Sherwood Vacation Rental Deals

There are a lot of options in Sherwood. If you plan on staying in the Sherwood area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cheap Hotels in Sherwood:

• Hurry, reserve your stay for nSummer & Fall of 2025nSTR #22-30
• Secluded Waterfront Property on 3 acres with swimming pool and dock.
• Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
• Private Retreat with HUGE Water Views!
• Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026!
• 6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
• Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock
• House on the Chesapeake Bay
• Heated pool, sandy beach, pier, and playground set punch point apart!
• GRATITUDE FARM - A Tranquil Waterfront Renovated Farmhouse - Bozman, MD

We have many pet-friendly cheap hotels and rentals in the Sherwood. The top pet-friendly rentals in Sherwood are:

• Knapps Narrows Marina & Inn
• St Michaels Area Cottage - Walk to Water and Marina
• The Tilghman Island Inn
• Wylder Tilghman Island

See all pet-friendly rentals in Sherwood on Barharborcabins

Yes, there are more than 71 cheap hotels and rentals in Sherwood that have indoor/outdoor and private swimming pools. Check out our filter option and find your best places to stay near Sherwood.

Most of the cheap holiday rentals have an internet facility on Barharborcabins. . These are some popular places to stay in Sherwood that have internet access:

• Knapps Narrows Marina & Inn
• St Michaels Area Cottage - Walk to Water and Marina
• The Tilghman Island Inn
• Wylder Tilghman Island

There are more than 71 cheap rentals with hot tubs available for rent in Sherwood.