Beach Home Rentals in Grimstead, VA: Compare 10+ Sites & Save

Some of the best beach rentals in Grimstead are:

• Gwynn's Island Cottage w/ Private Beach-Summer Weeks Open!.- Review Count: 220, Rating: 10.0
• PRIVATE BEACH on the Chesapeake Bay .- Review Count: 138, Rating: 10.0
• Sand and Sun Beachfront Home on Chesapeake Bay - Gwynn’s Island, Mathews County.- Review Count: 49, Rating: 10.0
• Private Beach - Peaceful Retreat - Kayaks Bicycles Firepit and Pet-Friendly!.- Review Count: 35, Rating: 10.0
• New 5 bedroom home on private, sandy beach with game room and elevator. .- Review Count: 5, Rating: 10.0
• Cozy little home on Gwynn's Island with semi-private Chesapeake Bay beach access.- Review Count: 4, Rating: 10.0
• Bayfront Escape, Private Dock, Large Deck, and Views!.- Review Count: 4, Rating: 10.0

You can explore 8 verified beach rentals in Grimstead. Our listings are sourced from trusted booking providers, giving you access to a wide selection of oceanfront homes, seaside condos, and coastal stays—all in one place.

Beach rental prices in Grimstead vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $261 per night, with beachfront properties and peak summer dates often priced higher. Comparing available options can help you find the best fit for your budget.

Many beach rentals in Grimstead offer direct access to the sand or are located within a short walking distance of the shoreline. You can use filters to find properties with beachfront locations, private walkways, or unobstructed ocean views.

Yes, many beach rentals in Grimstead welcome pets. Currently, 4 listings allow pets, although policies may vary by property. It’s also a good idea to check local beach regulations for any restrictions on pets during your stay.

For peak travel periods such as summer holidays or spring break, it’s recommended to book your beach rental 90 to 120 days in advance to secure the best options. During off-peak seasons, you may find more flexibility and availability closer to your travel dates.

Beach rentals in Grimstead often include amenities designed for coastal living, such as Ocean View, View, and Fireplace/Heating. These features help enhance comfort and make it easier to enjoy time by the water.

Some beach rentals provide extras like chairs, umbrellas, or beach gear, but this can vary by property. It’s best to review the amenities section of each listing to confirm what is included and plan accordingly.