Gwynn Vacation Packages

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Your Gwynn Vacation

Enjoy amazing adventures when you book a vacation package to Gwynn. Whether you're a foodie, history buff or just a traveler who loves discovering new places, there's something for everyone in this interesting city. Need some inspiration on what to do or see first during your trip to Gwynn? Check off well-known attractions such as Gwynns Island Musuem. Stop daydreaming and start doing. Check out the wide range of options on Expedia today and finally put your Gwynn vacation plans into gear!

Top Gwynn Vacation Deals

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

The Commonwealth

4 out of 5
Downtown Richmond
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Richmond (RIC)
9/10 Wonderful! (1,247 reviews)
Very central location right behind the state capitol. Room was great incl fridge & microwave. There's only valet parking (~$45/night extra), but they're pretty quick once you request your car. It's definitely a renovated older building, because the elevators are TINY.

Reviewed on Jul. 4, 2025

Warner Hall

Warner Hall

3 out of 5
Save 100% on your flight
per person
Aug 21 - Aug 28
found 5 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Richmond (RIC)
10/10 Exceptional! (6 reviews)
A gorgeous great house with over 350 years of history. The staff are absolutely wonderful. They make sure you want for nothing. And breakfast is delicious!

Reviewed on May 7, 2025

The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Save 100% on your flight
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
9/10 Wonderful! (1,008 reviews)
I am an owner and was just staying for 1 night. The room was not ready when I arrived at 4pm.

Reviewed on Jul. 2, 2025

Williamsburg Lodge, Autograph Collection

Williamsburg Lodge, Autograph Collection

4 out of 5
Colonial Williamsburg
per person
Aug 21 - Aug 28
found 5 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Richmond (RIC)
9/10 Wonderful! (1,001 reviews)
Within easy walking distance of all of “ Williamsburg sites. Excellent breakfast! A lot of the charm of the Inn but much less expensive… we’ve stayed at both.

Reviewed on Jun. 30, 2025

Williamsburg Inn, an official Colonial Williamsburg Hotel

Williamsburg Inn, an official Colonial Williamsburg Hotel

5 out of 5
Colonial Williamsburg
Save 100% on your flight
per person
Sep 21 - Sep 27
found 6 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.8/10 Exceptional! (283 reviews)
Unique, charming, and clean. Staff was very friendly and helpful. We ate dinner and breakfast at the restaurant on property and both were delicious. There is a nice pool, and the back patio was fun for the kids, with cornhole and a giant chess set. Bonus points for the easy walk into colonial Williamsburg.

Reviewed on Jul. 2, 2025

Ready to book your vacation to Gwynn?

 

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Gwynn Hotel Deals

Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water
Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water
Grimstead
10/10 Exceptional! (186 reviews)
Second year
"Just as pleased as the first year"

Reviewed on Jun. 17, 2025

Get rates
Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water
Holiday Inn Express Gloucester by IHG
Holiday Inn Express Gloucester by IHG
3.5 out of 5
6639 Forest Hill Ave, Gloucester, VA
Fully refundable
The price is CA $151 per night from Jul 6 to Jul 7
CA $151
CA $168 total
Jul 6 - Jul 7
includes taxes & fees
7/10 Good! (615 reviews)
"Sunday we didn't have hot water so we couldn't take showers."

Reviewed on Jun. 30, 2025

Holiday Inn Express Gloucester by IHG
Oceanfront White Stone Cottage w/ Private Beach!
Oceanfront White Stone Cottage w/ Private Beach!
White Stone
7.4/10 Good! (67 reviews)
Cute White Stone water house
"The house was perfect for me, my husband and dog! We enjoyed being so close to the water. Its close enough to town but far enough way to feel secluded."

Reviewed on May 4, 2025

Get rates
Oceanfront White Stone Cottage w/ Private Beach!
See all 338 properties in Gwynn
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Gwynn vacation package cost?
Offering excellent value package deals from CA $639 on Expedia, you'll be surprised at how little a vacation to Gwynn costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Gwynn?
If you're hoping to book a cheap Gwynn vacation package, consider travelling in January, February and November. You'll usually find lower prices on hotels and flights during these quieter months --- ideal for travellers wishing to save money.
How many days is enough for Gwynn?
To get the most out of your Gwynn vacation, we suggest staying for 3 days. Split your time between discovering Deltaville Maritime Museum, Holly Point Nature Park and other must-see attractions, in addition to experiencing neighbourhoods like Piankatank and Moon. If you've got some spare time, add a tour or day trip to your Gwynn vacation itinerary.
How to find the best Gwynn package deals?
Begin your search for a Gwynn package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Gwynn package deal right away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Gwynn escape underway.
Is it cheaper to book a Gwynn vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component separately. And you'll still get the flexibility to create a customized Gwynn vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Gwynn?
Secure incredible bargains by reserving your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Gwynn escape.
How to plan a trip to Gwynn?

  1. Choose when to travel: Check your diary and get your bags packed. Your favourite season and the type of activities on offer will also help you decide when to vacation in Gwynn.
  2. Budget wisely: On top of the cost of your hotel, you'll need to factor in other expenses too. These include food, flights and transportation. Also, set aside a little extra for unexpected costs that may crop up during your trip to Gwynn.
  3. Determine how many days away: Start by listing all the activities and sights you'd like to get to in Gwynn. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a customized Gwynn vacation package.

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