Escape to the serenity of Maryland's Eastern Shore at Windward Cove. Unwind in spacious rooms, enjoy waterfront views from the backyard deck, or challenge friends to a game of pool. Explore local crab houses and restaurants or take a quiet stroll along Little Greenwood Creek.
Reviews
9.29.2 out of 10
Wonderful
Entire home
4 bedrooms3 bathroomsSleeps 83485 sq ft
Popular amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free Wi-Fi
Air-conditioning
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.
Kent Island Waterfront | Game Room | Private Dock | Pet Friendly
Nestled in the charming village of Grasonville, Windward Cove offers an idyllic retreat for those seeking a blend of luxury and serenity. This stunning four-bedroom, three-bathroom waterfront home comfortably sleeps up to eight, making it perfect for families or groups of friends. The spacious layout includes an inviting living room with a gas fireplace, perfect for cozy evenings by the fire. The kitchen is a chef's dream, fully equipped with modern appliances including a refrigerator with an icemaker, a dishwasher, and a Keurig coffee maker, ensuring you have everything needed for a comfortable stay.
The bedrooms are generously sized and thoughtfully designed. The primary suite is located on the main floor, featuring a luxurious king bed and an en-suite bathroom with a luxurious bathtub. Two additional queen bedrooms share a hall bathroom, offering both privacy and convenience. An upper-level bedroom provides a quiet retreat with its own en-suite bathroom.
Outdoors, Windward Cove truly shines. The waterfront location on Little Greenwood Creek offers the perfect setting for fishing or simply enjoying the peaceful sounds of nature. A private dock with 1 tandem and 2 single kayaks allows for easy access to the water, while the backyard deck is ideal for barbecues and outdoor dining. The screened porch provides a perfect spot to unwind with a book or a glass of wine, while the grill is available for your cooking needs.
The home also features a well-equipped lower-level recreation room with a pool table, ping pong table, and a sectional sofa, making it an excellent space for games and relaxation. The sunroom offers additional seating and a tranquil space to enjoy the views. Additional amenities include a home gym, high-speed Wi-Fi, and cable TV, ensuring you have all the comforts of home.
Located just a short drive from Annapolis, you can explore historic sites and enjoy the vibrant city life. Kent Island beaches are perfect for a day of sunbathing and swimming, while the Chesapeake Bay offers opportunities for boating and fishing. The Cross Island Trail is a must-visit for outdoor enthusiasts, providing miles of scenic routes to hike or bike.
Windward Cove is not just a place to stay; it’s a place to create lasting memories. Whether you’re looking to relax by the water, explore the local attractions, or enjoy some friendly competition in the game room, this home offers the perfect setting for your getaway. Book your stay at Windward Cove today and experience the best of Maryland’s Eastern Shore.
PROPERTY FEATURES:
Waterfront: Little Greenwood Creek Dock: 40ft dock with 2ft MLW. Water and electricity are available for guest use. Water Toys: 1 tandem kayak and 2 single kayaks are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Fireplace: Gas fireplace is available for guest use. Gym: Home gym is available for guest use. Game Room: Pool table and ping pong table are available for guest use. Grill: Propane grill. Propane is provided. Pet Friendly: This is a pet friendly rental. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.
BED SIZES:
Queen - 1 / Queen - 1 / King - 1 / Double - 2 /
Property amenities
Internet
Available in the house: Free WiFi
Parking and transport
Parking on site
Kitchen
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Hob
Kitchen island
Microwave
Oven
Refrigerator
Toaster
Dining
Dining table
Bedrooms
4 bedrooms
Bedsheets provided
Bathroom
3 bathrooms
Towels provided
Living spaces
Dining table
Fireplace
Living room
Entertainment
DVD player
Smart TV with cable/satellite channels
Outdoor areas
Barbecue grill
Dock
Garden
Patio
Laundry
Laundry facilities
Washing machine
Comfort
Air conditioning
Heating
Pets
Pet friendly
Suitability/Accessibility
Smoke-free property
Location highlights
Near the bay
Things to do
Arcade/game room
Billiards/pool table
Gym
Kayak
Table tennis
Water sports equipment
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)
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
Pets are allowed
Service animals are welcome, and are exempt from fees
Children and extra beds
Children are welcome
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
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
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
About the area
Grasonville is home to this holiday home. St. Michaels Museum and Avalon Theatre are local landmarks, and some of the area's attractions include Rufus M and Loraine Hall Todd Performing Arts Center and Paul Reed Smith Guitars. Travelling with kids? Consider Chesapeake Bay Maritime Museum and Easton Cycle and Sport. Visit our Grasonville travel guide
Is Kent Island Waterfront | Game Room | Private Dock | Pet Friendly pet-friendly?
Yes, pets are allowed at this property.
How much is parking at Kent Island Waterfront | Game Room | Private Dock | Pet Friendly?
On-site parking is available at the property.
What time is check-in at Kent Island Waterfront | Game Room | Private Dock | Pet Friendly?
Check-in begins at 4:00 PM.
What time is check-out at Kent Island Waterfront | Game Room | Private Dock | Pet Friendly?
Checkout is at 10:00 AM.
Where is Kent Island Waterfront | Game Room | Private Dock | Pet Friendly located?
Set in Grasonville, this family-friendly holiday home is within 9 mi (15 km) of Chesapeake Bay Environmental Center, Queenstown Premium Outlets and Queenstown Harbor Golf. Rufus M and Loraine Hall Todd Performing Arts Center and Paul Reed Smith Guitars are also within 12 miles (20 km).
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Kent Island Waterfront | Game Room | Private Dock | Pet Friendly Reviews
Reviews
Wonderful
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Lovely serene home in a quiet neighborhood. Peaceful view of lakefront property. Only thing internet was a bit spotty at times and grill is rusty otherwise a great stay from the hustle and bustle of the city .
We were in town for a wedding and could not imagine a more perfect place to stay! The beautifully landscaped backyard and water view made for relaxing peaceful evenings on the screened in deck. It was perfect!
This house is beautiful. Wide open concept, basement full of activities for the entire family! The screened in porch was the spot for morning coffee and after dark hang out with the fire ring. Cooking in that kitchen was the best. Beds comfortable, and a very bright house with floor to ceiling windows. We had such a great time spending a few days there and would return again!
Perfect house for family vacation. We enjoyed long family dinners at large table which then became our game night table - when we weren’t downstairs in the game room having ping pong and pool tournaments. Easy drive to beaches and Annapolis. Large back yard and screened in porch made for early morning and late evening enjoyment.
Antsy to get away postCOVID so opted to visit old haunts around Kent Island. Got to visit friends & eat in some favorite restaurants.
House was immaculate and WAY MORE than the 2 of us needed but still felt warm & cozy. Fitness room is the best! Had a couple questions & received prompt responses from property mngmt company.
Well stocked kitchen & cleaning supplies.
We are three old friends who get together two or three times a year to hang out and prepare good food.
This place was mostly okay for the three of us but if there were many more some parts of it would not have worked very well. No place for 5 or more to sit comfortably in front of main TV.
The Weber grill needs to be either thrown away or totally rebuilt: the burners are rusted out and as a result I could not get the gas to vaporize properly and give a blue flame--instead there are yellow flare-ups from places where the burners are rusted out and emitting to great a supply of gas. it became almost impossible to prepare BBQ properly. Also the flavorizer bars are totally rusted out and in one or two places they are collapsed into the burners, making an already difficult job impossible.
The screened-in outdoor porch would have been nice to use as there were a number of insects flying around but it was filthy and had obviously not been washed in a long time, so we did not get to use it.
The rooms were comfortable and the kitchen adequately provisioned.
The rug under the dining table is a menace as two corners are curled up and are definite trippers, easy to miss when serving food from kitchen to table, etc. We put large objects on them to serve as obstacles.
On a scale of 1 to 10 I would give it a 6 to 7 at best. With some care it could be a 9.
Great property - massive lot with gorgeous, tree lined drive. Plenty of room for a multi generational family gathering of 8. Screened in porch with fire pit was perfect for the evenings. Huge basement and amazing kitchen. Wonderful, peaceful getaway. Property manager extremely responsive. Would stay again in a heartbeat.
We had a wonderful week connecting with family at Windward Cove. The house is very comfortable. We very much enjoyed the kayaks and the screened porch with the firepit.