Located along the Intracoastal Waterway on Virginia’s Atlantic coast, Chesapeake boasts a host of other extensive waterways ranging from lakes to rivers and canals. Relax in a charming house rental, or one of the city's many condo rentals, and experience numerous outdoor activities such as birdwatching and hiking. If you choose to stay in the city, museums and diverse dining options abound.
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Best Vacation Home Deals in Chesapeake
Find a vacation rental fitting your expectations among the 647 great accommodations from numerous providers in Chesapeake. HomeToGo, a vacation rental search engine, instantly compares all of these offers so you can save up to 71%!
Top-Rated Rentals and Accommodations in Chesapeake
Recommended Vacation Rentals in Chesapeake
Find your perfect vacation rental in Chesapeake: from $66 per night
Budget-friendly Vacation Rentals in Chesapeake
Apartments and vacation rentals with a kitchen
Cook up a feast on your next vacation and book a Chesapeake rental with full kitchen.
Vacation rentals with Wi-Fi
Stay connected while traveling and book a Chesapeake accommodation with high-speed internet.
Vacation rentals and apartments with air conditioning
Keep cool during your trip to Chesapeake and book a vacation rental with air conditioning.
Popular Rental Amenities in Chesapeake
Nearly half of the rentals offer a pool, which makes Chesapeake an excellent vacation destination for people looking to spend vacation poolside. Additionally, more House rental have pools than any other property type. They are an excellent choice if you go in a group of 8, as that is the number of people they can usually accommodate. If you would also like to be close to the water, a few of the rentals providing a pool are located within 2 miles of the waterfront.
Waterfront Vacation Rentals in Chesapeake
Want to find an incredible beachfront rental in Chesapeake?
Try out the 'distance to water' filter during your search and see only the best beach houses for your vacation. You can choose from a number of home rentals in Chesapeake that are located within walking distance from the coast. From dog-friendly rentals by the beach to waterfront cabins with pools, the perfect accommodation in Chesapeake is out there - discover it now via HomeToGo.
7-Day Weather Forecast in Chesapeake
What to Eat in Chesapeake
No matter what you want to eat and drink, Chesapeake has a little bit of everything to delight your taste buds. Wicker’s Crab Pot Seafood is the place in town to savor ocean delicacies. Favorites include the crab dip, blackened tuna tacos, and oysters served with drawn butter.
Modern and stylish, The Butcher’s Son is ideal for romantic dates. Start your gastronomic experience with some seafood nachos or honey mesquite pork belly, before moving on to delicious cuts of humanely raised, hormone-free beef and tasty salads. There's also event rooms for larger groups.
For tasty sandwiches, burgers, and soups in a homey setting, Pop’s Diner is a great pick. The friendly staff here make delectable specialty sandwiches, with turkey, cranberry, and brie on a buttered croissant the most popular. Breakfasts are fantastic here—try their blueberry pancakes.
Unique Local Art and Culture
Chesapeake has a lively artistic and cultural scene. If you like having a hand in your art, then head to AR Workshop Chesapeake. It’s a family-friendly studio that offers lessons on how you can create objects such as canvas tote bags and framed signs. All the materials you'll need are available.
Spend a day at the Virginia Museum of Contemporary Art for an extensive collection of art, including paintings, sculptures, photos, and video installations from local and international artists. There's also studio lessons and workshops on photography, painting, and ceramics.
Another interesting museum is the Chrysler Museum of Art in nearby Norfolk. It houses over 30,000 pieces of art, and a working glassmaking studio that's the only one of its kind in the Mid-Atlantic region. Best of all, parking and admission are free.
Fun Activities for the Family
Chesapeake's family-friendly attractions mix nature with urban fun. Take a guided cruise on the local waters from Hampton Roads or Norfolk. It's a great way to enjoy some sunshine and sea breezes. Tours cover various areas and usually focus on the area's maritime heritage.
Visit the Chesapeake Municipal Center's planetarium, and delve into the wonders of the universe. The first of its kind to be built by a public school system, this facility offers an array of free public programs such as telescope observations. Shows on Thursday are free.
The Town Point Park area provides plenty of opportunities for fun. There's plenty of room to play and picnic amidst its spacious lawns and fountains. Visit the Nauticus maritime museum, with the USS Wisconsin battleship moored next to it. In the summer, various open-air concerts and festivals are held here.
What to See and Do in Chesapeake
Chesapeake is blessed with natural beauty in and around the city for the whole family to enjoy. If being out in nature interests you, then check out the Great Dismal Swamp National Wildlife Refuge. You'll come into contact with numerous species of wildlife including butterflies, red foxes, and flying squirrels.
Head to the Chesapeake Arboretum to marvel at the staggering number of trees on site. Relax on the green grass, or take a self-guided tour on the trails as you commune with nature. A propagation nursery and greenhouse provide glimpses of the ongoing conservation efforts here.
The Northwest River Park along Indian Creek Rd provides a break from urban life, with its nature reserve and fantastic recreational facilities. Whether you want to swim, fish, or play a round of disc or mini golf, the park has something for everyone to enjoy.
A Variety of Festivals
Chesapeake hosts fabulous family-friendly festivals throughout the year. The Annunciation Greek Orthodox Cathedral hosts the Norfolk Greek Festival in mid-May. Visitors get a taste of Greece through authentic food, traditional Greek dancing, and unique arts and crafts. Tours of the cathedral and its religious icons are also available.
If you’re visiting in early June, Norfolk's Harborfest is a showcase of the region's character. It's one of Virginia's longest-running events, with its renowned Parade of Sail featuring hundreds of military vessels, sailing craft, antique boats, cruisers, and more. Various musical acts and fireworks displays add energy to the festival.
The last week of July is time for the Blue Crab Festival. Organized by the South Norfolk Ruritan Club, this event celebrates the local crustacean delicacy. All-you-can-eat steamed crab, barbecued pork, and various alcoholic and non-alcoholic beverages are part of the spread. There's also live music for this uniquely fun gathering.
Information about vacation rentals in Chesapeake
|🏡 Vacation rentals||647 properties|
|💳 Possible discounts||up to 71%|
|🌙 Nightly prices starting at||$66|
|⭐ Popular amenities||Internet, TV and Air conditioning|
|🐾 Pet friendly accommodations||68 properties|
|🏊 Vacation rentals with pools||344 properties|
Frequently Asked Questions
What is the nightly price for a vacation rental in Chesapeake?
The average accommodation in Chesapeake is priced at $66 per night. If you would like to stay in a house rental, the average price is $376 per night. A apartment rental Chesapeake will cost $214 per night on average.
How many vacation homes are available for booking in Chesapeake?
There are 647 rentals in Chesapeake to browse and book for your next trip.
What amenities are most popular for vacation rentals in Chesapeake?
Usually travelers search for TV, Internet, and Air conditioning when booking a vacation rental in Chesapeake.
How many vacation homes with a pool are in Chesapeake?
Browse 344 vacation rentals available in Chesapeake.
Are dogs allowed in vacation rentals in Chesapeake?
Absolutely, currently there are 68 rentals in Chesapeake that allow pets , with an average nightly rate of $219.
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