Deals on vacations and trips to Gwynn

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The Berkeley Hotel

The Berkeley Hotel

4 out of 5
Downtown Richmond
Price was $387, price is now $314 per person
$314
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Richmond (RIC)
A restaurant and a bar/lounge are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A terrace, express check-out, and a computer station are also on offer.
Griffin Hotel, an official Colonial Williamsburg Hotel

Griffin Hotel, an official Colonial Williamsburg Hotel

3 out of 5
Colonial Williamsburg
Price was $593, price is now $474 per person
$474
per person
Jan 9 - Jan 12
found 23 hours ago
Roundtrip non-stop flight included
Madison (MSN) 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.
Hilton Richmond Downtown

Hilton Richmond Downtown

4 out of 5
Downtown Richmond
Price was $389, price is now $316 per person
$316
per person
Feb 6 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Richmond (RIC)
This traditional hotel includes 3 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.
A house full of steel balls and games

A house full of steel balls and games

2.5 out of 5
Dumbarton
Price was $455, price is now $370 per person
$370
per person
Feb 26 - Mar 1
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Richmond (RIC)
This bed & breakfast doesn't skimp on freebies - guests receive free breakfast, free WiFi, and free self parking. Families will appreciate the arcade/game room and barbecue grills. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $669, price is now $545 per person
$545
per person
Feb 26 - Mar 1
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Richmond (RIC)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A snack bar/deli, express check-out, and a computer station are also on offer.

Top Gwynn hotels deals

Gwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water

Gwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water

Grimstead VA
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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!

Gwynn's Island VA
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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
$91 nightly
The price is $101 total per night
$101 total
Dec 15 - Dec 16
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.
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
$95 nightly
The price is $106 total per night
$106 total
Jan 4 - Jan 5, 2026
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
$119 nightly
The price is $135 total per night
$135 total
Dec 10 - Dec 11
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
The Tides Inn

The Tides Inn

4 out of 5
480 King Carter Dr Irvington VA
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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
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See all available properties in Gwynn
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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 $314. 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