and possibly a train ride experience, ideal for curious young explorers.
image

Adult Activities

  • Explore the Ohio River Waterfront Park: Enjoy a relaxing stroll or a picnic along the scenic Ohio River, offering picturesque views and a peaceful atmosphere.
  • Visit the Heritage Village Museum: Discover local history and culture through engaging exhibits and preserved historic buildings reflective of this area's rich heritage.
  • Participate in outdoor activities at Earl Thomas Conley Park: Engage in hiking, biking, or simply unwinding in this expansive park that highlights the natural beauty of the region.
  • Enjoy local cuisine at nearby restaurants: Savor regional flavors and fresh ingredients at dining establishments that showcase the culinary traditions of this area.

Other Places to Stay in Chesapeake, OH

Brentwood
Brentwood Vacation Rentals
More Places to Stay Near Chesapeake

Chesapeake Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Attractions: Discover the area's unique attractions to enrich your stay in Chesapeake, Ohio, and make the most of your visit.
  • Book Early for Best Vacation Rentals: Secure your preferred vacation rental early to ensure availability and enjoy prime amenities in this destination.
  • Plan Outdoor Activities: Take advantage of the region’s outdoor opportunities, from parks to scenic trails, to create memorable experiences here.
  • Check Venue Accessibility: Review the accessibility options of your chosen vacation rentals to ensure a comfortable and convenient stay in this area.

Transportation Options

  • Chesapeake Transit System: This local transit service offers convenient bus routes within the area, making it easy to explore your surroundings without a car.
  • Amtrak Rail Service: Connecting through nearby stations, Amtrak provides comfortable train travel options for those looking to visit neighboring cities or regions from here.
  • Rental Car Services: Numerous rental agencies are available at the regional airport and throughout the area, giving you flexibility and independence during your stay.
  • Taxi and Rideshare Options: Taxi companies and rideshare services like Uber and Lyft operate in this destination, providing quick and reliable transportation for your local movements.

Local Customs Options

  • Southern Hospitality: Embrace the warm and welcoming attitude that is a hallmark of local interactions here.
  • Participate in regional festivals that highlight traditional music, food, and community spirit.
  • Local Cuisine Etiquette: Enjoy the region’s culinary delights while respecting mealtime customs and local dining traditions.
  • Respect for Nature: Practice environmentally conscious habits, as the area values its natural surroundings and outdoor heritage.

Frequently Asked Questions About Chesapeake?

1. What are the top vacation rentals in Chesapeake?

There are a lot of options in Chesapeake. If you plan on staying in the Chesapeake area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chesapeake:

2. How many vacation rentals have private pools in Chesapeake?

There are 1 vacation rentals with private pools near Chesapeake. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Chesapeake are best for families?

If you are looking for a family-friendly vacation home in Chesapeake, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chesapeake:

4. How many Rentbyowner vacation rentals are available in Chesapeake?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 59 in the Chesapeake area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Chesapeake. 

5. What is the cancellation policy for vacation rentals in Chesapeake, Ohio?

The cancellation policy varies by listing. You should review the specific property's cancellation terms on the listing page or contact the property owner directly for detailed information.

6. How do I ensure my booking in Chesapeake is secure and confirmed?

Bookings are officially confirmed once you complete the reservation process and receive a confirmation email from the platform. For added security, verify the listing details and communicate with the owner if needed.

7. Are there any age restrictions or additional requirements when booking a stay here?

Age restrictions and other requirements can differ among properties. Please check the individual listing for any specific criteria or contact the owner for clarification before booking.

8. What amenities are typically included with vacation rentals in this region?

Amenities vary depending on the property, but many rentals offer essentials such as Wi-Fi, parking, and kitchen facilities. You can view the available amenities on each listing page to find a place that suits your needs.

9. Is there a minimum stay requirement for booking in Chesapeake, Ohio?

Minimum stay policies depend on the property owner and the listing. Details about the minimum nights required are available on the property listing or can be confirmed by reaching out to the owner directly.