This is where your adventure on the water begins! We’ve got all the information you need about the top companies for boat rentals in Annapolis, MD. Discover the possibilities and get one step closer to the beauty of the Chesapeake Bay. By the time you get back to shore, you’ll have memories to last a lifetime. Just make sure there’s a beautiful vacation rental waiting for you back on land. Browse our selection of properties in Annapolis and find the ideal retreat for your next getaway!

Annapolis Electric Boat Rentals

There are no surprises here — this company has you covered with electric boat rentals in Annapolis! Their 22-foot long boats are perfect if you’re looking to slow things down, enjoy the scenery, and spend quality time with your friends and family. The boats are easy to handle, but AEBR goes the extra mile by providing in-depth instruction to make sure you feel completely comfortable driving it. Plus, the canopy on top of each boat provides some pleasant shade during those hot, sunny days on the water.

South River Boat Rentals

Another fantastic option is South River Boat Rentals in nearby Edgewater, MD. They offer 25 different boats to choose from with round-the-clock service available. Whether you’re looking to go sailing, fishing, or celebrate a special occasion on a luxury yacht, they’ve got you covered. They even provide gear if you’d like to try some fun watersports!

Paddle or Pedal

Paddle or Pedal has everything you need for adventures by land and by sea all in one convenient place. Check out their Annapolis location, Quiet Waters Park, to pick out your favorite pedal boat, sailboat, kayak, canoe, bicycle, and more. They have flexible rental options and convenient lessons available, too!

The List Goes On!

The options for charters and boat rentals in Annapolis, MD, don’t stop there. If you haven’t found what you’re looking for yet, consider checking out some of these great companies in the area:

  • Kayak Annapolis
  • Annapolis Canoe and Kayak
  • Dream Yacht Charter
  • Classic Sail Charters
  • Cruise Annapolis
  • Dancer Sportfishing Charters

Find the Perfect Vacation Rental for Your Visit to Annapolis

There’s nothing better than spending a day out on the water, then returning for an evening of luxury inside a beautiful vacation home. It’s not a daydream — it’s a reality with Eastern Shore Vacation Rentals! We have options for every budget and all group sizes in Annapolis, Maryland. Plus, we’re always adding more! Head over to our properties page to view the possibilities and make your dream vacation come true. Just don’t forget to book direct and browse our list of current specials to get the best deal on your stay!

Nantucket on the Chesapeake

Fore! An incredible golf getaway is headed your way! It’s time to dust off your clubs and practice your swing so you can play at these beautiful golf courses on the Eastern Shore of MD. It doesn’t matter if it’s your first time playing or your hundredth, you’re in for an incredible experience. Find out everything you need to know about each golf course and book a vacation rental nearby to enjoy the ultimate Eastern Shore vacation!

Discover Some of the Best Golf Courses on Maryland’s Eastern Shore

Hog Neck Golf Course

One of the most popular places to play is the Hog Neck Golf Course in Easton, MD. In fact, Hog Neck offers both an 18-hole, par 72 championship course as well as a 9-hole, par 32 executive course for you to enjoy. Warm up with their large putting green area, chipping complex, and driving range before starting a round. Even if you don’t score a hole-in-one, you can still reward yourself with some excellent food and drinks at the Hog Neck Café!

River Marsh Golf Club

Another excellent course awaits in Cambridge, Maryland. The River Marsh Golf Club is home to a beautiful, 18-hole course that’s open year-round to the public. While all 18 holes offer a challenging yet enjoyable experience, the last two are the true highlights. They provide a stunning finale to your round of golf with masterfully designed elements and gorgeous views of the Choptank River!

Queenstown Harbor Golf

Take your pick from the windswept River Course on the Chester River and the challenging Lakes Course. Both of these offer incredible settings for a game of golf at Queenstown Harbor. The well-stocked pro shop and the friendly staff put it over the edge to become one of the go-to golf destinations on the Eastern Shore of Maryland.

Blue Heron Golf Course

The Blue Heron Golf Course opened in 1959 and has provided a fantastic experience to golfers ever since. Blue Heron features a driving range, pro shop, refreshments, lessons, and much more in Stevensville, Maryland. This par 63 course features shorter holes for a slightly faster paced round that both beginners and veterans can enjoy.

Stay Near Your Favorite Courses

If you’re up for a golf getaway on Maryland’s Eastern Shore, we’ll help you enjoy it to the fullest! Our wide variety of vacation rentals includes historic cottages, waterfront homes, and beautiful estates that don’t just suit your needs — they go above and beyond expectations. Many of them feature gorgeous views and soothing pools that are perfect for unwinding after a full day of golfing. Plus, we offer several properties with flexible dates, including just three-night minimums, so you can always escape for a weekend of golf! Simply put, you can’t beat the comfort and convenience of Eastern Shore Vacation Rentals.

Browse our properties today and get one step closer to your happy place!

Blue Gates


Are you ready for an adventure? We’ll help guide the way with local tips on some of the most popular bike trails on Maryland’s Eastern Shore. A bike ride here is more than just a great way to get some exercise. It’s a fantastic opportunity to visit historical sites, admire nature, and enjoy breathtaking views of the Chesapeake Bay. Read on to find out which bike trail is right for you, and book one of our exceptional vacation rentals nearby so that you can unwind in comfort after your journeys.

Explore Maryland’s Eastern Shore on These Bike Trails

Some of the best bike trails in the area run throughout Talbot County. Here’s an overview of each one:

School Days

First on the list is the School Days bike trail. This scenic route begins in Easton, MD, and leads you to various historical sites, including a schoolhouse from 1865, a Civil War cemetery, and an environmental center where people have spotted over 200 species of birds. If you enjoy birdwatching, this is the bike trail for you. Bring binoculars to see if you can catch glimpses of bald eagles, herons, egrets, and more!

Distance: 28.3 miles

Starting Point: Rails to Trails parking lot in Easton

Highlights: Little Red Schoolhouse, Unionville Cemetery, and the Pickering Creek Audubon Center

Joust Maryland

Did you know that the state sport of Maryland is jousting? That’s actually where this trail got its name! Start your journey in Wye Mills and don’t forget to stop at the St. Joseph’s Church along the way. It’s the venue for the annual Jousting Tournament and Horse Show, which has been running for over 150 years!

Distance: 26.7 miles

Starting Point: Wye Oak State Park in Wye Mills

Highlights: Wye Oak State Park, St. Joseph’s Church, and Wye Landing

Talbot Farmland

Another fantastic option is the Talbot Farmland trail with gorgeous views and wide-open spaces in an agricultural atmosphere. There are a few side trails to explore which take you to Covey’s Landing, Reeses Landing, or Kingston Landing, all of which feature views of the Choptank River. The bridge at King’s Creek is also a lovely area for birdwatching!

Distance: 27.6 miles

Starting Point: Rails to Trails parking lot in Easton

Highlights: Choptank River and the King’s Creek bridge

Chesapeake Views

Chesapeake Views is a down-and-back trail that runs through Claiborne, McDaniel, Wittman, Sherwood, and Tilghman. It’s a longer trail than the others, but the beauty of the Chesapeake Bay waterfront makes it more than worthwhile.

Distance: 38.2

Starting Point: Claiborne Landing in Claiborne

Highlights: Charming small towns and waterfront views

Oxford/St. Michaels

The Oxford/St. Michaels bike trail is known as one of the top bike trails in the region, and even the country! Start in the beautiful town of St. Michaels and see a variety of historic communities along the way, including Oxford, Royal Oak, and Easton. Keep in mind that this trail requires a ferry ride which is only available from the spring to the fall.

Distance: 29.6 miles

Starting Point: Chesapeake Maritime Museum in St. Michaels

Highlights: Waterfront views, charming communities, and the Oxford Bellevue Ferry

Cemetery Quest

Last but not least is Cemetery Quest, which begins in Easton and runs for a total of 28.1 miles in a scenic loop. The “Quest” is to find all of the cemeteries along the path. Will you find them all?

Distance: 28.1 miles

Starting Point: Rails to Trails parking lot in Easton

Highlights: Historic cemeteries and wetland forests for birding

Rest Your Legs at a Beautiful Vacation Rental Nearby

If you need a place to stay for your Eastern Shore adventures, we have you covered! Eastern Shore Vacation Rentals has over 60 gorgeous properties in St. Michaels, Cambridge, Oxford, Tilghman Island, and beyond. Many of them feature pools, waterfront views, and easy access to your favorite activities while offering a peaceful escape from it all. We even offer pet-friendly options so that you never have to leave your loyal pal behind. Let us help you enjoy the scenery and serenity of Maryland’s Eastern Shore. Browse our selection of vacation rentals today and find your happy place!