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.
Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
Save 100% on your flight
per person
Sep 6 - Sep 10
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
This hotel features a gym and a seasonal outdoor pool. There's fun for all ages with a children's club and mini golf, and families will appreciate the onsite laundry facilities. Enjoy the hot tub and perks like free self parking and free WiFi.
The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
Save 100% on your flight
per person
Sep 6 - Sep 10
found 23 hours ago
Roundtrip flight included
Boston (BOS) 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.
Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Save 100% on your flight
per person
Sep 6 - Sep 10
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
A golf course, a full-service spa, and 3 outdoor pools are all featured at this smoke-free hotel. Traveling on business? Take advantage of the express check-out and WiFi in public areas. You'll also find 6 outdoor tennis courts and an indoor pool.
Barsala At Sphere Apartments

Barsala At Sphere Apartments

3.5 out of 5
Save 100% on your flight
per person
Sep 6 - Sep 10
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
This aparthotel includes free WiFi in public areas and a virtual front desk.
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
per person
Sep 6 - Sep 10
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
This Colonial resort features 2 outdoor tennis courts, an outdoor pool, and a restaurant. Bring the family and enjoy the mini golf, children's pool, and arcade/game room. Enjoy the indoor pool and perks like free self parking and free WiFi.

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 water park, a garden, and laundry facilities. Barbecue grills are provided for your convenience.
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
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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
Free Cancellation
Reserve now, pay when you stay
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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
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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
Camp Cardinal Gloucester Point

Camp Cardinal Gloucester Point

2.5 out of 5
3149 Campground Rd, Hayes, VA
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This cabin doesn't skimp on freebies - guests receive free WiFi and free self parking. Bring the family and enjoy the waterslide, playground, and arcade/game room. A seasonal outdoor pool is also provided.
Pool
Pet friendly
Oceanfront White Stone Cottage w/ Private Beach!

Oceanfront White Stone Cottage w/ Private Beach!

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This cottage features barbecue grills.
Kitchen
Pet friendly
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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 $317. 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

Browse Gwynn vacation photos for more inspiration