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.

Interesting in earning more from your rental? Learn about our full-service Annapolis property management program and meet our team.

An Ocean City vacation rental puts your family in the middle of entertainment and fun! iTrip Vacations Ocean City manages rentals in this popular resort destination located along Maryland's eastern coast.

Ocean City earned a spot on TripAdvisor's top 10 beaches, and it's easy to see why. The area features over 10 miles of beaches, amusement parks, exciting attractions and natural areas. Located between the Atlantic Ocean and Isle of Wight Bay, guests have access to water activities and beach-loving vibes. Outdoor enthusiasts enjoy boating, fishing, jet skiing, kayaking, parasailing and relaxing in the sun. Sport-fishing fans can attend and compete in the White Marlin Open, named the largest and richest billfish tournament in the world with top prizes reaching $1.6 million.

While exploring, visit Ocean City Boardwalk, a historic site packed full of games, restaurants, nightlife and shops. Day or night, the boardwalk promises entertainment for the whole family. In the summer, visitors enjoy free family activities, concerts, movies and beach fun. Ocean City Boardwalk has even earned accolades from the Travel Channel and USA Today. For additional sites and big savings, drive 25 miles north to tax-free shopping at Tanger Outlets Rehoboth in Delaware.

Need more adventure? Head to the amusement parks. Top options are Trimpers Rides and Amusement Park, Jolly Rogers, and Frontier Town, all offering different experiences. Trimpers features carnival-style rides and thrilling roller coasters. Meanwhile, Frontier Town immerses guests into Wild West culture as they see lively shows and play at the waterpark. Jolly Rogers welcomes guests to enjoy rides, racetracks and iconic treats like Thrasher's fries and funnel cakes.

Golfers admire rolling greens at 17 championship golf courses near Ocean City. Each course offers scenic views, challenging holes and natural landscape. Eagles' Landing – one of the best courses in the area – has been named the No. 1 course in Maryland by GolfAdvisor and features 7,000 yards set among lakes, ponds, trees and saltwater marshes. Or test your swing at Bay Club, GlenRiddle, Links at Lighthouse Sound and Ocean Pines.

Those interested in attending an Ocean City event find over a dozen signature festivals. From cars to wine, the city celebrates what makes it a great destination. In the spring, plan your Ocean City vacation around Springfest, showcasing arts, crafts and live music. In the summer, Cruisin' Ocean City and the Fourth of July celebrations delight guests. Other festivals you can't miss include Sunfest, OC Bike Fest and Winterfest of Lights in the winter.

Sample flavors from around the world – and Maryland's famous blue crab cakes – at over 200 Ocean City restaurants. From diners to upscale waterfront restaurants, your group will feast like a king. Over 80 top-rated restaurants serve fresh seafood, so come hungry for crab, local catches, shrimp and different takes on cuisine. The area also offers a large selection of authentic pizza restaurants perfect for a casual night out with the family.

Night owls also have several places to kick back, as Ocean City houses dozens of bars and clubs where you can dance or karaoke into the early morning hours. For special shows and events, visit the Performing Arts Center, which hosts live music, ballet, children's plays, symphonic performances and more.

It's time to plan! View available Ocean City vacation rentals.

Want to increase your vacation rental income? Contact our Ocean City property management team.