Cheapside Holidays

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Where to stay in Cheapside

Find the best Cheapside areas and neighborhoods for the activities you enjoy most. Learn more about Cheapside

A town with historic buildings, a prominent church with a tall steeple, and a river in the background.

Historic Downtown Cape Charles

1 out of top 10 points of interest in this area

While visiting Historic Downtown Cape Charles, you might make a stop by sights like Cape Charles Beach and Central Park.

An aerial shot of abandoned concrete ships from World War II

Kiptopeke

While visiting Kiptopeke, you might make a stop by sights like Kiptopeke State Park and Chesapeake Bay.

A coastal town with a bridge over a river, surrounded by residential buildings and greenery.

Picketts Harbor

Picketts Harbor might not have many top sights, but Kiptopeke State Park and Bay Creek Golf Club are two attractions nearby that you can check out.

A pier extending into a greenish sea with rocky shore in the foreground.

Tower Hill

Tower Hill might not have many top sights, but Oyster Farm Marina and Central Park are two attractions nearby that you can check out.

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

Bay Ridge

While there might not be top attractions in Bay Ridge, you can explore the larger area and discover places like Bay Creek Golf Club and Kiptopeke State Park.

Top hotels in Cheapside

Shore Stay Suites

26406 Lankford Hwy Cape Charles VA

Fully refundableReserve now, pay when you stay

£106

1 Sept - 2 Sept

includes taxes & fees

8.2/10 Very good! (702 reviews)

"Air conditioner was annoying 😑 kicked on and off about every 15 or so minutes 🙄. Bathroom has mold in shower, no grab handles in shower for those that need one Not worth $240 a night."

Reviewed on 7 Aug 2026

Beachfront Estate, Multi-Level Decks, Bay Creek

Cape Charles VA

9/10 Wonderful! (4 reviews)

"Beautiful home and amazing views! We had a wonderful trip and Cape Charles is charming! Loved the amenities of the pool/gym and the ease of getting around on golf carts. We will definitely be back!"

Reviewed on 1 Aug 2026

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Cape Charles Milestone Lodge

23054 Lankford Hwy. Cape Charles VA

4/10 (2 reviews)

"No fancy… Yet. This place has so much potential. It’s close to Cape Charles and Eastville and had everything we needed. Again, not fancy but our room had space and an awesome AC and pretty good water pressure."

Reviewed on 16 Jul 2026

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See all 393 properties in Cheapside

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.