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 travelers with its sailing and restaurants. If you need more space to accommodate a family vacation or friends trip, 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 vacation rental, you'll want to check out everything that makes Sherwood a one-of-a-kind vacation spot. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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 center:

  • 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

Transportation 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 center. 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 vacation rentals are available around Sherwood?

Our 2019 vacation rental listings offer a large selection of 104 house rentals around Sherwood. From 61 Houses to 29 Cabins, find unique vacation rental for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Sherwood is on HomeAway.

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

Whether you're travelling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Sherwood:

  • Eastport: 157 vacation rentals
  • Historic District: 103 vacation rentals
  • West Annapolis: 38 vacation rentals
  • Hillsmere: 17 vacation rentals
  • Epping Forest: 20 vacation rentals

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

What are the popular points of interest near where I can stay when travelling to Sherwood?

HomeAway offers a large selection of lodging choices near lovely places in Sherwood. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Chesapeake Bay Bridge: 640 home rentals
  • Chesapeake Bay Maritime Museum: 403 home rentals
  • Spocott Windmill: 196 home rentals
  • Choptank River Lighthouse: 168 home rentals
  • Chesapeake Bay Environmental Center: 635 home rentals

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 vacation rentals available near the point of interest of your choice.

Can I rent Houses in Sherwood?

Yes, of course. HomeAway has 61 Houses in Sherwood. Our other popular types of vacation rentals in Sherwood include:

  • Cabins: 29 lodging choices
  • Cottages: 29 lodging choices
  • Bungalows: 29 lodging choices

But you can also enjoy a great stay in one of our other vacation homes 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 55 vacation homes with pool available in Sherwood.

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