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! (238 reviews)
"This charming cottage has a spectacular water view, small private beach and very attractive and comfortable inside furnishings. I was particularly looking for a place we could kayak from easily, and could bring our Golden Retriever Beau, who loves the water.This cottage supplies everything you need ..."

Reviewed on Oct 29, 2026

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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 Deltaville Marina ...
10/10 Exceptional! (6 reviews)
"We ABSOLUTELY loved our stay here. Beautiful views, peaceful, accommodating...it was all of the things. The rooms were spacious, the master bed was nothing short of amazing! So comfortable!The deck needs a little attention, but it certainly served it's purpose, and we enjoyed sitting out at night ..."

Reviewed on Sep 22, 2026

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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
$87 nightly
The price is $97 total per night from Nov 11 to Nov 12
$97 total
Nov 11 - Nov 12
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. ...
Holiday Inn Express Gloucester by IHG
See all 357 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! (238 reviews)
"This charming cottage has a spectacular water view, small private beach and very attractive and comfortable inside furnishings. I was particularly looking for a place we could kayak from easily, and could bring our Golden Retriever Beau, who loves the water.This cottage supplies everything you need ..."

Reviewed on Oct 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 Deltaville Marina ...
10/10 Exceptional! (6 reviews)
"We ABSOLUTELY loved our stay here. Beautiful views, peaceful, accommodating...it was all of the things. The rooms were spacious, the master bed was nothing short of amazing! So comfortable!The deck needs a little attention, but it certainly served it's purpose, and we enjoyed sitting out at night ..."

Reviewed on Sep 22, 2026

Gwynn's Island Gem | Private Beach & Bay Views
Cottage on a Private Island in the York River

Cottage on a Private Island in the York River

Gloucester Point VA
Book a stay at this family-friendly cottage in Hayes. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Carmines Islands and Tyler Island ...
9.8/10 Exceptional! (388 reviews)
"We had a lovely time on the private island- a unique and beautiful place. Enjoyed sunset on one porch and sunrise on another. And very convenient to historical sites, great dining, and fun activities. Hope to return someday."

Reviewed on Oct 31, 2026

Cottage on a Private Island in the York River
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.
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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.

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