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.

How many holiday rentals are available around Sherwood?

Our 2019 accommodation listings offer a large selection of 102 holiday lettings around Sherwood. From 59 Houses to 29 Cabins, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

What is the best area to stay when travelling to Sherwood?

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Sherwood:

  • Epping Forest: 20 holiday homes
  • Winchester-on-the-Severn: 21 holiday homes
  • Eastport: 156 holiday homes
  • Naval Academy: 108 holiday homes
  • Historic District: 102 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday rentals available.

What are the most popular points of interest and landmarks to stay near when travelling to Sherwood?

HomeAway offers a large selection of holiday accommodations near great places in Sherwood. From HomeAway travellers, the most popular points of interest to stay near are:

  • Pickering Creek Audubon Center: 209 holiday lettings
  • Maryland Quiet Waters Park: 693 holiday lettings
  • Dorchester County Visitors Center: 163 holiday lettings
  • Westfield Annapolis Mall: 642 holiday lettings
  • Chesapeake Bay Maritime Museum: 399 holiday lettings

But there are many other points of interest around Sherwood listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent Houses in Sherwood?

Yes, of course. HomeAway offers 59 Houses in Sherwood. Our other popular types of Sherwood holiday rentals include:

  • Cabins: 29 self catering accommodations
  • Cottages: 29 self catering accommodations
  • Bungalows: 29 self catering accommodations

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

Can I find a holiday accommodation with pool in Sherwood?

Yes, you can select your preferred holiday accommodation with pool among our 54 holiday homes with pool available in Sherwood. Please use our search bar to access the selection of holiday rentals available.