Discover a selection of 104 holiday rentals in Sherwood, MD, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at £ 121 per night, and cottages and houses are popular options for a stay in Sherwood. Either way, you'll find a rental for everyone's needs.
Destination guide

Take in the natural beauty of Sherwood

The island views and riverfront create a pretty picture of Sherwood. This scenic and welcoming city entices travellers with its sailing and restaurants. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.


Activities and attractions in and around Sherwood

Do you want to discover attractions to visit in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Sherwood a one-of-a-kind holiday spot. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • St. Michaels Winery (6.2 mi / 10 km)
  • Chesapeake Beach Water Park (11.8 mi / 18.9 km)
  • Hog Neck Golf Course (15.6 mi / 25.1 km)
Natural features

Exploring the natural features in Sherwood

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Sherwood is a great place to get out in nature. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Shadyside Park (12.2 mi / 19.7 km)
  • Breezy Point Beach (13.3 mi / 21.4 km)
  • Kent Island (13.7 mi / 22.1 km)
  • Maryland Quiet Waters Park (16.2 mi / 26 km)
How to get there

Transport options to and around Sherwood

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 14.9 mi (23.9 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), which is 51.9 mi (83.6 km) away.

Can I find a vacation rental around Sherwood?

Yes, our 2021 property listings offer a large selection of 104 vacation rentals near Sherwood. From 21 cottages to 93 houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Sherwood for a holiday or a weekend are on Vrbo.

Can I rent Cottages in Sherwood?

Yes, of course. Vrbo UK has 21 Cottages in Sherwood. Our other popular types of vacation rentals in Sherwood include:

  • Houses: 93 rentals available
  • Cabins: 21 rentals available
  • Bungalows: 21 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Estates and more.

Can I find a vacation rental with pool in Sherwood?

Yes, you can select your preferred vacation rental with pool among our 50 vacation rentals with pool available in Sherwood. Please use our search bar to access the selection of vacation rentals available.