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A beach at sunset with a pier extending into the water.

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    Check prices for these dates, 14 – 15 December 2026

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    Our top choices for Chesapeake apartments

    1. Great Studio | Pool & Hot Tub. Your Next Vacation

    A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

    2. 1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

    A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

    3. Studio | Free Breakfast. Indoor Pool & Hot Tub.

    A large indoor swimming pool with clear water, surrounded by lounge chairs and potted plants.

    4. Private 1 Bed Apt - Historic Olde Towne Portsmouth

    A narrow brick pathway flanked by two houses with siding.

    5. Guesthouse in ideal location with private entrance

    A modern kitchen with white cabinets, a built-in oven, and a dining area with a gray sofa and a table.

    6. The SEA-renity 11 cozy apartment across from the beach

    A beach with a sunset, calm water, and a few people walking along the shore.

    7. Sojourn's Harborage 9549 unit 1

    A hotel room with a large bed, a bedside lamp, a dresser, and a painting on the wall.

    8. Angie's Guest Cottage

    A two-story house with a white porch, a red door, and a small Christmas tree.

    9. Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

    A glass-top table with two cushioned chairs on a wooden deck, a vase with red flowers, and a brick wall.

    10. Historical Suffolk Loft Apartment in Downtown Area

    Exterior detail

    11. The SEA-renity 12 cozy apartment across from the beach

    A sandy beach with footprints, a clear blue sky, and a distant pier.

    12. SEA-renity 17 cozy apartment across from the beach

    A beach with a sunset, calm water, and a few people walking along the shore.

    13. SEA-clusion 7 cozy apartment across from the beach

    A beach with a sunset, calm water, and a few people walking along the shore.

    14. SEA-clusion 1 cozy apartment across the street from the beach!

    A sandy beach with footprints, a clear blue sky, and a distant pier.

    15. Sojourn's Harborage S

    An outdoor patio with wooden furniture, a fire pit, and a covered area with a view of the surrounding landscape.

    16. The SEA-clusion 8 cozy apartment across from the beach

    A beach with a sunset, calm water, and a few people walking along the shore.

    17. 1866 EOV Dune Suite

    A pathway leading to a beach with a clear view of the ocean and a blue sky.

    18. SEA-Clusion 6 cozy apartment across from the beach

    A modern living room with a sofa, coffee table, and dining area.

    19. SEA-renity 13 cozy apartment across from the beach

    A beach with a sunset, calm water, and a few people walking along the shore.

    20. Sojourn 1 BR Beach Home with Private Beach Access

    A beachfront property with multiple buildings, including a large multi-story structure and several single-story houses, with a sandy beach and ocean in the foreground.

    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.

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    Learn more about Chesapeake

    Explore the Great Dismal Swamp's boardwalk trails where kayakers glide past cypress trees and wildlife thrives. The Chesapeake Arboretum's 48 acres of forests and gardens offer peaceful hiking, while nearby waterfront restaurants serve the bay's famous blue crabs.

    See all hotels in Chesapeake

    A beach at sunset with a pier extending into the water.

    Frequently Asked Questions

    What's it like to stay at an apartment in Chesapeake?

    You can search through 15 apartments in Chesapeake for your stay. Why not enjoy the array of shops and popular beaches in this family-friendly area? Visit top places in the surrounding region such as Naval Station Norfolk and Sandbridge Beach.

    How do you know if an apartment is the right choice for your stay?

    An apartment features a kitchen for convenient meals, and often has more space than a traditional hotel room. Apartments are a good option for couples who want to live like locals, and also for families wanting the conveniences of home.

    What's the best apartment for a stay in Chesapeake?

    Below you'll find a top apartment in the area to consider: Angie's Guest Cottage: Situated in Virginia Beach , 18.1 mi/29.1 km from the heart of Chesapeake.

    How many apartments should I expect to find in Chesapeake?

    Expedia has 15 apartments to book in Chesapeake.

    What can I expect from the weather when I travel to Chesapeake?

    Weather is only one factor, but it can really affect your travel plans, especially when you're planning an extended stay in Chesapeake. The hottest months are usually July and August, with an average temperature of 25°C, while the coldest months are January and February, with an average of 7°C. Average annual precipitation for Chesapeake is 1359 mm.

    What are the must-see places to visit in Chesapeake?

    Chesapeake is well regarded for its beaches and shops. Family-friendly attractions include Broadmoor Play Area and Parkview Play Area, whereas Chesapeake City Park and Oak Grove Lake Park are a couple of great spots to enjoy the outdoors. Other popular places to visit in the area include Naval Station Norfolk and Sandbridge Beach.

    What's the best way to get to and around Chesapeake?

    Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Norfolk, VA (ORF-Norfolk Intl.), which is located 10.1 mi (16.3 km) away from the heart of the city. You can also search for flights into Newport News, VA (PHF-Newport News - Williamsburg Intl.), which is 27.6 mi (44.5 km) away. If you'd like to explore around the area, you may want a rental car for your journey.