Book an Annapolis vacation rental and visit Maryland's state capital! iTrip Vacations Annapolis manages short-term rentals in Annapolis, Kent Island and St. Michaels.
Due to its Chesapeake Bay location, water recreation is big in Annapolis. Add the city's 533-plus miles of creeks, rivers and streams, and there are plenty of reasons to play on the water. Start by canoeing, kayaking and stand-up paddle-boarding. Those who want guided options should plan a sailing tour and pirate cruise or ride water taxis. Other outdoor recreation includes boating, beach-combing, crabbing, fishing, wind surfing, playing at parks, and watching sporting events at Navy-Marine Corps Memorial Stadium.
When not on the water, learn and have fun. Annapolis offers attractions for all interests, so visitors may customize their adventure. Affectionately known as the “Sailing Capital of the U.S.,” Annapolis also houses the U.S. Naval Academy, which offers tours. Then tour Maryland State House, Annapolis Historic District, museums and churches. Area trolley tours provide an easy way to see everything while learning about the area's history and legends.
Visitors will also find coastal charm and history in nearby St. Michaels. This pet-friendly town offers a place to enjoy outdoor recreation and sports, tour museums and galleries, and shop local boutiques. St. Michaels also serves as a go-to place for community festivals and weddings, waterfront dining, and spas.
For an added adventure, book a Kent Island vacation rental. Kent Island ranks among the largest islands in Chesapeake Bay and offers outdoor recreation, parks, beaches, distilleries and vineyards. In addition, Kent Island has historical sites and provides access to the historic Stevensville Arts and Entertainment District.
Our Annapolis vacation rental guests also enjoy the area's arts and culture scene. Head to West Street for art galleries, music venues, classes, special events and dining. Visitors also enjoy celebrating art through theater, opera, symphony, ballet and live performances. Those who want to make a night of it will find quaint streets lined with bars, pubs, waterfront dining, and plenty of live music.
Forget something? Want to buy souvenirs? Don't miss Annapolis' shopping scene. The area has both big-box and boutique retailers as well as antique stores. For big names, browse stores at Annapolis Town Centre, Westfield Annapolis Mall and Arundel Mills Mall. During spring and summer, shoppers flock to Main Street, Maryland Avenue and Eastport, which sits a short drive from downtown Annapolis.
In addition, our Kent Island and Annapolis vacation rentals provide everyone access to delicious food, especially Maryland's famous blue crabs. This coastal destination has a stellar reputation for seafood, but also offers traditional and international cuisine. To sample some of the best local flavor, attend Annapolis Crab Fest and Annapolis Restaurant Week, or schedule a guided food tour.
But wait. There's more! Annapolis also hosts more than a dozen festivals that celebrate the best in culture, sports and coastal living. Signature events include Annapolis Film Festival, Boat Maryland Week, Maryland Day, sailboat shows, a Renaissance festival and football. Guests also love the holiday celebrations, tree lightings, fireworks, boat parades and light displays.
Plan a trip! Book an Annapolis area vacation rental and start planning.
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