Cheapside Vacations from $495
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The Latest Cheapside Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Boardwalk Resort and Villas
Northeast Virginia Beach
Save 100% on your flight
Price was $896, price is now $495 per person
$495
per person
May 15 - May 20
found 15 hours ago
Roundtrip flight included
Hartford (BDL) to Norfolk (ORF)
8.6/10 Excellent! (1,003 reviews)
Everything is wonderful!
Beautiful area
Quiet nice area and the staff are wonderful!
Reviewed on Apr 9, 2026
Sea Ranch Resort
Save 100% on your flight
Price was $1,389, price is now $858 per person
$858
per person
Jul 5 - Jul 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
8.6/10 Excellent! (1,001 reviews)
Sofa was quite old and uncomfortable. Adequate common area. Nice indoor pool
Reviewed on Apr 10, 2026
Pamlico Station Edgecamp
South Rodanthe
Save 100% on your flight
Price was $2,137, price is now $1,366 per person
$1,366
per person
Jul 5 - Jul 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
9.4/10 Exceptional! (27 reviews)
We came out for our anniversary and had a wonderful time! The sauna and cold plunges were being repaired, which was disappointing, but understandable to service them in the off season. It was quiet and very relaxing and our text to the concierge was very quick!
Reviewed on Mar 30, 2026
John Yancey Oceanfront Inn
Save 100% on your flight
Price was $1,573, price is now $1,006 per person
$1,006
per person
Jul 5 - Jul 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
9/10 Wonderful! (1,865 reviews)
This is our second time staying at John Yancy. Its nothing fancy but it has a great breakfast with a beautiful gazebo to eat at if you choose. Staff is nice. My biggest complaint was the wifi connection at night. It kept buffering or disconnecting which made it frustrating with little ones.
Reviewed on Apr 9, 2026
Ocean 27
Northeast Virginia Beach
Save 100% on your flight
Price was $2,393, price is now $1,622 per person
$1,622
per person
Jun 23 - Jun 27
found 7 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Norfolk (ORF)
6.4/10 (1,059 reviews)
Close to beach. Ground level beach access rooms. Grounds need to be picked-up a bit. Centrally located along boardwalk.
Reviewed on Oct 13, 2025
Where to stay in Cheapside
Find the best Cheapside areas and neighborhoods for the activities you enjoy most. Learn more about Cheapside
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.
Cheapside Hotel Deals
Shore Stay Suites
26406 Lankford Hwy Cape Charles VA
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $129 total per night from Apr 13 to Apr 14
$129 total
Apr 13 - Apr 14
Total with taxes and fees
8.4/10 Very Good! (661 reviews)
.
Reviewed on Apr 2, 2026
The Captains Quarters located in Cape Charles, VA offers breathtaking views.
Cape Charles VA
$314 nightly
The price is $357 total per night from Apr 13 to Apr 14
$357 total
Apr 13 - Apr 14
Total with taxes and fees
9.8/10 Exceptional! (43 reviews)
Relaxing and quiet
Reviewed on Mar 22, 2026
The Baywood Bed & Breakfast
31400 Latimers Bluff Rd Cape Charles VA
$223 nightly
The price is $248 total per night from Apr 13 to Apr 14
$248 total
Apr 13 - Apr 14
Total with taxes and fees
9.8/10 Exceptional! (196 reviews)
Beautiful setting, wonderful breakfast, lovely hosts!
Reviewed on Oct 29, 2025
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.
Discover the most popular places to visit in Cheapside
Cape Charles Beach
4.5/5(31 reviews)
Why not spend a carefree afternoon at Cape Charles Beach during your travels in Cape Charles? Wander the parks or discover the sunsets in this relaxing area.
Kiptopeke State Park
4/5(27 reviews)
You can take time to visit Kiptopeke State Park during your travels to Cape Charles. Wander the beautiful beaches in this relaxing area.
Eastern Shore of Virginia National Wildlife Refuge
4.5/5(14 reviews)
Explore the great outdoors at Eastern Shore of Virginia National Wildlife Refuge, a lovely green space in Cape Charles. Wander the beautiful beaches in this relaxing area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.