Holiday Island Vacations from $218
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The Latest Holiday Island vacation packages
Price found within the past 48 hours. Click for updated prices.
TRU by Hilton Chesapeake, VA
Greenbrier East
Price was $309, price is now $218 per person
$218
per person
Dec 8 - Dec 11
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.6/10 Excellent! (278 reviews)
If you don’t have plates they will not give them to you. Also I asked for an extra blanket and wasn’t given one my son had to go downstairs and get one.
Reviewed on Sep 25, 2025
Boardwalk Resort and Villas
Northeast Virginia Beach
Save 100% on your flight
Price was $657, price is now $413 per person
$413
per person
Nov 8 - Nov 15
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,017 reviews)
It was a cool spot. Just gotta tighten up on the grounds upkeep.
Reviewed on Sep 27, 2025
Beach Quarters Resort
Northeast Virginia Beach
Save 100% on your flight
Price was $654, price is now $411 per person
$411
per person
Nov 8 - Nov 15
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.2/10 Very Good! (1,695 reviews)
The shopping was good. You can walk to most everything you want or take the trolley. The view was awesome. My room however could use some updates and maintenance
Reviewed on Sep 27, 2025
The Sanderling
Save 100% on your flight
Price was $1,139, price is now $767 per person
$767
per person
Nov 8 - Nov 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.8/10 Excellent! (512 reviews)
Staff was excellent!!
1st room not good. Needed maintenance and upkeep. Fan needed dusting. After dinner found ants in bed. Staff moved us to a different room which was better maintained but unfortunately it didn’t have the ocean view.
Beach was beautiful loved the chairs and umbrellas provided. Neat fire pits area. For the costs per night I expect better rooms. Staff surprised me with bottle of champagne and a heartfelt note for my special birthday. It was a nice surprise.
Reviewed on Sep 28, 2025
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See all available trips from Columbus to Holiday Island
View all tripsDiscover the most popular places to visit in Holiday Island
Sound Golf Links at Albemarle Plantation
Enjoy a round of golf in Hertford at Sound Golf Links at Albemarle Plantation. Stroll along the riverfront or visit the churches while you're in the area.
Newbold-White House
Find out about the history of Hertford when you take a trip to Newbold-White House. Stroll along the riverfront or visit the churches while you're in the area.
Jim Catfish Hunter Museum
You can browse the exhibits at Jim Catfish Hunter Museum, a museum with a story of its own, during your travels to Hertford. Amble around the area's riverfront or visit its churches.
Holiday Island Hotel Deals
WaterWinds! Waterfront Private house w/dock, Pet friendly
Hertford
10/10 Exceptional! (87 reviews)
"Great Water View! It really does feel like you're on top of the water. The house was clean and ready for us. The beds were the most comfortable beds we've had in a vrbo. Well stocked, and the fire pit at the water was a bonus."
Reviewed on Sep 2, 2025
Edgewater "The Landing" Coastal 3 bedroom Duplex. Private beach, Relax and enjoy
Hertford
Exactly as We Had Hoped
"Our family take two mini vacations a year. This time we decided to do a non-tourist, non event kind of vacation. This property was perfect. The home was very tastefully decorated, and we enjoyed the host's personal art, which could be seen in every room. The layout of the home and the outside lent ..."
Reviewed on Aug 30, 2017
Tranquility on the Sound
Perquimans County
10/10 Exceptional! (2 reviews)
Tranquilily on the water
"This property was the best equipped location I have ever seen. The kids and younger adults enjoyed the kayaks and all of us enjoyed the cornhole. My granddaughter caught three catfish, one flounder, and two turtles. She was thrilled. I would recommend this to anyone with kids or are kids at heart. ..."
Reviewed on Jun 23, 2024
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.