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
Midtown
Price was $650, price is now $435 per person
$435
per person
Nov 7 - Nov 9
found 21 hours ago
Roundtrip non-stop 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.
Wedmore Place

Wedmore Place

3.5 out of 5
Price was $1,009, price is now $692 per person
$692
per person
Oct 23 - Oct 28
found 2 days ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
This boutique hotel features an attached winery, a full-service spa, and a restaurant. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. Enjoy the gym and free perks like continental breakfast and free self parking.
Coles Point Marina

Coles Point Marina

2 out of 5
Save 100% on your flight
Price was $945, price is now $727 per person
$727
per person
Sep 10 - Sep 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Richmond (RIC)
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this cabin. WiFi in public areas is free. A picnic area is also provided.
Kingsmill Resort

Kingsmill Resort

4 out of 5
Kingsmill
Price was $960, price is now $743 per person
$743
per person
Sep 10 - Sep 14
found 2 days ago
Roundtrip flight included
Boston (BOS) 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.
The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
Price was $778, price is now $618 per person
$618
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Gem | Private Beach & Bay Views

Gwynn's Island Gem | Private Beach & Bay Views

Hudgins VA
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This vacation home features barbecue grills.
Kitchen
Washer
Waterfront Cottage w Private Beach on Chesapeake Bay!

Waterfront Cottage w Private Beach on Chesapeake Bay!

Grimstead VA
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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
$96 nightly
The price is $107 total per night
$107 total
Sep 9 - Sep 10
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
The Tides Inn

The Tides Inn

4 out of 5
480 King Carter Dr Irvington VA
$412 nightly
The price is $446 total per night
$446 total
Sep 2 - Sep 3
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.
Quality Inn Kilmarnock

Quality Inn Kilmarnock

2.5 out of 5
599 N Main St Kilmarnock VA
Free Cancellation
$105 nightly
The price is $119 total per night
$119 total
Sep 10 - Sep 11
Total with taxes and fees
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset

Cape Charles VA
$400 nightly
The price is $465 total per night
$465 total
Sep 7 - Sep 8
Total with taxes and fees
This cottage features a gym and a hot tub. Laundry facilities are provided for your convenience.
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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.

Stay near popular Gwynn attractions

Gwynn's Island Museum

10.0/10 (2 reviews)
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.
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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 $435. 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

A pier extending into calm waters at sunset with a clear sky.