Top-rated for comfort — guests feel right at home here.
Arcade/game room
A rare find - fun for all ages with on-site arcade/game room.
Your private hideaway
Guests love the secluded location for peace and quiet.
Sleeps 8•4 bedrooms
Popular amenities
Onsite parking available
Pet-friendly
Kitchen
Washing machine
Air-conditioning
Barbecue grill
Explore the area
Grasonville, MD
Chesapeake Bay Environmental Center
Place, Chesapeake Bay Environmental Center
14 min drive
Queenstown Premium Outlets
Place, Queenstown Premium Outlets
15 min drive
Queenstown Harbor Golf
Place, Queenstown Harbor Golf
17 min drive
Easton, MD (ESN-Easton - Newnam)
Airport, Easton, MD (ESN-Easton - Newnam)
40 min drive
Rooms & beds
4 bedrooms (sleeps 8)
3 bathrooms
Bathroom 1
Bathroom 2
Bathroom 3
Spaces
Deck or patio
Kitchen
Outdoor play area
Garden
About this property
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 /
Our prices include all fees. No hidden fees.
Add dates for prices
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Similar properties
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit
Grasonville
Private Riverfront Home with Hot Tub, Kayaks, Paddleboards and Riverside Firepit
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.
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
About the area
Grasonville
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.
Chesapeake Bay Environmental Center - 14 min drive - 10.0 km
Queenstown Premium Outlets - 15 min drive - 12.3 km
Queenstown Harbor Golf - 17 min drive - 14.0 km
Chesapeake Exploration Center - 17 min drive - 14.2 km
Matapeake State Park - 25 min drive - 25.3 km
Getting around
Easton, MD (ESN-Easton - Newnam) - 32 min drive
Restaurants
Wawa - 15 min drive
Royal Farms - 17 min drive
7-Eleven - 13 min drive
The Jetty Restaurant & Dock Bar - 16 min drive
Carmine's N.Y. Pizza Kitchen - 18 min drive
Frequently asked questions
Is Kent Island Waterfront | Game Room | Private Dock | Pet Friendly pet-friendly?
Yes, pets are allowed at this property.
How much does it cost to stay at Kent Island Waterfront | Game Room | Private Dock | Pet Friendly?
As of 22 Aug 2026, prices found for a 1-night stay for 2 adults at Kent Island Waterfront | Game Room | Private Dock | Pet Friendly on 26 Jan 2027 start from £2,164, 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 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).
About the host
Hosted by Eastern Shore Vacation Rentals
What makes this property unique
4-BR, 3-BA, Sleeps 8, Creekfront House, Private Dock, Game Room, Grill, Home Gym
Premier Host
They consistently provide great experiences for their guests