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! (234 reviews)
"The house was perfect, to bad the weather wasn't the first three days we dealt with the nor'easter but it gave us time to rest. Monday night music at the Hole in the Wall was a nice surprise."

Reviewed on Sep 29, 2026

Get rates
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! (5 reviews)
"Excellent experience."

Reviewed on Aug 31, 2026

Get rates
Gwynn's Island Gem | Private Beach & Bay Views
The Tides Inn

The Tides Inn

4 out of 5
480 King Carter Dr Irvington VA
$284 nightly
The price is $306 total per night from Oct 4 to Oct 5
$306 total
Oct 4 - Oct 5
Total with taxes and fees
Book a stay at this beach hotel in Irvington. Enjoy free WiFi, an outdoor pool, and a full-service spa. Popular attractions Steamboat Era Museum and Historic ...
The Tides Inn
See all 364 properties in Gwynn
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! (234 reviews)
"The house was perfect, to bad the weather wasn't the first three days we dealt with the nor'easter but it gave us time to rest. Monday night music at the Hole in the Wall was a nice surprise."

Reviewed on Sep 29, 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! (5 reviews)
"Excellent experience."

Reviewed on Aug 31, 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 Wilkins Beach and Tankards Beach are located ...
9.4/10 Exceptional! (24 reviews)
"Our home was very clean upon arrival, which we appreciated. However, several maintenance, accuracy, and communication issues significantly affected our stay.The front door handle broke off in my hand, and the bathroom towel rack came off the wall when a towel was hung. We repaired both ourselves. ..."

Reviewed on Sep 29, 2026

Smith Beach cottage w/ private sunset
See all properties in Gwynn
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.
See properties

Frequently asked questions

When is the best time to visit Gwynn?
The best time to visit Gwynn is from May through July, during its warmer season, when it is most popular. For fewer crowds and better value, the quieter months of November through January are a good option, offering cooler weather and a more relaxed atmosphere.
What is Gwynn known for?
Gwynn is known for Gwynn's Island Museum, a key institution that offers travelers insights into the local history and culture of the area. This museum provides a focused look at the heritage and unique characteristics of Gwynn.
What is a good itinerary length for Gwynn?
A good itinerary length for Gwynn is a half-day to fully explore Gwynn's Island Museum. For a more leisurely visit, travelers might extend their stay to a full day, allowing ample time to appreciate the museum's exhibits and surroundings.
What are the top things to do in and around Gwynn?
In Gwynn, travelers can visit Gwynn's Island Museum, a local landmark and point of interest.
Can I book a refundable hotel in Gwynn?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Gwynn by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Gwynn with Expedia?
Expedia makes it easier to plan your Gwynn trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Gwynn?
The best choice depends on your travel style. Hotels in Gwynn can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Gwynn trip on Expedia?
Once you've booked your Gwynn trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Gwynn trip?
Expedia offers customer support before, during, and after your Gwynn trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Gwynn?
If it's your first trip to Gwynn, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Gwynn hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Gwynn hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

Explore a world of travel with Expedia