Cheapside Vacation Packages

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Top Holiday Package Deals in Cheapside

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

Boardwalk Resort and Villas

Northeast Virginia Beach

CA $1,240

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Norfolk (ORF)

8.8/10 Excellent! (1,009 reviews)

The balcony and staff and room were amazing. Thank you for helping e out in such a bind

Reviewed on Oct 26, 2026

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Northeast Virginia Beach

CA $1,375

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Norfolk (ORF)

8.2/10 Very good! (1,447 reviews)

For most of my stay, I did not have any hot water when I wanted it. I could do a sink full of dishes and still not have any hot water. While the pool and jacuzzi were nice, the jacuzzi was not really accessible for someone traveling alone with minor mobility issues

Reviewed on Oct 25, 2026

The Barclay Towers Resort Hotel

Northeast Virginia Beach

CA $1,376

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Norfolk (ORF)

7.8/10 Good! (1,002 reviews)

The Historic Cavalier Hotel and Beach Club, Autograph Collection

Northeast Virginia Beach

CA $2,759

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Norfolk (ORF)

9.4/10 Exceptional! (410 reviews)

Sandcastle Resort On The Beach

Northeast Virginia Beach

CA $1,283

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Norfolk (ORF)

7.8/10 Good! (1,034 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 sunset over a beach with a pier extending into the water.

Bay Ridge

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

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.

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 $147

CA $163 total

Nov 23 - Nov 24

includes taxes & fees

8.2/10 Very good! (745 reviews)

"The room is a good size. The kitchenette is a nice feature. The bed was comfortable. A bit worn overall though. Close to Cape Charles historic district"

Reviewed on Oct 25, 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 Captain's Quarters located in Cape Charles, VA offers breathtaking views.

Cape Charles VA

CA $350

CA $501 total

Oct 29 - Oct 30

includes taxes & fees

9.8/10 Exceptional! (82 reviews)

"Such a cute and cozy place! Perfect for a couple & the marina views were an added touch to our stay. Definitely recommend and would stay again!"

Reviewed on Oct 4, 2026

See all 382 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.