Cheapside Vacation Packages

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Top Holiday Package Deals in Cheapside

Price found within the past 48 hours. Click for updated prices.

Sunrise Inn By OYO Newport News US-60

North Newport News

CA $848

per person

Oct 11 - Oct 17

found 17 hours ago

Roundtrip flight included

Detroit (DTW) to Norfolk (ORF)

5/10 (238 reviews)

John Yancey Oceanfront Inn

CA $1,100

per person

Oct 18 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Norfolk (ORF)

9.2/10 Wonderful! (1,927 reviews)

We loved being on the beach, so beautiful. My only complaint was that the air conditioner was a window unit hanging out on the balcony. It was very noisy and had hot air blowing. Side note: our room was very nice and cool :) The free breakfast was terrific. The Sunrise Cafe lady kept it well stocked and clean. We enjoyed our stay.

Reviewed on Sep 2, 2026

4BR Waterfront Penthouse Pool Views

Sandbridge

CA $2,147

per person

Oct 5 - Oct 9

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Norfolk (ORF)

No reviews

The Shore House

West Ocean City

CA $1,876

per person

Oct 24 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Salisbury (SBY)

6.6/10 (766 reviews)

The Barclay Towers Resort Hotel

Northeast Virginia Beach

CA $1,090

per person

Oct 5 - Oct 9

found 1 day ago

Roundtrip flight included

Detroit (DTW) to Norfolk (ORF)

8/10 Very good! (1,026 reviews)

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

If you're spending some time in Historic Downtown Cape Charles, Cape Charles Beach and Central Park are top sights worth seeing.

An aerial view of a coastal area with a long, narrow breakwater extending into the sea, a sandy beach, and a distant shoreline with sparse vegetation.

Kiptopeke

If you're spending some time in Kiptopeke, Kiptopeke State Park and Chesapeake Bay are top sights worth seeing.

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

Picketts Harbor

While Picketts Harbor isn't home to many top sights, Kiptopeke State Park and Bay Creek Golf Club are some notable places to visit nearby.

A beach with a wooden pier and a gazebo, surrounded by rocks and a few people.

Kings Creek Landing

While there might not be top attractions in Kings Creek Landing, you can explore the larger area and discover places like Oyster Farm Marina and Central Park.

Townsend

While Townsend isn't home to many top sights, Kiptopeke State Park and Eastern Shore of Virginia National Wildlife Refuge are some notable places to visit nearby.

Cheapside Hotel Deals

Shore Stay Suites

26406 Lankford Hwy Cape Charles VA

Fully refundableReserve now, pay when you stay

CA $179

CA $199 total

Sep 3 - Sep 4

includes taxes & fees

8.2/10 Very good! (713 reviews)

"It was conveint, but could use some updating. But was clean."

Reviewed on Aug 31, 2026

Beachfront Estate, Multi-Level Decks, Bay Creek

Cape Charles VA

9.2/10 Wonderful! (5 reviews)

"Beautiful house for our family vacation. Easy walk to the beach. Gorgeous views. Happy to bring our dogs along for the trip."

Reviewed on Aug 23, 2026

Get rates

The Captains Quarters located in Cape Charles, VA offers breathtaking views.

Cape Charles VA

CA $346

CA $493 total

Sep 18 - Sep 19

includes taxes & fees

9.8/10 Exceptional! (73 reviews)

"The view was great and the room would have been great also, except there were hardly any paper products, there was a queen size bed instead of a king size (the host has corrected this error on their listing). The location was fantastic. Really just need a king size bed for my 6'6" hubby, especially ..."

Reviewed on Aug 28, 2026

See all 390 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.