Explore Diggs Wedding-Friendly Rentals

Planning to stay in Diggs? Consider booking your stay at one of these top-rated wedding-friendly vacation rentals:

• Gorgeous Waterfront Estate-Private Pool, Pier, Tennis Court, Firepit
• Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water
• Experience the Best of Mathews Riverfront Living here at Mariner's Legacy!
• Private, 7-acre waterfront retreat on Winter Harbor Haven
• PRIVATE BEACH on the Chesapeake Bay
• Beach House on Chesapeake Bay!
• The Harbor House - Waterfront Home with Private Pier & Amazing Views!
• Sunsets on the Mobjack and East River! Bring your kayaks & bikes.
• Beachfront Home on Chesapeake Bay - Gwynn’s Island
• Victorian Farmhouse w/private waterfront & pier at the mouth of Mobjack Bay

Explore a curated collection of vacation rentals featuring private pools near Diggs with Perfect for Weddings. Indulge in the ultimate luxury and serenity at our premier villas and holiday homes, offering exclusive access to tranquil swimming pools.

• Private, secluded waterfront cottage - pool and hot tub feet from the back door.
• Chesapeake Bay Waterfront Cottage Pool, Pier, Kayaks, Wifi 2 Bd/2 Ba, Mini Golf
• Chesapeake Bay Waterfront Cottage w/Pool, Pier, Kayaks, Mini golf, Wifi 1BR/1Bth

• Charming house with WiFi, AC in welcoming Mathews County on the Mobjack Bay.
• Blanchard Farm
• Leia's Folly, Mid-Century Modern Waterfront Retreat on the water w/kayaks & R2D2

As of 2025, Perfect for Weddings offers a diverse selection of over 75 properties listed in the Diggs area, with new additions regularly. By aggregating listings from multiple sources, Perfect for Weddings provides an extensive range of premier properties tailored for wedding groups in Diggs.