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.
Inn at Blackstone

Inn at Blackstone

2.5 out of 5
Price was $515, price is now $443 per person
$443
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 3 conference rooms, along with the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and wedding services.
Williamsburg Sampler B & B

Williamsburg Sampler B & B

3 out of 5
Price was $615, price is now $493 per person
$493
per person
Apr 20 - Apr 23
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
A restaurant, free self parking, and a coffee shop are among this bed & breakfast's amenities. WiFi in public areas is free. A garden and a library are also provided.
Inn at 605

Inn at 605

3.5 out of 5
West Williamsburg Heights
Price was $593, price is now $482 per person
$482
per person
Apr 20 - Apr 23
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast and free WiFi. Concierge services are provided for your convenience.
The Berkeley Hotel

The Berkeley Hotel

4 out of 5
Downtown Richmond
Price was $706, price is now $576 per person
$576
per person
Apr 30 - May 5
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Country Inn & Suites by Radisson, Ashland - Hanover, VA

Country Inn & Suites by Radisson, Ashland - Hanover, VA

3 out of 5
Price was $639, price is now $537 per person
$537
per person
Apr 30 - May 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
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 24-hour business center and free internet in public areas. There's a gym on site, and a 24-hour front desk and a fireplace in the lobby are also provided.

Top Gwynn hotels deals

Waterfront Cottage on Chesapeake Bay w Private Beach- BOOK YOUR SUMMER '26 WEEK!

Waterfront Cottage on Chesapeake Bay w Private Beach- BOOK YOUR SUMMER '26 WEEK!

Grimstead VA
Get rates
This cottage 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
$87 nightly
The price is $97 total per night
$97 total
Mar 11 - Mar 12
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
Free Cancellation
Reserve now, pay when you stay
$103 nightly
The price is $114 total per night
$114 total
Mar 15 - Mar 16
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
Warner Hall

Warner Hall

3 out of 5
4750 Warner Hall Road Gloucester VA
$223 nightly
The price is $249 total per night
$249 total
Mar 16 - Mar 17
Total with taxes and fees
This inn features free self parking and free WiFi in public areas. Enjoy the free full breakfast each morning.
Cottage on a Private Island in the York River

Cottage on a Private Island in the York River

Gloucester Point VA
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This cottage features a garden, laundry facilities, and barbecue grills.
Experience the Best of Mathews Riverfront Living here at Mariner's Legacy!

Experience the Best of Mathews Riverfront Living here at Mariner's Legacy!

Bohannon VA
Get rates
A gym is featured at this vacation home, along with a garden and laundry facilities. Families will appreciate the playground and barbecue grills.
Kitchen
Washer
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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 $443. 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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