Gwynn, VA

Travel Guide

A pier extending into calm waters at sunset with a clear sky.
Waterfront Cottage w Private Beach on Chesapeake Bay!

Waterfront Cottage w Private Beach on Chesapeake Bay!

Grimstead VA
Book a stay at this beach cottage in Gwynn. Enjoy free WiFi, a beach locale, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...
10/10 Exceptional! (228 reviews)
"The Cottage at Gwynn Island is truly magical. Such a wonderful setting on the bay with a private beach to swim with our doggies.Our host was extremely kind and we look forward to visiting again soonSincerely Joyce and Gary"

Reviewed on Jul 26, 2026

Waterfront Cottage w Private Beach on Chesapeake Bay!
Gwynn's Island Gem | Private Beach & Bay Views

Gwynn's Island Gem | Private Beach & Bay Views

Hudgins VA
Stay at this vacation home in Gwynn. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Gwynn's Island Museum and Holly Point Nature ...
10/10 Exceptional! (2 reviews)
"Excellent location with sandy private beach on West side of Chesapeake Bay. Shallow water and no undertow made for safe and fun time for children in group. Loved the daily appearance of Bald Eagles in the nearby pines. Definitely hope to return."

Reviewed on Jun 18, 2026

Gwynn's Island Gem | Private Beach & Bay Views
Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG

3.5 out of 5
6639 Forest Hill Ave Gloucester VA
$100 nightly
The price is $111 total per night from Sep 3 to Sep 4
$111 total
Sep 3 - Sep 4
Total with taxes and fees
Book a stay at this business-friendly hotel in Gloucester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7.2/10 Good! (724 reviews)
"Nice breakfast variety"

Reviewed on Aug 4, 2026

Holiday Inn Express Gloucester by IHG
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.
Waterfront Cottage w Private Beach on Chesapeake Bay!

Waterfront Cottage w Private Beach on Chesapeake Bay!

Grimstead VA
Book a stay at this beach cottage in Gwynn. Enjoy free WiFi, a beach locale, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...
10/10 Exceptional! (228 reviews)
"The Cottage at Gwynn Island is truly magical. Such a wonderful setting on the bay with a private beach to swim with our doggies.Our host was extremely kind and we look forward to visiting again soonSincerely Joyce and Gary"

Reviewed on Jul 26, 2026

Waterfront Cottage w Private Beach on Chesapeake Bay!
Gwynn's Island Gem | Private Beach & Bay Views

Gwynn's Island Gem | Private Beach & Bay Views

Hudgins VA
Stay at this vacation home in Gwynn. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Gwynn's Island Museum and Holly Point Nature ...
10/10 Exceptional! (2 reviews)
"Excellent location with sandy private beach on West side of Chesapeake Bay. Shallow water and no undertow made for safe and fun time for children in group. Loved the daily appearance of Bald Eagles in the nearby pines. Definitely hope to return."

Reviewed on Jun 18, 2026

Gwynn's Island Gem | Private Beach & Bay Views
Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset

Cape Charles VA
Stay at this cottage in Eastville. Enjoy a fitness center, laundry facilities, and patios. Popular attractions Cape Charles Beach and Wilkins Beach are located ...
Smith Beach cottage w/ private sunset
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

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