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

Cottages in Chesapeake

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Recommended hotels in Chesapeake

A modern hotel with a prominent 'aloft' sign, large glass windows, and a colorful ceiling design.

A modern hotel lobby with a central seating area, a reception desk, and a staircase leading to an upper level.

An outdoor seating area with cushioned benches, a fire feature, and ambient lighting.

A modern bar area with a neon sign, a fireplace, and a seating area with sofas and ottomans.

1. Aloft by Marriott Chesapeake

Greenbrier

$99

$116 total

includes taxes & fees

Oct 4 - Oct 5

A Hampton Inn & Suites building with a beige facade, a red entrance, and a clear blue sky.

A hotel room with two beds, a desk with a chair, a flat-screen TV, a mirror, and a bedside lamp.

A large indoor swimming pool with a sunlit floor, a reception desk, and a seating area with chairs.

A hotel lobby with multiple seating areas, including sofas, chairs, and round tables. There are wall-mounted lamps, a television, and framed pictures on the walls.

2. Hampton Inn & Suites Chesapeake-Battlefield Blvd.

Greenbrier

$110

$128 total

includes taxes & fees

Oct 14 - Oct 15

A modern dining area with wooden flooring, yellow and blue chairs, and a central island with a coffee machine.

A hotel room with a bed, a desk, a chair, a sofa, and a small table.

A modern lobby with a wooden reception desk, seating area, and a vending machine.

3. Comfort Suites Chesapeake - Norfolk

Greenbrier

$95

$111 total

includes taxes & fees

Oct 4 - Oct 5

A Holiday Inn Express hotel with a covered entrance, outdoor lighting, and a landscaped area with plants.

A hotel room with two beds, a desk with a chair, a TV, and a window with a city view.

A buffet with labeled containers of omelets and other dishes.

A bathroom with a white tiled wall, a sink with a mirror, and a shower with grab bars.

4. Holiday Inn Express Chesapeake - Norfolk by IHG

Chesapeake

$110

$129 total

includes taxes & fees

Oct 11 - Oct 12

A Fairfield by Marriott hotel with a modern design, featuring a covered entrance and a prominent sign.

A hotel room with a large bed, a desk with a chair, a small table, and a lamp.

A swimming pool with lounge chairs and umbrellas, surrounded by a building with large windows and a balcony.

A modern kitchen with a central island, bar stools, pendant lighting, and a large wall-mounted artwork.

5. Fairfield Inn and Suites By Marriott Chesapeake

Greenbrier

$109

$128 total

includes taxes & fees

Oct 1 - Oct 2

A modern hotel building with a prominent sign for Delta Hotels Marriott.

An indoor swimming pool with clear glass walls, white lounge chairs, and a tiled floor.

A gym with treadmills, weight machines, and dumbbells.

A modern kitchen with a breakfast bar, various food containers, and a 'PANTRY' sign.

6. Delta Hotels by Marriott Chesapeake Norfolk

Chesapeake

$106

$124 total

includes taxes & fees

Sep 28 - Sep 29

A hotel with a modern design, featuring a prominent entrance with a covered area and a clear sky in the background.

An indoor swimming pool with blue-tiled walls, seating areas, and potted plants.

A modern restaurant with a central bar area, multiple seating options including high tables and bar stools, and a flat-screen TV mounted on a wooden panel.

7. SpringHill Suites by Marriott Chesapeake Greenbrier

Greenbrier

$104

$121 total

includes taxes & fees

Sep 20 - Sep 21

A hotel exterior with a 'tru by Hilton' sign, a parking area, and a fire lane.

A hotel room with two beds, a desk, a chair, and a large window offering a view of trees.

A modern office space with a herringbone-patterned carpet, multiple seating areas with colorful geometric cushions, and a large window providing a view of the outside.

A modern hotel lobby with a curved reception desk, seating area, and a large digital screen.

8. TRU by Hilton Chesapeake, VA

Greenbrier

$98

$116 total

includes taxes & fees

Oct 1 - Oct 2

A modern Hyatt Place hotel with a covered entrance, a parking area, and a landscaped garden.

A modern lobby with a curved wall, seating area, and a fireplace.

A hotel bathroom with a glass shower door, a sink with a granite countertop, and a mirror above the sink.

A bar area with a counter, a beverage dispenser, and several bar stools.

9. Hyatt Place Chesapeake

Greenbrier

$118

$138 total

includes taxes & fees

Sep 27 - Sep 28

A Wingate by Wyndham hotel with a modern design, featuring a green and white color scheme, multiple windows, and a covered entrance.

A hotel room with a gray sofa, a small table, a lamp, a patterned carpet, and a wooden desk with a lamp.

A hotel room with a large bed, a desk, a chair, a television, and a small trash can.

10. Wingate by Wyndham Chesapeake

Chesapeake

$90

$106 total

includes taxes & fees

Oct 12 - Oct 13

A multi-story hotel with a modern design, featuring a parking lot with several cars.

A modern hotel exterior with outdoor seating, a covered patio, and a car parked nearby.

A modern gym with treadmills, a stationary bike, and dumbbells.

A modern dining area with a wooden table and chairs, a counter with a plant, and a view of the street through large windows.

11. Hyatt Studios Chesapeake

Greenbrier

$144

$167 total

includes taxes & fees

Sep 17 - Sep 18

A hotel lobby with multiple seating areas, including tables and chairs, and a large clock on the wall.

A neatly made bed with white linens, two bedside lamps, a wooden bench, and a framed picture on the wall.

A bathroom with a bathtub, a sink, and a mirror.

A swimming pool with clear water, surrounded by lounge chairs and a safety railing.

12. Hampton Inn & Suites Chesapeake-Square Mall

Chesapeake

$81

$95 total

includes taxes & fees

Sep 29 - Sep 30

A Staybridge Suites hotel with a brick facade, multiple windows, and a parking lot with cars.

A patio area with wicker furniture and a stone fire pit, surrounded by a stone wall and a pool.

A modern kitchen area with a stone wall, a flat-screen TV, a Coca-Cola refrigerator, a coffee machine, and a fruit bowl.

A hotel room with a kitchenette, a dining area, a bed, a TV, and a window with curtains.

13. Staybridge Suites Chesapeake by IHG

Chesapeake

$110

$129 total

includes taxes & fees

Oct 4 - Oct 5

A Hilton Garden Inn with a well-lit entrance and a covered parking area.

A hotel room with two beds, a TV, a desk, and a kitchenette.

A breakfast buffet setup with various food items and a coffee station.

An outdoor patio area with wicker furniture, a round table, and a blue umbrella.

14. Hilton Garden Inn Chesapeake/Greenbrier

Greenbrier

$128

$151 total

includes taxes & fees

Oct 4 - Oct 5

An indoor swimming pool with dolphin murals, a sunroof, and seating areas.

A spacious indoor dining area with multiple tables and booths, large windows, and a fireplace.

A hotel room with a bed, a red sofa, a wooden table, a desk with a chair, and a window with curtains.

15. Comfort Inn & Suites Chesapeake - Portsmouth

Chesapeake

$73

$97 total

includes taxes & fees

Oct 4 - Oct 5

A Courtyard by Marriott hotel with a modern facade, multiple balconies, and a well-lit entrance.

An outdoor seating area with wicker furniture and a central fire feature.

A hotel room with two beds, a desk, a chair, and a large window with curtains.

A compact hotel room with a kitchenette, a seating area with a chair, and a small desk.

16. Courtyard by Marriott Chesapeake

Greenbrier

$114

$133 total

includes taxes & fees

Sep 20 - Sep 21

A hotel with a brick facade, a flat roof, and a large entrance.

An indoor swimming pool with clear water, a reception desk, and a few lounge chairs.

A spacious lobby with a reception desk, green seating, and a large TV screen.

A modern dining area with multiple tables and chairs, a large central table, and a television mounted on the wall.

17. Holiday Inn Express Hotel & Suites Chesapeake by IHG

Western Branch North

$84

$99 total

includes taxes & fees

Oct 4 - Oct 5

A hotel entrance with a sign for Homewood Suites Hilton, featuring a large building with multiple windows and a parking area.

A modern living room with a brick wall, a fireplace, a blue sectional sofa, leather ottomans, and a patterned rug.

A conference room with two Lindevoe computer desks, black office chairs, a clock on the wall, and a wooden panel wall.

A hotel reception area with a reception desk, a coffee machine, and a self-service beverage station.

18. Homewood Suites by Hilton Chesapeake-Greenbrier

Greenbrier

$132

$156 total

includes taxes & fees

Oct 4 - Oct 5

A Fairfield by Marriott hotel with a modern design, a covered entrance, and outdoor seating area.

A modern hotel lobby with a central bar area, seating arrangements, and large windows providing natural light.

An outdoor patio area with stone walls, outdoor furniture, and string lights.

A modern lounge area with a round table, two green armchairs, a beige sofa, and large windows with sheer curtains.

19. Fairfield Inn & Suites by Marriott Chesapeake Suffolk

Western Branch North

$89

$105 total

includes taxes & fees

Sep 28 - Sep 29

A hotel with a prominent entrance, a brick facade, and a clear sky.

An outdoor patio area with brick walls, a fire pit, and outdoor furniture.

A spacious lobby with a fireplace, comfortable seating, and a dining area.

A conference room with a long table, multiple chairs, a sofa, and large windows with blinds.

20. Residence Inn by Marriott Chesapeake Greenbrier

Greenbrier

$135

$157 total

includes taxes & fees

Oct 11 - Oct 12

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Top neighborhoods in Chesapeake

A wooden pier extending into a calm lake, surrounded by dense trees.

A person standing on a boat deck facing a foggy landscape with a ship in the distance and the sun setting on the horizon.

A large building with a prominent arched entrance and a green roof.

A building with a large arched entrance, surrounded by trees and a parking lot.

A building with a large arched entrance, a sign reading "Dillard's," and well-maintained landscaping.

Greenbrier

Greenbrier offers the perfect suburban escape with all the comforts of home. Wander through the leafy Chesapeake Arboretum or hit Greenbrier Mall for some serious retail therapy. Oak Grove Lake Park provides a peaceful spot for afternoon strolls while Chesapeake City Park hosts family-friendly activities. You might catch locals enjoying bowling at Bowlero Chesapeake on weekends. Dining options center around familiar chain restaurants with comfortable, family-friendly atmospheres. Hotels cluster near shopping areas with standard amenities and reasonable rates. A car is essential for getting around this sprawling neighborhood, as public transit is limited and destinations are spread out across typical suburban distances.

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A long bridge extending over a turquoise body of water.

Great Bridge

Great Bridge's historic waterways will captivate history buffs and outdoor enthusiasts alike. The Revolutionary War battlefield offers a fascinating glimpse into America's past, while scenic paths along the Elizabeth River provide perfect spots for afternoon strolls. Families can enjoy fishing from public piers or watching boats navigate the Intracoastal Waterway through the lock system. Local seafood restaurants serve up Chesapeake Bay specialties like fresh crab cakes and oysters. Most attractions require a car to reach, though the neighborhood's wide streets and ample parking make navigation simple. Chain hotels provide comfortable bases for exploring this quiet suburban community with its rich historical roots.

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A long pier extending into the ocean at sunset.

A building with a clock tower, surrounded by pink flowers and greenery.

A building with a sign reading "CHESAPEAKE SQUARE".

Western Branch North

Western Branch North offers a peaceful suburban escape with tree-lined streets and family-friendly vibes. Spend afternoons exploring local parks or challenge friends to a game at Bowlero Western Branch. When you need retail therapy, Chesapeake Square Mall has you covered, while Cinemark provides entertainment for movie buffs. Dining options feature casual American fare at family restaurants scattered along main roads. Most travelers choose vacation rentals in comfortable single-family homes, giving you space to spread out. A rental car is essential for getting around this residential area, as public transit is limited but parking is always plentiful.

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A forest path surrounded by tall trees with autumn leaves.

A city skyline at dusk with illuminated buildings and a calm waterfront.

A coastal cityscape with a large ship docked at a port, modern buildings, and a river.

South Norfolk

South Norfolk's well-preserved buildings transport you back to early 20th century America with its charming maritime and railroad heritage. The neighborhood invites leisurely strolls past Craftsman bungalows and Colonial Revival homes with classic wraparound porches. Between walks through tree-lined streets, check out Portlock Galleries at SoNo or enjoy the peaceful atmosphere of Crestwood Park. This quiet residential area offers authentic Southern comfort food at family-owned diners that won't break the bank. B&Bs in converted historic homes provide personalized service with full breakfast included. Getting around is easiest by car, though the historic core is perfectly walkable with ample free street parking throughout the neighborhood.

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Deep Creek South

Suburban community with a rural touch, Deep Creek is connected to the historic Dismal Swamp Canal, a National Historic Civil Engineering Landmark. Located along the original U.S. Highway 17 route, it offers easy access to nearby attractions.

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Top landmarks in Chesapeake

Greenbrier Mall

8.4/10 (837 reviews)

If you want to give your credit card some exercise, head out to Greenbrier Mall in Greenbrier. Why not take a stroll along the beaches and watch the sunset while you're here?

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Chesapeake Square Mall

8.2/10 (429 reviews)

If you want to give your credit card some exercise, head out to Chesapeake Square Mall in Western Branch North.

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Chesapeake Conference Center

7.8/10 (169 reviews)

Chesapeake Conference Center is worth a visit, located 3.4 mi (5.4 km) from central Chesapeake. Hotels.com travelers also say the area is full of friendly people and has lots of nice beaches.

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A wooden bridge over a calm river surrounded by dense forest.

Chesapeake City Park

8.2/10 (180 reviews)

Chesapeake City Park is worth a pic or two when discovering Greenbrier. Hotels.com travelers also say the area is full of friendly people and has lots of nice beaches.

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Oak Grove Lake Park

7.6/10 (39 reviews)

Oak Grove Lake Park is worth a pic or two when discovering Greenbrier. Hotels.com travelers also say the area is full of friendly people and has lots of nice beaches.

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A solitary tree in a swampy area with water around its base.

Lake Drummond

7.8/10 (12 reviews)

Lake Drummond is 15.2 mi (24.5 km) from central Chesapeake, why not stop by during your stay.

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Dismal Swamp Canal

Deep Creek South is home to Dismal Swamp Canal, so why not stop by during your stay in Chesapeake.

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Chesapeake Arboretum

7.6/10 (76 reviews)

Greenbrier is home to Chesapeake Arboretum, so why not stop by during your stay in Chesapeake. Hotels.com travelers also say the area is full of friendly people and has lots of nice beaches. If you have fun at Chesapeake Arboretum, you'll love Riverwalk Parkway Park and Playground and Parkview Play Area, both located nearby.

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Learn more about Chesapeake

A city of contrasts where urban pleasures meet natural wonders. Catch live music at the Chesapeake Conference Center before exploring the Great Dismal Swamp National Wildlife Refuge's mysterious wetlands. Oak Grove Lake Park offers family-friendly trails where locals fish in peaceful seclusion. The Chesapeake Arboretum's 48 acres showcase native trees along winding paths that feel miles from civilization. Shopping enthusiasts can browse Greenbrier Mall's offerings, though savvy visitors head to local farmers' markets for regional specialties. The city's waterfront areas reveal its maritime heritage, with inlets and waterways that once served as crucial trade routes. Don't miss the wildlife viewing platforms where patient observers spot eagles and herons in their natural habitat.

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About the destination

There's a lot visitors like about Chesapeake, especially its beaches and restaurants. You might find the perfect souvenir at Greenbrier Mall or Chesapeake Square Mall. And while you're here, be sure to stop by Chesapeake Conference Center and Chesapeake City Hall.