Cheapside Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence
Better together
Save up to CA $4,200 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Cheapside

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

Comfort Suites Airport

Central Newport News

CA $1,187

per person

Dec 12 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Norfolk (ORF)

8.8/10 Excellent! (1,170 reviews)

Pool was amazing

Reviewed on Oct 26, 2026

Beach Walk

Downtown Ocean City

CA $2,976

per person

Dec 8 - Dec 12

just found

Roundtrip non-stop flight included

Montreal (YUL) to Salisbury (SBY)

7.6/10 Good! (126 reviews)

We never slept here. The room was incredibly dirty. Stained sheets, stained carpet, god only knows what on the walls in the bathroom. The table and chairs were a table that folded out from the wall with a stick underneath. The chairs were two rusty folding chairs. The blinds in the window were busted up and only covered half the window. I honestly don’t know how they’ve not been shut down. We quickly found another hotel.

Reviewed on Oct 13, 2026

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

Residence Inn by Marriott Norfolk Airport

CA $1,287

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Norfolk (ORF)

8.4/10 Very good! (1,000 reviews)

Awesome

Reviewed on Oct 25, 2026

The Inn at Four Eleven York

West Freemason

CA $2,248

per person

Dec 27 - Jan 3

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Norfolk (ORF)

10/10 Exceptional! (114 reviews)

We stayed for our honeymoon before embarking on our cruise to Bermuda out of Norfolk. The port was very close to the Inn. The Inn is beautiful and so romantic. The area around the Inn had several options for dining. The walkable area was so romantic with its old architecture and cobblestone streets. I would love to come and stay longer and experience their restaurants and the city of Norfolk. I would highly recommend the Inn to anyone wanting a place that is not a big box type hotel. If you want charm and romance this place is for you!!!!

Reviewed on Oct 20, 2026

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.