Chesapeake holiday rentals

We found 54 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Chesapeake that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll find the amenities that you need and want, such as air conditioning and a TV. No matter what you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

  • Peace of mind

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  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Chesapeake getaway

Learn about the unique charm of Chesapeake with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Chesapeake

Are you hoping to discover attractions to visit during your stay? Venture out of your cosy holiday rental and experience everything that makes Chesapeake a fun spot to go on holiday. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Camden Park Amusement Park (4.5 mi / 7.2 km)
  • Sandy Creek Golf Course (14.7 mi / 23.6 km)
  • Diamond Links Golf Club (14.7 mi / 23.6 km)
  • El Haijj Salon & Spa (2.2 mi / 3.6 km)
  • Pump Up The Fun (8.8 mi / 14.2 km)
  • Orchard Hills Golf Club (9.8 mi / 15.8 km)

Exploring the natural landscape of Chesapeake

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Chesapeake is a great place to get outside. Here are a few of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Beech Fork State Park (10.3 mi / 16.6 km)
  • Ritter Park (1.8 mi / 2.9 km)
  • Village of Barboursville Park (8.9 mi / 14.3 km)
  • Central Park (10.3 mi / 16.6 km)
  • Armco Park (12.7 mi / 20.4 km)
  • Petsafe Dog Park (2 mi / 3.2 km)

Travelling to and around Chesapeake

The nearest airport is in Huntington, WV (HTS-Tri-State), located 6.7 mi (10.9 km) from the city centre.

Frequently asked questions

When is the best time to visit Chesapeake for a holiday rental?
April is the most popular month to visit Chesapeake, as the spring blooms bring the area to life, making it a delightful time for outdoor exploration. During this month, temperatures typically range from 10 to 20 degrees Celsius, creating a pleasant climate for activities such as hiking along the scenic trails or enjoying picnics by the Ohio River.The peak travel season in Chesapeake runs from June to August, when families flock to the area for summer activities. This bustling period is ideal for those looking to engage in water sports, visit local parks, or attend community events that celebrate the vibrant culture of the region. Expect a lively option filled with fellow adventurers enjoying the warm weather and outdoor fun.For those seeking a more budget-friendly option, December presents an opportunity to enjoy Chesapeake's tranquillity. While this month may be quieter, it offers a unique charm with festive decorations and a chance to experience the local holiday spirit without the crowds.Ultimately, your choice of when to visit Chesapeake will depend on whether you prefer the lively summer energy or the serene beauty of spring and winter.
Are all fees included in the Chesapeake holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Chesapeake holiday homes with parking?
Stayz offers a wide selection of holiday homes in Chesapeake with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Chesapeake holiday homes?
You can find great discounts on holiday homes in Chesapeake on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Chesapeake holiday home booking on Stayz?
To find Chesapeake holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Chesapeake?
A long-stay holiday home in Chesapeake is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Chesapeake holiday home?
Book your Chesapeake holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chesapeake?
Prices for holiday homes in Chesapeake vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Chesapeake to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.