Drift into waterfront serenity at this Gwynn's Island vacation rental on the Chesapeake Bay! Mornings start with coffee in the sunroom as the tide rolls in, afternoons melt away on the private beach, and evenings begin with dinner in downtown Mathews, then end with sunset cocktails on the deck. Let this scenic home be your backdrop for a laid-back getaway you’ll want to revisit again and again. Secure your dates today!
-- THE PROPERTY --
OUTDOOR LIVING - Private beach - Deck w/ seating & bay views - Charcoal grill - Yard space
ACCESSIBILITY - Single-story home, 1 exterior step & interior staircase to enter - Acorn stairlift available upon request
PARKING - Driveway (4 vehicles) - Street parking prohibited
-- THE LOCATION --
- 7 miles to Downtown Mathews: Historic Court Square, restaurants, shops, farmers market - 10 miles to Williams Wharf Landing - 13 miles to Zoll Vineyards - 14 miles to Bethel Beach Natural Area Preserve - 17 miles to New Point Comfort Lighthouse - 18 miles to Piankatank River Golf Course - 20 miles to Gloucester, VA - 46-52 miles to Colonial Williamsburg, The Mariners' Museum & Park, Jamestown Settlement
-- REST EASY WITH US --
Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.
-- POLICIES --
- No smoking - Pet friendly w/ $100 fee per stay (+ fees & taxes, dogs only, max 2) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in
ADDITIONAL INFORMATION - This single-story home requires 1 exterior step and an interior staircase to enter. An Acorn stairlift is available upon request
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Gwynn
Located in Gwynn, this holiday home is on the waterfront. Deltaville Marina and Golden Eagle Golf Club are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Chesapeake Bay and Bethel Beach Natural Area Preserve. Deltaville Maritime Museum and Compass Entertainment Complex are also worth visiting.
Busch Gardens Williamsburg - 58 min drive - 84.3 km
Water Country USA - 60 min drive - 85.9 km
Restaurants
Howard-Dooley Cafe - 9 min drive
Seafood Shack - 11 min drive
Hardee's - 12 min drive
Southwind Pizza - 12 min drive
Richardson's Cafe - 12 min drive
Frequently asked questions
Is Gwynn's Island Gem | Private Beach & Bay Views pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Gwynn's Island Gem | Private Beach & Bay Views?
As of 16 October 2026, prices found for a 1-night stay for 2 adults at Gwynn's Island Gem | Private Beach & Bay Views on 25 October 2026 start from NZ$1,613, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Gwynn's Island Gem | Private Beach & Bay Views?
On-site parking is available at the property.
What time is check-in at Gwynn's Island Gem | Private Beach & Bay Views?
Check-in begins at 4:00 PM.
What time is check-out at Gwynn's Island Gem | Private Beach & Bay Views?
Checkout is at 10:00 AM.
Where is Gwynn's Island Gem | Private Beach & Bay Views located?
Situated on the waterfront, this holiday home is within 1 mile (2 km) of Chesapeake Bay and Gwynn's Island Museum. Bethel Beach Natural Area Preserve and Deltaville Maritime Museum are also within 25 miles (40 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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 with family talking and enjoying the solitude. Being on the island is like taking a step back in time, and it truly embodies a traditional coastal community. We loved every minute of our stay and will be back!
We enjoyed our stay. Home was clean with good A/C and the bay breeze also nice outside. My wife really loved the sunrise. The island is a nice quiet get away spot, but still within 10-40 min. or so of some nice small town's or a day trip to York / Williamsburg. Very nice sandy beach, just would have liked access to a small rake for the pine needles. Thank you for a wonderful vacation.
Stayed 7 nights in Jul 2026
Response from VrboOwner on 14 August 2026
We're so glad you enjoyed your stay and that the home's cleanliness and A/C, along with that bay breeze, made for a comfortable visit. It sounds like the sunrise views and the peaceful island setting were a real highlight, while still being close enough to explore small towns or take a day trip to York and Williamsburg. We appreciate you mentioning the beach and the note about the pine needles, that kind of feedback helps us keep improving. Thank you for sharing your experience and for choosing this spot for your getaway.
There was trash left in the trash can in the dining room, which is used as the kitchen trash. I also found trash in a bedroom trash can which smelled bad. Overall the property is lovely with gorgeous views and access to a small private beach. The beach themed decor only added to the property's charm.
Stayed 2 nights in Aug 2026
Verified review
10/10 Excellent
Kieran K.
18 June 2026
Liked: Location
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.