Gloucester Point Vacation Packages

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Top Gloucester Point Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Virginia Beach At The Beach

Days Inn by Wyndham Virginia Beach At The Beach

2 out of 5
Northeast Virginia Beach
per person
Sep 3 - Sep 7
found 2 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Norfolk (ORF)
7.6/10 Good! (1,020 reviews)
The rooms can get an upgrade, the room description on Expedia is not accurate as expedia cited a kitchenette which was not there , AC was working but leaking, the staff are all nice and friendly, small bathroom with some plumping issues.

Reviewed on Aug. 1, 2025

Four Sails Resort

Four Sails Resort

3.5 out of 5
Northeast Virginia Beach
per person
Sep 3 - Sep 7
found 2 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Norfolk (ORF)
7.6/10 Good! (36 reviews)
Great balcony with a great view

Reviewed on Aug. 2, 2025

The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

3 out of 5
Northeast Virginia Beach
per person
Sep 3 - Sep 7
found 2 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Norfolk (ORF)
7.8/10 Good! (1,400 reviews)
Fantastic, very professional

Reviewed on Aug. 2, 2025

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3 out of 5
Northeast Virginia Beach
per person
Sep 3 - Sep 7
found 2 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Norfolk (ORF)
8.2/10 Very Good! (1,108 reviews)
Friendly and helpful staff! Great location and clean rooms

Reviewed on Aug. 2, 2025

Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
Northeast Virginia Beach
per person
Sep 3 - Sep 7
found 2 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Norfolk (ORF)
7.6/10 Good! (1,614 reviews)
Pros: Is close to everything you need to create wonderful vacations moments. Staff is friendly. Cons: This hotel really needs serious upgrades starting from refrigerator, AC, rugs and the bathroom. Sometimes you need to share parking with people from outside because the hotel share parking lot for the activities on the beach so everyone have access to elevators and others areas of the hotel.

Reviewed on Aug. 3, 2025

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Gloucester Point Hotel Deals

Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 out of 5
3601 Ironbound Rd, Williamsburg, VA
Fully refundableReserve now, pay when you stay
The price is CA $115 per night from Aug 12 to Aug 13
CA $115
CA $171 total
Aug 12 - Aug 13
includes taxes & fees
8.8/10 Excellent! (2,884 reviews)
"Everything was good but the rain flooded the parking lot and I had to run out in the rain and move my car across the street to higher grounds. I also didn't like that the patio door was locked and I was not provided a key to go out. That was not safe."

Reviewed on Aug. 1, 2025

Hilton Vacation Club The Historic Powhatan Williamsburg
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
105 Visitors Center Dr, Williamsburg, VA
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Aug 20 to Aug 21
CA $157
CA $208 total
Aug 20 - Aug 21
includes taxes & fees
8.8/10 Excellent! (1,486 reviews)
Best place to stay while visiting Williamsburg
"Very comfortable and quiet suite with king size bed right next door to the historic town. Good rates. So-so breakfast but still respectable. Charging spot for your EV but bring your own lockable charging cable."

Reviewed on Aug. 2, 2025

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
4870 Longhill Road, Williamsburg, VA
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Aug 5 to Aug 6
CA $122
CA $155 total
Aug 5 - Aug 6
includes taxes & fees
8.6/10 Excellent! (1,596 reviews)
"This Property was perfect for my family and I. It was 3 teens and 2 adults it was more than enough space for us. The pool, was nice the game room was a little small and the games needed repairing. They were out of service."

Reviewed on Aug. 4, 2025

Vacation Village At Williamsburg
See all 2,216 properties in Gloucester Point
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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What to do in Gloucester Point

See these Tall Ships up close!

Jamestown Settlement American Revolution Museum 7-Day Ticket

CA $40
per adult
88% of travellers recommend
Jamestown Settlement American Revolution Museum 7-Day Ticket
Williamsburg: The Patriots Historical Walking Tour

Williamsburg: The Patriots Historical Walking Tour

CA $34
per adult
Williamsburg: The Patriots Historical Walking Tour
Patriots Tour of Colonial Williamsburg or Williamsburg 101

Patriots Tour of Colonial Williamsburg or Williamsburg 101

CA $34
per adult
Patriots Tour of Colonial Williamsburg or Williamsburg 101
See all activities in Gloucester Point

Frequently asked questions

How much does a Gloucester Point vacation package cost?
You'll find cheap prices from CA $946 on Expedia for your Gloucester Point escape. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Gloucester Point costs.
What are the cheapest months to go to Gloucester Point?
The off-season is the best time to travel to Gloucester Point if you're trying to save. Another tip for finding cheap Gloucester Point vacation packages? Try to avoid visiting during public holidays and any major events.
How many days is enough for Gloucester Point?
Generally, a handful of days is enough to tick off the main attractions during your Gloucester Point vacation. However, if you prefer to have more time to chill out or take day trips, think about extending your trip.
How to find the best Gloucester Point package deals?
Bagging a cheap Gloucester Point package deal is a cinch with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can customize your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Gloucester Point package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Gloucester Point vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component individually. And you'll still get the freedom to create a tailored Gloucester Point vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Gloucester Point?
If you've got your Gloucester Point vacation dates confirmed, book as early as you can to bag some terrific deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Gloucester Point?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Gloucester Point.
  2. Work out your budget: Ensure you have enough money to pay for everything from food and transportation to activities and flights. Your accommodations will likely be the largest expense during your trip to Gloucester Point.
  3. Work out your trip length: Think about how much time you'd like to spend discovering Gloucester Point. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customized Gloucester Point vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.