Sherwood Rentals By Owner

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 Vacation Rentals in Sherwood:

• Overlook on Dun's Cove - Luxury waterfront hideaway minutes from St. Michaels
• Hurry, reserve your stay for nSummer & Fall of 2025nSTR #22-30
• Secluded Waterfront Property on 3 acres with swimming pool and dock.
• Private Retreat with HUGE Water Views!
• House on the Chesapeake Bay
• SUMMER DATES BOOKING FAST- BOOK YOUR STAY NOW!
• Grandview- Main House
• BOOK NOW FOR SPRING & SUMMER DATES.
• Mill Point
• Amazing Waterfront Views, Private Pool and Dock

There are many large, family-friendly vacation homes available in Sherwood; however, here are the most popular family rentals listed on our site:

• Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
• St Michaels Area Cottage - Walk to Water and Marina
• Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026!
• Waterfront Bliss- Ultimate Tilghman Retreat home

Yes, there are 55 self-catering vacation homes in Sherwood that have hot tubs, swimming pools, & other amenities.

There are more than 55 luxury villas and vacation homes in or near Sherwood. Filter by price to compare find the most expensive places to stay on Lakemichigancabins.

Yes, there are 55 pet friendly vacation homes and places to stays that are available in or near Sherwood that you may consider.