See all properties
Entire home

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

Family-friendly stay with in-room kitchens in Grasonville

Choose dates to view prices

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

Interior
Interior
A spacious living room with a fireplace, a dining area, and a kitchen with a large island.
Dining
Fridge, microwave, oven, stovetop

Reviews

8.8 out of 10
Excellent

Entire home

4 bedrooms3 bathroomsSleeps 83485 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Grasonville, MD
  • Place, Chesapeake Bay Environmental Center
    ‪14 min drive‬
  • Place, Queenstown Premium Outlets
    ‪15 min drive‬
  • Place, Queenstown Harbor Golf
    ‪17 min drive‬
  • Airport, Easton, MD (ESN-Easton - Newnam)
    ‪40 min drive‬

Room options

You may also like

Ad
Property amenity

Courtyard by Marriott Annapolis

18.5 mi from Grasonville
  • Pool
  • Hot tub
  • Pet friendly
  • Free WiFi
8.6 out of 10, Excellent, 1,004 reviews
$110 nightly
The price is $125
Jul 26 - Jul 27
Total with taxes and fees
Courtyard by Marriott Annapolis

About the neighborhood

Grasonville

In Grasonville .At this Grasonville vacation home, you'll be within 6 miles (10 km) of Chesapeake Bay Environmental Center and 9 miles (15 km) of Queenstown Premium Outlets. Also within 9 miles (15 km) are Chesapeake Exploration Center and Queenstown Harbor Golf.
View more Vacation Homes in GrasonvilleOpens in a new window

What's nearby

  • Chesapeake Bay Environmental Center - 14 min drive - 6.2 miles
  • Queenstown Premium Outlets - 15 min drive - 7.7 miles
  • Queenstown Harbor Golf - 17 min drive - 8.7 miles
  • Chesapeake Exploration Center - 17 min drive - 8.8 miles
  • Paul Reed Smith Guitars - 22 min drive - 13.1 miles

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
  • ‪Anchor Drop - ‬13 min drive
  • ‪The Jetty Restaurant & Dock Bar - ‬16 min drive

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 /

Similar properties

Meeting facility
Historic Inns of Annapolis
Historic District
  • Pet friendly
  • Free WiFi
  • Restaurant
  • Air conditioning
4.5 out of 5, Wonderful, 1,893 reviews
$130 nightly
The price is $148
Jul 19 - Jul 20
Total with taxes and fees
Historic Inns of Annapolis

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • 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

  • Smoking not allowed

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)

General

  • Garden
  • Unit size: 3,485 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

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 welcome
  • Service animals 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

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector and a smoke detector in each accommodation.

Property is also known as

86
Vrbo Property

Frequently asked questions

How close is Kent Island Waterfront | Game Room | Private Dock | Pet Friendly to the airport?

This vacation home is 22.2 mi (32-min drive) away from the Easton, MD (ESN-Easton - Newnam) airport, the closest popular airport to the property.

Does Kent Island Waterfront | Game Room | Private Dock | Pet Friendly have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Kent Island Waterfront | Game Room | Private Dock | Pet Friendly to the beach?

This vacation home is 17 mi (33-min drive) from Earle Landing.

Does Kent Island Waterfront | Game Room | Private Dock | Pet Friendly offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Kent Island Waterfront | Game Room | Private Dock | Pet Friendly?

No, there is no casino at this vacation home.

What time is check-in at Kent Island Waterfront | Game Room | Private Dock | Pet Friendly?

Check-in begins at 4:00 PM.

Is there free parking at Kent Island Waterfront | Game Room | Private Dock | Pet Friendly?

Free parking is not available at this vacation home.

Does Kent Island Waterfront | Game Room | Private Dock | Pet Friendly have a pool?

This vacation home does not have a pool.

Does Kent Island Waterfront | Game Room | Private Dock | Pet Friendly have a spa?

There are no spa services available at this vacation home.

How close is Kent Island Waterfront | Game Room | Private Dock | Pet Friendly to downtown Grasonville?

This vacation home is 3.6 mi away from Grasonville.

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

Reviews

8.8

Excellent

Rating 10 - Excellent. 9 out of 14 reviews
Rating 8 - Good. 3 out of 14 reviews
Rating 6 - Okay. 1 out of 14 reviews
Rating 4 - Poor. 0 out of 14 reviews
Rating 2 - Terrible. 1 out of 14 reviews

9.6/10

Cleanliness

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

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

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

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

Explore More Ways to Travel with Travelocity