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

Photo gallery for Kent Island Waterfront | Game Room | Private Dock | Pet Friendly

Main Level Entry.1
Dock
Lower Level Recreation Room.5
Main Level Deck
Main Level Living Room.4

Reviews

9.2 out of 10
Wonderful
4 bedrooms3 bathroomsSleeps 8323.8 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View map
Grasonville, MD
  • Place, Queenstown Premium Outlets
    ‪14 min drive‬
  • Place, Chesapeake Bay Environmental Center
    ‪14 min drive‬
  • Place, Queenstown Harbor Golf Club
    ‪15 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪33 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 /

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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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
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.
View more Holiday homes in GrasonvilleOpens in a new window
Map
Grasonville, MD

What's nearby

  • Queenstown Premium Outlets - 14 min drive - 12.3 km
  • Chesapeake Bay Environmental Center - 14 min drive - 10.0 km
  • Queenstown Harbor Golf Club - 15 min drive - 13.0 km
  • Chesapeake Exploration Center - 16 min drive - 14.2 km
  • Paul Reed Smith Guitars - 20 min drive - 20.8 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
  • ‪A Little Lovely Coffee House - ‬17 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 26 Mar 2026, prices found for a 1-night stay for 2 adults at Kent Island Waterfront | Game Room | Private Dock | Pet Friendly on 26 Mar 2026 start from AU$572, 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 Chesapeake Exploration Center. Rufus M and Loraine Hall Todd Performing Arts Center and Paul Reed Smith Guitars are also within 12 miles (20 km).

Reviews

9.2

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 8 out of 12 reviews
Rating 8 - Good. 3 out of 12 reviews
Rating 6 - Okay. 1 out of 12 reviews
Rating 4 - Poor. 0 out of 12 reviews
Rating 2 - Terrible. 0 out of 12 reviews

9.4/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Dawn F.

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

Quiet and relaxing

Beautiful property! Would highly recommend for a family to reacquaint and relax!
Stayed 4 nights in Aug 2024
Verified

8/10 Good

c b.

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

Relax

Had friends and family stay for 4 days. Nice house and dock.
Stayed 4 nights in Jul 2025
Verified

10/10 Excellent

Stacy B.

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

Perfect Serene Retreat!

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!
Stayed 3 nights in Jun 2022
Verified

10/10 Excellent

Carla E.

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

Enjoyable and relaxing get-away!

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!
Stayed 3 nights in Aug 2025
Verified

8/10 Good

T W.

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

Birthday Gathering

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 .
Stayed 3 nights in Jul 2024
Verified

10/10 Excellent

Sharon P.

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

Grasonville Home

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.
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

David H.

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

lovely place

i'm not sure why the fees are 39% - 2x other similar properties. i found this really grating.
Stayed 4 nights in Apr 2024
Verified

10/10 Excellent

Peg S.

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

Lovely getaway

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.
Stayed 3 nights in Apr 2021
Verified

8/10 Good

Michael O.

Liked: Check-in, communication, location, listing accuracy

Friends' reunion

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.
Stayed 3 nights in Oct 2022
Verified

6/10 Okay

jen s.

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

Reunion week

Beautifully house. Lots of space. Lovely backyard. Really enjoyed screened porch.
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Sean R.

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

Wonderful stay on the Eastern Shore

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.
Stayed 3 nights in Sep 2021
Verified

10/10 Excellent

Betsy W.

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

Great Getaway

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.
Stayed 6 nights in May 2021

About the host

Hosted by Eastern Shore Vacation Rentals

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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
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