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.
Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
Downtown Richmond
Price was $471, price is now $385 per person
$385
per person
Jul 30 - Aug 1
found 1 day ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. There's a rooftop terrace on site, and a 24-hour front desk and a terrace are also provided.
Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
Midtown
Price was $878, price is now $698 per person
$698
per person
Jul 3 - Jul 5
found 9 hours ago
Roundtrip flight included
Philadelphia (PHL) 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.
Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was $844, price is now $671 per person
$671
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
This smoke-free hotel features a golf course, a full-service spa, and a marina. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Bring the family and enjoy the lazy river, children's pool, and waterslide.
King’s Creek Resort by Spinnaker

King’s Creek Resort by Spinnaker

4.5 out of 5
Price was $760, price is now $624 per person
$624
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
New York (NYC) to Richmond (RIC)
2 outdoor pools, 2 outdoor tennis courts, and an indoor pool are all featured at this luxury aparthotel. There's fun for all ages with mini golf and express theme park tickets, and barbecue grills are available on site. Enjoy the gym and perks like free self parking.
Club Wyndham Kingsgate

Club Wyndham Kingsgate

3 out of 5
Price was $655, price is now $539 per person
$539
per person
Jun 29 - Jul 3
found 18 hours ago
Roundtrip flight included
New York (NYC) 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 playground. Enjoy the indoor pool and perks like free self parking and free WiFi.

Top Gwynn hotels deals

Gwynn's Island Cottage - Private Beach: Book your Stay in the Month of May!

Gwynn's Island Cottage - Private Beach: Book your Stay in the Month of May!

Grimstead VA
Get rates
This cottage features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
The Tides Inn

The Tides Inn

4 out of 5
480 King Carter Dr Irvington VA
Free Cancellation
Reserve now, pay when you stay
$287 nightly
The price is $309 total per night
$309 total
May 17 - May 18
Total with taxes and fees
This smoke-free hotel features a private beach, a full-service spa, and a marina. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a children's club and a playground, and families will appreciate the onsite laundry facilities.
On private beach
Pool
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
$114 nightly
The price is $127 total per night
$127 total
May 28 - May 29
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
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
$95 nightly
The price is $106 total per night
$106 total
May 28 - May 29
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
Quality Inn Kilmarnock

Quality Inn Kilmarnock

2.5 out of 5
599 N Main St Kilmarnock VA
Free Cancellation
Reserve now, pay when you stay
$110 nightly
The price is $124 total per night
$124 total
May 31 - Jun 1
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. Enjoy the outdoor pool and conveniences like a 24-hour front desk and laundry facilities.
Pool
Breakfast included
Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset

Cape Charles VA
$323 nightly
The price is $379 total per night
$379 total
May 10 - May 11
Total with taxes and fees
This cottage features laundry facilities.
Washer
Dryer
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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 Museum

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

Gwynn's Island Museum

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 $385. 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