Entire home

Gwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water

Beachfront cottage with kitchen and patio

Photo gallery for Gwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water

Property grounds
On the beach, sun-loungers, beach towels
Smart TV, DVD player, books, video library
Smart TV, DVD player, books, video library
Exterior
Experience the tranquility of Gwynn's Island Cottage, a waterfront haven with panoramic views and sunsets over the water. Enjoy a private beach for swimming, kayaking, paddle boarding, fishing and crabbing – all steps away from your cozy 2-bedroom retreat that sleeps 4 guests. You can unwind in an outdoor shower after your day on the beach or savor local seafood at our Weber kettle charcoal grill.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms1 bathroomSleeps 41200 sq ft

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Kitchen

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Gwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water

Gwynn's Island Cottage is a waterfront cottage on the Chesapeake Bay with panoramic views and sunsets over the water. The small, private beach - entirely on the property and not shared - is mere steps away. We are pet friendly. The Cottage is located on quaint and historic Gwynn's Island with a public marina and restaurant 1/3 of a mile away on the island. The Cottage sleeps 4 guests in 2 bedrooms.

From the private beach, guests can swim, kayak, paddle board, fish and crab, bird watch, float on a raft, lounge or just enjoy a good book or an adult beverage. The Shed is full of everything you don't need to bring: beach chairs, zero gravity chairs, 3 kayaks, a stand up paddleboard, crab nets, crab pot, floats, rafts, noodles, children's beach toys, life vests, a croquet set, and hammock. Hills Bay is clean, shallow, and sandy-bottomed, with little current or tow, so perfect for children and explorers alike. Guests can fish right from the beach or from kayaks and can catch drum, trout, rockfish, croaker, spot and flounder. The crab pot or the fishing nets allow guests to catch crabs when they are in season.

After a quick rinse in the outdoor shower after your day on the beach and on the water, use the Weber kettle charcoal grill for cooking up the day’s catch or fresh seafood from a nearby market. Enjoy dinner al fresco on the deck overlooking the water as you watch that sunset... For cooler evenings, light a fire in the Bonfire Solo stove under the stars.

From the Cottage, guests experience bird life such as bald eagles nesting, blue herons, osprey, seagulls, white tundra swans, bufflehead ducks, loons, and dolphins, depending on the season. With a yacht club just across the water, you can watch all kinds of sail and motor boats coming in and out of Hills Bay from the Chesapeake as well as occasional boat races.

Or bring your own boat. There's plenty of room on the long, circular driveway to trailer in and out. The island's public boat landing is 1/3 of a mile away, with parking for your trailer while you are on the water and a restaurant for provisions.

The Cottage is pet-friendly! Four legged guests enjoy the beach with its shallow, clean water. We provide doggie towels. We own the small woods next door where dogs can "get their sniffs on."

If you plan to bring your pet, please message the manager with the age, breed, gender, weight, and name of your animal/s. We charge a pet fee of $125 for all animals for your entire stay (less than kennels or pet sitters). They will enjoy being with you on vacay.

Between Memorial Day weekend and Labor Day weekend, we rent by the week, Sunday to Sunday (less traffic on interstates than Saturdays). A two-night minimum the rest of the year.

We have a large capacity washer, dryer, and the laundry room has space to air dry. Our outdoor shower also has foot spigots. The Cottage has a smart TV with cable and wifi. If you bring your electric or hybrid vehicle, we have an electrical outlet (120v) on the front of the Cottage for charging.

The Cottage has a retro Frigidaire Mini-fridge that chills 6 cans of your favorite beverage and doubles as a Bluetooth speaker. Take it outside to play your tunes on the beach or deck.

The Cottage is perfect for special occasions or gatherings (with approval of management) because photos with a water view are ah-mazing.

Please read the over 200 reviews from the Cottage's guests, many of whom return over and over again. Our positive reviews reflect the guest-centered experience that we try to provide, continually using our guests' suggestions to improve amenities.

We are sorry but smoking is not permitted in the house or anywhere on our property.

Gwynn's Island Cottage is dedicated to welcoming all people regardless of their race, color, religion, ethnicity, national origin or gender orientation.

Property amenities

Beach

  • Direct access to a private beach
  • Beach loungers
  • Beach towels

Internet

  • Available in the cottage: Free WiFi

Parking and transport

  • Car recommended
  • Onsite parking options include a garage

Kitchen

  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Hob
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Books
  • DVD player
  • Games
  • Smart TV with cable/satellite channels
  • Stereo
  • Video library

Outdoor areas

  • Charcoal grill
  • Garden
  • Outdoor furniture
  • Patio
  • Yard

Laundry

  • Laundry facilities
  • Washer/dryer

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming cats and dogs only
  • Up to 23 kg per pet

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • No lift (single-level property)
  • Thin carpet in public areas
  • Tile flooring in public areas
  • Wheelchair-accessible path of travel
  • Smoke-free property

Services and conveniences

  • Housekeeping (limited availability)
  • Iron/ironing board

Location highlights

  • In a rural location
  • In a village
  • Near a health/beauty spa
  • Near a hospital
  • Near the bay
  • Near the marina
  • On a river
  • On the waterfront

Things to do

  • Bicycles
  • Golf
  • Kayak
  • Water sports equipment
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Hunting nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Rafting nearby
  • Sailing nearby
  • Snorkelling nearby
  • Swimming nearby
  • Water skiing nearby
  • Wildlife walks nearby
  • Windsurfing nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Bicycles
  • Garden
  • Unit size: 1,200 square feet

Similar properties

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age - 22

Check-out

Check-out before 11:00 AM
Contactless check-out

Special check-in instructions

Guests will receive lockbox information
You will receive an email from the host with check-in and check-out instructions

Check-out instructions

The host requires you to complete the following before checking out:
Load and start the dishwasher
Strip any used beds and gather used towels
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights, lock the doors and return the keys
We ask that guests launder any sheets or towels that were used during your stay (if you did not bring your own). If you don't finish a load, no problem, just let us know.
Text Cheri the manager when you check out. 434-962-0726.
In the keypad on the front door, please press SCHLAGE button, then the code, then turn thumb lock to the LEFT to engage the lock. Thanks!
Failure to complete these may result in a negative review from the host.

Access methods

Lockbox

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs and cats only
2 total (up to 23 kg per pet)
Restrictions apply; for more information contact the property on the number on the booking confirmation
Note from host: With advance ok of management and pet fee of $125

Children and extra beds

Children are welcome
Note from host: Small beach and shallow water are great for kids

Events

Events allowed: family gatherings, birthday parties, weddings
Special events and parties with okay of management

Smoking

Smoking is not permitted

Important information

You need to know

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
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 30
Note from host: Special events and parties with okay of management
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, a first aid kit and a deadlock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

A car is recommended for transport to and from this property

Property is also known as

Gwynn's Island Cottage November Dates Open!
GWYNN'S ISLAND COTTAGE Book Your November December Dates!
GWYNN'S ISLAND COTTAGE Come Experience the Chesapeake Bay!
Gwynn's Island Cottage on the Bay OCTOBER DATES AVAILABLE!
GWYNN'S ISLAND COTTAGE ON THE BAY Book Your Fall Stay Now!
GWYNN'S ISLAND COTTAGE Second Weekend in May Now Available!
Gwynn's Island Cottage ON THE BAY Book Your Summer Stay Now!
Gwynn's Island Cottage Book Your November December Dates Now!
GWYNN'S ISLAND COTTAGE ON THE BAY October dates still available!

About the area

Map
Grimstead, VA

What's nearby

  • Gwynn's Island Musuem - 15 min walk - 1.3 km
  • Chesapeake Bay - 4 min drive - 2.7 km
  • Deltaville Marina - 33 min drive - 38.5 km
  • Deltaville Maritime Museum - 33 min drive - 38.9 km
  • Holly Point Nature Park - 33 min drive - 38.9 km

Getting around

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

Restaurants

  • ‪Hole In The Wall - ‬13 min walk
  • ‪Howard-Dooley Cafe - ‬6 min drive
  • ‪The Hatchery Culture - ‬9 min walk
  • ‪The Table at Wilton - ‬25 min drive
  • ‪Mi Casa Azteca Mexican Restaurant & Cantina - ‬9 min drive

Frequently asked questions

Is Gwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water pet-friendly?

Yes, this property allows cats and dogs (limit 2 total) with a maximum weight of up to 23 kg per pet. Some restrictions may apply, so please contact the property for more details.

What time is check-in at Gwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water?

Check-in begins at 3:00 PM.

What time is check-out at Gwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water?

Checkout is at 11:00 AM.

Where is Gwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water located?

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

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Reviews

Gwynn's Island Cottage - Waterfront with Private Beach + Sunsets over Water Reviews

10

Exceptional

10

Cleanliness

9.8

Location
Rating 10 - Excellent. 211 out of 219 reviews
Rating 8 - Good. 6 out of 219 reviews
Rating 6 - Okay. 2 out of 219 reviews
Rating 4 - Poor. 0 out of 219 reviews
Rating 2 - Terrible. 0 out of 219 reviews

Reviews

10/10 Excellent

Amy E.

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

Girl Weekend Getaway

We had the perfect weekend here at the Waterfront Cottage! We’ll definitely return!
Stayed 2 nights in Mar 2025

10/10 Excellent

Kris K.

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

Amazing Views

Everything you need is here, crab pots-caught a few blue crabs. Went fishing, we caught skate, croaker and an eel. 3 Kayaks, beach chairs, SUP , well stockedgrill, etc.
Stayed 3 nights in May 2025

10/10 Excellent

Mike M.

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

10/10 Excellent

Haley C.

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

Another amazing trip in the books at our favorite place

This is our dream place. Every single time we stay we never want to leave. It is like a 2nd home to us. The most wonderful vibes and views, you couldn’t ask for more. Cheri is an AMAZING host. She is the absolute best and makes sure we are all set for a fabulous stay every time!!! We can’t wait to come back!
Stayed 3 nights in Nov 2024

10/10 Excellent

frank c.

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

Great Waterfront Cottage

The house is very nice, and the little private beach is awesome, sandy beach, calm water, and incredible view!
Stayed 4 nights in Apr 2021

10/10 Excellent

Garnette B.

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

Amazing veiw

Extremely clean, very accommodating..So peaceful..Young families or retired you will love staying here.. Great for young children..no jelly fish to worry about...and shallower waters for them to enjoy the beach area.
Stayed 14 nights in Sep 2019

10/10 Excellent

Beverly S.

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

Right on the water

The cottage was a prefect size for two guests and lots of room outside. Was truly as advertised! Enjoyed watching terns and osprey fish close by. Nicely furnished and equipped and well kept. Will definitely consider going again.
Stayed 4 nights in Sep 2024

10/10 Excellent

Katie L.

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

Perfect Getaway

This is a cozy gem on the water. We loved every minute of it. Hope to return soon!
Stayed 3 nights in Apr 2022

10/10 Excellent

Haley C.

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

A Perfect Getaway

This has become our getaway place! My husband and I love this place and so does our 2 year old sheepadoodle Walter! It’s the best time, every single time. Cheri is amazing to work with and always ensures a smooth check in and a beautiful clean home with the best vibes. We will continue to come back every year!
Stayed 3 nights in Sep 2024

10/10 Excellent

DeAnna D.

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

Great Time on Gwynn's Island

We had an awesome family weekend get away. Property is as advertised! It was clean and the views were amazing! We had dinner at Hole In The Wall. The food was great and there was live music. Definitely on our to do again list!
Stayed 2 nights in Nov 2019

10/10 Excellent

Ashley S.

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

Amazing Sunsets

This property was everything I needed to relax and recharge before starting a new year! Amazing views and sunsets every day. Cheri gave helpful information prior to check in and made sure we had everything we needed. Highly recommend!
Stayed 3 nights in Dec 2022

10/10 Excellent

Ji B., Alexandria, VA

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

Still a slice of heaven on earth

This is our 3rd time staying at this property and the owner is always so easy to communicate with. The property is clean and cozy. We especially enjoy the views. The view of the water and the sunsets are amazing and our dog particularly loves the beach access. His own private beach for a few days.
Stayed 3 nights in Oct 2022

10/10 Excellent

Rose H., manchester

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

Above & Beyond Expectations !!!!

Very Very clean and well stocked with amenities.. The view was just beautify and very relaxing. This cottage is five stars plus all the way around. We had a wonderful time and look forward to visiting again. Rose Hudgins
Stayed 6 nights in Sep 2021

10/10 Excellent

Dennis E.

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

Amazing experience

This property was as described and more. The Property Manager was very prompt and helpful. The property was very well equipped with everything that we needed and was very clean. The area was beautiful, very quiet and peaceful. This definitely a great experience..
Stayed 7 nights in May 2021

10/10 Excellent

Amy W.

Cozy and fantastic view!

My husband and I spent Thanksgiving 2018 at the cottage. It is right on the water, you can see the water from the couch! Everything was super clean and organized. It was quiet and serene and a much-needed break from work and the city! I highly recommend the cottage.
Stayed 4 nights in Nov 2018

10/10 Excellent

Susan M., Chester Va

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

In-joyed!

I in-joyed myself there with such beautiful views and easy access to the water. Went kayaking sailing! Rode my bike all over the island. It's a very relaxing vacation home, clean, and well stocked. I wished I had booked a longer stay!
Stayed 4 nights in Sep 2022

10/10 Excellent

Bob M.

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

My stay at gwynns island cottage.Great vacation!!

I loved evert minute of it . Aet at Hole In The Wall, Had the best crab cakes ever. I also at at the mexican restaurant in Mathews courthouse. great food and staff. visited with my son and family. Went fishing with him and to the gun range in White Stone. Everything was great!!! Can, wait to go back. Bob Moore from Columbia, SC
Stayed 7 nights in Oct 2021

10/10 Excellent

Chris L.

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

What a beautiful paradise!

My family and I absolutely loved this property. Almost everything needed was provided and if we needed something, Food Lion is really close! The cottage was clean and very beautiful. The private beach was amazing as well. Our 2 and 4 year olds absolutely loved playing in the water and making sand castles. There's lots of nature to see including Ospreys, Bald Eagles, Blue Herons, crabs and many different gulls. We also got to see dolphins one morning!!! The beds were comfortable and the furniture was nice as well. We really hope to make it back in years to come!!! Thanks for everything Cheri! Communication was fantastic!!
Stayed 7 nights in Aug 2021

10/10 Excellent

Kim H.

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

Fantastic!

If you crave a peaceful and relaxing getaway, this is the place for you! This quaint cottage is cozy, comfortable and unpretentious. It was clean and stocked with essentially everything you might need or want. The bay is your backyard and I could’ve easily spent all day relaxing on the patio, taking in the heavenly view (especially the sunset!) and listening to the soothing sounds of the water and jumping fish. My husband and son enjoyed fishing from the double kayak everyday and caught several red drums and bluefish. We had fun catching crabs, watching the cormorants dive for lunch and even saw a school of dolphins. A majestic heron visited the jetty for several minutes every night after dark. Cheri was exceptionally responsive and kind, offering a ton of helpful info. We hated to see our time at Gwynn’s Island Cottage end, and would love to visit again! Thank you so much Cheri, for sharing your little slice of heaven with us!
Stayed 4 nights in Sep 2024
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Curtis & Deborah H.

All the comforts of home, Very Nice!

We certainly appreciate your beautiful comfortable cottage having everything needed and more for a fabulous stay on Gwynn's Island! We tried out many of the local restaurants in Mathews and we're impressed with them all. No bad experiences anywhere during our stay and we hope to be able to come back someday! We highly recommend this cottage to a couple needing a getaway like us, or to a small family. Lots of shade in the marvelous back yard which is right on the water, perfect for relaxing anytime, night or day. Furnished with numerous amenities, friendly neighbors and neighborhood. We enjoyed a couple walks to the little Hill Bay store and deli a couple doors away (they even have LIVE BAIT). The owner Cheri is very quick to respond to inquiries before or after arrival. Thanks so much, C & D Hartless
Stayed 3 nights in Sep 2017

10/10 Excellent

Karen P.

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

Want to give 12 stars but limited to 5 stars

The Gwynn Island Cottage hosted by Cheri is everything my friends and family wanted in a week by the beach. As “Golden Girls,” we were looking for rest, relaxation, food, wine and spirits, sharing, crabbing and fishing. Cheri has made sure that VRBO guests will be well informed where things are: every switch, cabinet and shelf was labeled -so easy navigation as if the home was yours. Cheri, the host, has not only been attentive to guests needs, but the decor and landscaping was meticulous and beach-y. The cottage was immaculate and well-stocked; however, the host mentions that not all toiletries are provided. But there is much provided in the kitchen and bathroom. We brought extra septic-safe toilet paoer, paper towels, Clorox wipes, etc. I would probably bring liquid hand soap, next time. We took advantage of the Weber Grill. We bought an extra small bag of original kingsford charcoal briquettes, but the was a bag there of Kingsford match-light. We didn’t use much, so the next guest will have both. I strongly suggest you read the cottage “Bible” book that Cheri put together to know the cottage rules, but also her tips and insights into the island history and resources. She has some spot on suggestions on activities and restaurants. Cheri appears conscientious and was responsive to our needs, so communication is one of her fortes. We all agree that Cheri and her cottage will delight! Enjoy!
Stayed 7 nights in May 2025
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Meg P.

Wonderful, fantastic getaway at a delightful cottage!

My review is a bit overdue, but I still find it necessary to write and thank the owner for a truly lovely and fabulous week at her cottage. First, she is very accommodating and immediately responds to any calls regarding questions or possible concerns. Secondly, this was our 4th visit to this great cottage over the course of the last 5 years. We had stayed there prior to the current owner purchasing the property, and although very nice, it was in need of some small updates. The owner resolved those needs immediately upon purchase and has made a stay there one of our favorite little getaways! The location is not only spectacularly beautiful, but the cottage is quite comfortable and allows for a nice, relaxing stay. If you're looking for a quiet and relaxing place to stay, this is it. However, don't be fooled by the pleasant ambiance! There is a lot to do in the area (all within one hour of the cabin) and several nice restaurants in Mathews. We look forward to our next visit!

10/10 Excellent

Bekky M.

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

Wonderful Bay Retreat at Grimstead

We first chose this cottage on Hill’s Bay for a trip in 2022 because of its solitude and private beach, in addition we could bring our dogs, which was a top priority for us. Because of how wonderfully that trip went, we booked our second visit in April, 2023 and could not have been more pleased. The host, Cheri, pays so much attention to detail, a stay in her charming cottage is restful, invigorating, and fun, no matter what the weather. Besides a beautifully decorated and outfitted living environment, the view of the bay provides a never-ending waterscape to observe. Cheri stocks the cottage with books, games, internet access and more, if you choose to stay inside. Outside, a shed full of water equipment provides recreational opportunities on the bay. We tried out the kayaks and paddleboard with our pups and had so much fun! Communications with Cheri were excellent and I was amazed with how easy check in and out went. A small parcel of woods at one side of the cottage provided us with nature-viewing opportunities and a place to walk the dogs. We loved every minute of our stay, from the cottage life to visits to local beaches such as Aaron and Haven Beaches. Local restaurants in the town of Matthew’s have awesome food, no matter what your cravings and small shops throughout the area make shopping fun. The local history also plays a prominent role in this area. If you visit, be sure to bring a camera to capture images of wildlife, nautical scenery, and the most amazing sunsets! We’ll be back again most certainly and would recommend this spot to families as well as couples and individuals. Make your memories here!
Stayed 4 nights in Apr 2023

10/10 Excellent

sal g.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The cottage was clean, the discription was acurate,the attension to detail was outstanding.The rooms look like they were just renovated.The view from the deck was fantastic.The glasses, flatware and cookware looked new.Well worth the cost. There even was a binder with the history of the area and activity suggestions,We hated to leave.
Stayed 7 nights in Jul 2025

10/10 Excellent

William A.

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

Second year

Just as pleased as the first year
Stayed 7 nights in Jun 2025