A large brick house with a green roof, surrounded by lush gardens and trees.

Sherwood houses

We found 163 houses — enter your dates for availability

Explore Sherwood house rentals

Image of Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Premier Host

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Sleeps 12 · 8 bedrooms · 8+ bathrooms

Image of 6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Premier Host

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Sleeps 12 · 6 bedrooms · 4+ bathrooms

Image of Heated pool, sandy beach, pier, and playground set punch point apart!

Premier Host

Heated pool, sandy beach, pier, and playground set punch point apart!

Sleeps 10 · 5 bedrooms · 4+ bathrooms

Image of Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels

Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels

Sleeps 4 · 2 bedrooms · 2 bathrooms

Image of ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS
PET FRIENDLY

ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS PET FRIENDLY

Sleeps 10 · 5 bedrooms · 4+ bathrooms

Image of Amazing Waterfront Views, Private Pool and Dock

Amazing Waterfront Views, Private Pool and Dock

Sleeps 12 · 6 bedrooms · 7+ bathrooms

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