Kent Island Waterfront | Game Room | Private Dock | Pet Friendly

Grasonville, Maryland
$859 avg/night
Bed 4

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 8

Max Sleeps

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 anicemaker, 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 /

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly Service Animals Exempt From Fees
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 3485 Sq Ft (324 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Kitchen Island Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Dock Garden Patio
  • BATHROOMS

    3 Bathrooms Towels Provided
  • THINGS TO DO

    Fitness Center Kayak On Site Water Sports Equipment
  • ENTERTAINMENT

    Arcade/game Room DVD Player Pool Or Billiards Table Table Tennis Smart TV With Cable/satellite Service
  • LIVING SPACES

    Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Playground
  • LOCATION HIGHLIGHTS

    Near The Bay
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 8

Map Map

School District Availability

Review Review

  • Carla E.

    Submitted Aug 5, 2025

    Stayed Aug 1, 2025

    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!

  • c b.

    Submitted Jul 14, 2025

    Stayed Jul 3, 2025

    Had friends and family stay for 4 days. Nice house and dock.

  • Dawn F.

    Submitted Sep 2, 2024

    Stayed Aug 29, 2024

    Beautiful property! Would highly recommend for a family to reacquaint and relax!

  • T W.

    Submitted Jul 30, 2024

    Stayed Jul 27, 2024

    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 .

  • David H.

    Submitted Apr 24, 2024

    Stayed Apr 19, 2024

    i'm not sure why the fees are 39% - 2x other similar properties. i found this really grating.

  • Michael O.

    Submitted Oct 17, 2022

    Stayed Oct 13, 2022

    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.

  • Sharon P.

    Submitted Jul 25, 2022

    Stayed Jul 16, 2022

    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.

  • jen s.

    Submitted Jul 19, 2022

    Stayed Jul 2, 2022

    Beautifully house. Lots of space. Lovely backyard. Really enjoyed screened porch.

  • Stacy B.

    Submitted Jun 12, 2022

    Stayed Jun 9, 2022

    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!

  • Sean R.

    Submitted Oct 19, 2021

    Stayed Sep 30, 2021

    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.

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Total

Includes taxes and fees
$859+
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