Deals on vacations and trips to Gwynn

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Gwynn flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

Bluegreen Vacations Parkside Williamsburg, an Ascend Collection Resort

3.5 out of 5
Price was $646, price is now $512 per person
$512
per person
Dec 19 - Dec 22
found 20 hours ago
Roundtrip non-stop flight included
St. Louis (STL) to Richmond (RIC)
This hotel features a gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room. Guests will appreciate free perks like free self parking and WiFi in public areas.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Price was $862, price is now $673 per person
$673
per person
Dec 19 - Dec 22
found 20 hours ago
Roundtrip non-stop flight included
St. Louis (STL) to Richmond (RIC)
2 outdoor tennis courts, an indoor pool, and a lazy river are all featured at this smoke-free hotel. Bring the family and enjoy the free water park, children's pool, and playground. Enjoy the gym and perks like free self parking.
Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
Price was $666, price is now $530 per person
$530
per person
Dec 19 - Dec 22
found 20 hours ago
Roundtrip non-stop flight included
St. Louis (STL) to Richmond (RIC)
A full-service spa, 2 outdoor tennis courts, and an indoor pool are all featured at this Colonial hotel. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking.
Williamsburg Lodge, Autograph Collection

Williamsburg Lodge, Autograph Collection

4 out of 5
Colonial Williamsburg
Price was $830, price is now $695 per person
$695
per person
Dec 19 - Dec 22
found 20 hours ago
Roundtrip non-stop flight included
St. Louis (STL) to Richmond (RIC)
This smoke-free hotel features a golf course, a full-service spa, and 2 restaurants. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the indoor pool and perks like a free area shuttle.
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was $622, price is now $529 per person
$529
per person
Dec 19 - Dec 22
found 20 hours ago
Roundtrip non-stop flight included
St. Louis (STL) to Richmond (RIC)
Free water park access and an outdoor pool are featured at this smoke-free hotel. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the gym and free perks like continental breakfast and free self parking.

Top Gwynn hotels 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

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This cottage features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!

Peaceful Waterfront Retreat. Kayaks, Bicycles, Firepit, and more. Pet-Friendly!

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This vacation home features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG

3.5 out of 5
6639 Forest Hill Ave, Gloucester, VA
Free Cancellation
$116 nightly
The price is $129 total per night
$129 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Hampton Inn Gloucester

Hampton Inn Gloucester

2.5 out of 5
6638 Forest Hill Ave, Gloucester, VA
$110 nightly
The price is $123 total per night
$123 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features an indoor pool and a gym. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking. A 24-hour business center, a coffee shop, and free WiFi in public areas are also on offer.
Pool
Breakfast included
Best Western Kilmarnock Hotel

Best Western Kilmarnock Hotel

2.5 out of 5
599 N Main St, Kilmarnock, VA
Free Cancellation
Reserve now, pay when you stay
$134 nightly
The price is $152 total per night
$152 total
Oct 30 - Oct 31
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the outdoor pool and conveniences like a 24-hour front desk and laundry facilities.
Pool
Breakfast included
Warner Hall

Warner Hall

3 out of 5
4750 Warner Hall Road, Gloucester, VA
$281 nightly
The price is $313 total per night
$313 total
Oct 30 - Oct 31
Total with taxes and fees
This inn features free self parking and free WiFi in public areas. Enjoy the free full breakfast each morning.
Breakfast included
Parking included
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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.

Popular places to visit

Gwynn's Island Musuem

You can spend an afternoon exploring the galleries in Gwynn's Island Musuem during your trip to Piankatank. Amble around the area's marina or experience its festivals.

Gwynn's Island Musuem

Frequently asked questions

How much are vacation packages to Gwynn?
Travelocity has great package deals to Gwynn, including flights and hotels, starting from an impressive $512. With all the money you save, you could book some interesting tours or maybe even tack on a few extra nights to your exciting getaway.
Where can I get the best vacation package deals for Gwynn?
With around 400 air carriers and 1,000,000 hotels across the world, it's hard to top Travelocity. Take advantage of our comprehensive range and score an incredible package deal to Gwynn. Doesn't it feel amazing when planning a trip is that easy?
Why should I purchase my Gwynn vacation package via Travelocity?
By booking your hotel, flights, activities and car rental all in the one place, you'll save big bucks as well as precious time. All our bookings come with an expert team of customer service specialists available 24/7, and you'll know that you'll always be getting the best deal possible with our Price Match Guarantee. So, what are you waiting for? Book the getaway of your dreams today and get packing!
Will I save money on my Gwynn car rental if I bundle it with hotels and flights?
Absolutely — bundle your hotel, car and flight into a Gwynn vacation package and you can save plenty. With so much to uncover in the Gwynn area, that rental vehicle will make exploring easy. Once you've slid into the driver's seat, turn up the tunes and cruise toward White House, an unmissable attraction roughly 100 mi from Gwynn.
What is the best time of year to go to Gwynn?
March, July and August are the most popular months to visit, while November, December and January are typically less busy. If your budget is a little tight, think about visiting around . is usually the most expensive time to drop by.
Which airport is best for Gwynn?
Norfolk Intl. Airport (ORF) is a major hub. You'll find it approximately 45 mi south of Gwynn. Other options worth checking out are Richmond Intl. Airport (RIC) (55 mi away from central Gwynn) and Newport News - Williamsburg Intl. Airport (PHF) (30 mi away from central Gwynn).
What is there to do in Gwynn?
Click away at the excellent photo-ops at Gwynns Island Musuem, one of the most renowned attractions in Gwynn. There's plenty more to uncover around this exciting city, so make sure you have enough time to experience some of its hidden gems.
Where should I stay when visiting Gwynn?
Many people opt to check in to the Island Cottage Getaway With Deck And Shared Pier On The Water. It's an excellent base for your Gwynn vacation.

Photos of local treasures

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