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Waterfront Cottage w Private Beach on Chesapeake Bay!

Photo gallery for Waterfront Cottage w Private Beach on Chesapeake Bay!

A wooden deck leading to a body of water with a clear sky.
Property video
A wooden dining table with six chairs, each with a colorful striped cushion. The table is set with a green placemat and a small stack of plates.
A single-story house with a wooden deck and stairs leading to a front door.
A room with a view of a body of water, a table with a lamp, and a chair.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Bring your furry friends
    Top-rated for creating memorable stays with your pets.
  • Direct access to the beach
    A rare find — enjoy uninterrupted access to the beach.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Gwynn's Island Museum

Popular amenities

  • Direct access to private beach
  • Patio
  • Toys
  • Internet access
  • Barbecue grill
  • Pet-friendly

Explore the area

View in a map
Grimstead, VA
  • Place, Gwynn's Island Museum
    ‪15 min walk‬
  • Place, Deltaville Marina
    ‪26 min drive‬
  • Place, Busch Gardens Williamsburg
    ‪54 min drive‬
  • Airport, Newport News, VA (PHF-Newport News - Williamsburg Intl.)
    ‪59 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

2 Twin Beds

1 bathroom

Bathroom 1

Bathtub or shower · Toilet

Spaces

Deck or patio
Kitchen
Garden
Dining area

Add dates for prices

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9.8 out of 10, Exceptional, (65 reviews)
Cozy cottage on the Chesapeake Bay

About the neighborhood

Gwynn

Located in Gwynn, this cottage is in a rural area and on the beach. The area's natural beauty can be seen at Chesapeake Bay and Bethel Beach Natural Area Preserve, while Gloucester Museum of History and Deltaville Maritime Museum are cultural highlights. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with hiking/biking trails and hunting.
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Map
Grimstead, VA

What's nearby

  • Gwynn's Island Museum - 15 min walk - 1.3 km
  • Chesapeake Bay - 3 min drive - 2.4 km
  • Deltaville Marina - 26 min drive - 39.9 km
  • Busch Gardens Williamsburg - 54 min drive - 80.6 km
  • Langley Air Force Base - 60 min drive - 91.8 km

Getting around

  • Newport News - Williamsburg Intl. Airport (PHF) - 55 min drive

Restaurants

  • ‪Howard-Dooley Cafe - ‬6 min drive
  • ‪Seafood Shack - ‬7 min drive
  • ‪Hardee's - ‬8 min drive
  • ‪Southwind Pizza - ‬9 min drive
  • ‪Richardson's Cafe - ‬9 min drive

Frequently asked questions

Is Waterfront Cottage w Private Beach on Chesapeake Bay! pet-friendly?

Yes, this property allows cats and dogs (limit 2 total) with a maximum weight of up to 50 lbs per pet.

How much does it cost to stay at Waterfront Cottage w Private Beach on Chesapeake Bay!?

As of Oct 29, 2026, prices found for a 1-night stay for 2 adults at Waterfront Cottage w Private Beach on Chesapeake Bay! on Nov 2, 2026 start from $355, 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?

Onsite parking is available at the property.

What time is check-in at Waterfront Cottage w Private Beach on Chesapeake Bay!?

Check-in begins at 3:00 PM.

What time is check-out at Waterfront Cottage w Private Beach on Chesapeake Bay!?

Check-out is at 11:00 AM.

Where is Waterfront Cottage w Private Beach on Chesapeake Bay! located?

Nestled on the beach, this Gwynn cottage is 0.8 mi (1.2 km) from Gwynn's Island Museum and 1.7 mi (2.7 km) from Chesapeake Bay. Bethel Beach Natural Area Preserve is 11.9 mi (19.2 km) away.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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Rating 10 - Excellent. 228 out of 237 reviews
Rating 8 - Good. 7 out of 237 reviews
Rating 6 - Okay. 2 out of 237 reviews
Rating 4 - Poor. 0 out of 237 reviews
Rating 2 - Terrible. 0 out of 237 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Cute cottage with great views! Very relaxing getaway.
Stayed 4 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place and the dogs loved the beach
Stayed 7 nights in Aug 2026
Response from VrboOwner on Aug 30, 2026
Thanks a ton Harry! We so appreciate your review. Please bring the pups back any time.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely cottage, beautifully decorated, clean, gorgeous views, appointed with anything you could think you might need. Just a wonderful getaway.
Stayed 3 nights in Sep 2026
Response from VrboOwner on Sep 24, 2026
Thank you Susan! Such a great photo of the large blue heron who hangs out on the bulkhead right in front of the Cottage! We appreciate your kind review and welcome you back to the Cottage any time.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The cottage is truly a magical place, especially for those with a water-loving dog that also loves to roll or lay in the grass! We’ve been here multiple times, and as always, the cottage was in great shape and the host was so communicative and responsive—before, during, and after our stays. We always think about when we can return again after each of our stays. It’s truly a cozy and comfortable home away from home with magnificent views of the bay/river. Don’t miss the sunsets from the cottage!
Stayed 5 nights in Oct 2026
Response from VrboOwner on Oct 22, 2026
Thank you, Ji! And for being such a thoughtful guest when the weather and a power outage didn't provide an optimal stay for you. We look forward to having you back for a calmer weather visit!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed a very relaxing weekend. Luckily, it was a warm one, and my granddaughter was able to swim in October, which was pretty cool. Host very accommodating. Love the little island. Drove all around the Island and enjoyed the views from different areas.Ate at the hole in the wall for dinner and found it to be good. Seemed to be a real Saturday night hangout spot with many people eating dinner and enjoying the beautiful evening.
Stayed 2 nights in Oct 2026
Response from VrboOwner on Oct 14, 2026
Oh thank you Janice! So glad for your family time at the Cottage! And thanks for your patience with interruptions and identifying conditions for us. We greatly appreciate it and welcome you back any time.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 4 nights in Sep 2026
Response from VrboOwner on Sep 29, 2026
I am so glad you found the Cottage enjoyable. The only thing we have no control over is the weather, so I am so sorry that impacted your stay. Please come back to the Cottage any time and thanks much for your review! We appreciate it.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was our fifth stay here and it somehow keeps getting better! The Cottage has everything you could ever want for a vacation, including amazing restaurants close by. The beautiful sunsets every night, the private beach with clear Hills Bay water, the peacefulness — and we get to enjoy it all with our dogs! Cheri could not be a better host and always goes above and beyond. We are so grateful that she shares her little piece of heaven!!
Stayed 7 nights in Aug 2026
Response from VrboOwner on Aug 31, 2026
Thank you so much for your review! Very kind of you guys. You are most welcome back any time.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Stayed 7 nights in Jul 2026
Response from VrboOwner on Jul 26, 2026
Thanks for your gracious review, Joyce and Gary! And for all of your communications. I appreciate it so much! Please come back to the cottage soon.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful rental property. Gorgeous views of the bay! Kitchen is well-equipped with everything you need. Area is peaceful and quiet. We loved the private beach area and the mornings were shady. Would stay here again!
Stayed 7 nights in Jul 2026
Response from VrboOwner on Jul 12, 2026
Sharon! Thank you much for your generous review. And thanks for your keen observations at the Cottage. We hope to have you back soon.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We truly cannot say enough wonderful things about this home and our host! This has become our absolute favorite place to stay, and there’s a reason we continue coming back. The home is beautiful, comfortable, incredibly well cared for, and always feels like such a special place to get away.Our host goes above and beyond to make every stay feel welcoming and thoughtful. You can genuinely tell how much care she puts into the home and into making sure her guests have a wonderful experience. It’s those little extra touches and attention to detail that make staying here feel so different from anywhere else we’ve stayed.The cottage has become such a special place for us, and we look forward to coming back every time. We always leave wishing we could stay longer! We’re so grateful to have found this little getaway and couldn’t recommend the home or our host more highly.
Stayed 3 nights in Sep 2026
Response from VrboOwner on Sep 22, 2026
I can't thank you enough for your frequent bookings of the Cottage, always taking care of it, and your very kind reviews. When VRBO is threatening to take away my premier host status because of one less than 10 star review in the last 6 years, reviews like yours mean a lot and even more. See you back at the Cottage soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had another excellent stay at Gwynn's Island cottage. We had wonderful views of Hills bay and great weather to go along with it. The cottage was clean and well stocked as always. Thanks again Cheri for letting us stay at this gem in Mathews County, Virginia and for being a wonderful hostess.
Stayed 7 nights in May 2026
Response from VrboOwner on Jun 23, 2026
Thanks so much to your family for being great repeat guests! Appreciate the review!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This quiet, water-front cottage was perfect for my husband and me. We hope we can stay here again.
Stayed 4 nights in Apr 2026
Response from VrboOwner on Apr 27, 2026
Thank you so very much for your review of your stay! And for your comments on me on the clean condition of the Cottage. We appreciate your kind comments so much and hope to have you both soon.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a lovely weekend stay at this inviting cozy cottage. The kitchen was very well stocked with everything we needed. We enjoyed relaxing on the deck and enjoying the views. The beach was perfect for wading and given more time I would have gone swimming. My husband enjoyed kayaking in the surrounding waters. The quiet island atmosphere was just what we wanted and we will return.
Stayed 2 nights in May 2026
Response from VrboOwner on May 19, 2026
Beth! Thanks much for your review! You really took full advantage of the cottage. You are welcome back for next year's Tour or at any time.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a fabulous time at the cottage! It had everything you could possibly want to make your stay enjoyable and entertaining. We were there to rest & recuperate after some recent medical issues, so we didn't use any of the water/recreational equipment but it was available (hubby looked in the shed). Believe the extensive amenities listing -- Cheri was very accurate in listing what was provided and available for use.The photos posted of the cottage were also very accurate but they didn't convey how clean the cottage was (no inside bugs, even) and especially, the magnificent view. We were mesmerized by the view! Sitting in the great room, looking out of the windows, all we could see was water and sky. We felt like we were on a houseboat!At first, I didn't think I'd like being on the river side of Gwynn's instead of on the Bay side. Turns out, it was a plus. We didn't want to cook so it was really easy to get to the 2 island restaurants and to all the Mathews' restaurants.I also appreciated Cheri's helpfulness, hospitality and availability. I really enjoyed communicating with her. She made everything so easy for us and we'd love to return to the cottage again.
Stayed 7 nights in Aug 2026
Response from VrboOwner on Sep 14, 2026
Thanks so much for this kind review!! I'm so glad you found the cottage in good condition! We appreciate your taking the time to review your stay and you are welcome to come back when you can dig into the shed items!
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a lovely time.
Stayed 2 nights in Nov 2025
Response from VrboOwner on Dec 4, 2025
Hi Carolyn - Thanks for your review and glad you enjoyed a stay after the holiday. I don't believe we got any communications from you before, during or after your stay, so I know of no concerns with your stay. We are disappointed in your 4 star review as there is no indication from your review what was lacking. (We haven't had anything but 5 star reviews for almost 8 years of renting.) If you wish to message me and share your experience with us and what was lacking, we would be happy to hear about it. We always look for ways to improve guests' experience. A complaint can be a gift. Thanks much!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet Beach Getaway

We had a great time staying here. The private beach was exactly what we needed to relax and have fun.
Stayed 2 nights in May 2025
Response from VrboOwner on Jun 3, 2025
Thanks Christen! You guys were ideal guests. We hope to have you back at the Cottage soon.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great views and location

3 night visit - location close to relative and convenient to Mathew’s Va and Williamsburg Va
Stayed 3 nights in Apr 2025
Response from VrboOwner on Apr 16, 2025
Thank you, Robert! And thanks to you and your family for being return guests at the Cottage.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very relaxing vacation with beautiful view. Very clean and well stocked with everything needed.
Stayed 7 nights in Aug 2025
Response from VrboOwner on Aug 19, 2025
Thanks, Ed! And for being such kind guests. Glad you had a good stay and hope you will consider returning.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Stay

Terrific stay, the best communication, lots of fun amenities, specatacular sunsets and everything you need , right at your finger tips.
Stayed 7 nights in Aug 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We have stayed at Gwynn’s Island Cottage four times now and each visit only gets better. Cheri is the most thoughtful and welcoming host — you feel right at home as soon as you walk in. The Cottage has always been immaculate and has everything you could ever think to need during your stay. The views, the water, the private beach.. it’s almost surreal. We bring our dog who enjoys the beach and water as much as we do. The sunsets every night are breathtaking. With great restaurants on the island and nearby in Mathews, it’s hard to imagine a more perfect location for a getaway. We are so thankful Cheri shares her little slice of heaven and are already looking forward to our next visit!!
Stayed 7 nights in Apr 2026
Response from VrboOwner on Apr 12, 2026
Thanks so much! We appreciate your review so much! You guys are such terrific guests. Please come back soon!!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely getaway

My daughter's and I had a wonderful stay at the cottage! It has everything you need andwithin 30/40 min drive from various little towns and beaches.
Stayed 8 nights in Mar 2025
Response from VrboOwner on Apr 9, 2025
Thanks so much Elizabeth! And for being a terrific guest. Ya'll are welcome back to the Cottage for your spring break any time.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our stay is always so good for us. Our dog loves the easy in and out and all amenities are well thought out. We love seeing the eagles, herons, and osprey. We don’t fish but lots were jumping around ight out front.
Stayed 11 nights in Sep 2025
Response from VrboOwner on Oct 17, 2025
Thanks so much, Janis! You guys are such terrific repeat guests that it's a pleasure to host you. We look forward to having you back after the renovations!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great vacation spot

Excellent place to kick back and relax. Very pleased with everything and will be back
Stayed 7 nights in Jul 2022
Response from VrboOwner on Jul 28, 2022
We appreciated having you as great guests. Please come back any time, Ryan!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family vacation

We love the private beach and the wonderful sunsets! Great location to get away from it all.
Stayed 7 nights in Aug 2019
Response from VrboOwner on Mar 23, 2020
Margaret - I am so grateful that your family chooses to come back to the Cottage for your summer vacation each year. Many thanks.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend getaway

It was a perfect spot for an intimate weekend getaway. The pups absolutely loved it, and Beaverdam park is close enough that we were able to get a nice long hoke in as well.
Stayed 2 nights in Oct 2024
Response from VrboOwner on Oct 6, 2024
Thanks so much Amy! And you have introduced me to Beaverdam where I have not yet been so I am grateful! Please come back with your pups!
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