Find vacation homes for rent in Maryland lifestyle communities

Maryland Vacation Home Rentals

Maryland vacation rentals in master-planned communities offer a wonderful experience for visitors seeking a blend of recreation, relaxation, and culture. Renting a vacation home in a lifestyle community in Maryland offers proximity to historic landmarks and cultural attractions—near historic sites such as Annapolis, Baltimore, and Washington D.C. In addition to the wealth of opportunities to learn about the state's rich history and cultural heritage, Maryland is also known for its waterfront attractions like Chesapeake Bay’s beaches and marinas. Many Maryland communities are located near the water, providing guests with access to water sports such as kayaking, paddleboarding, boating, and fishing.

Resort-style vacation home rentals within communities come with the added bonus of onsite amenities like golf, fitness centers, swimming pools, and more. Explore these Maryland communities with vacation homes for rent to learn more.

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Lakeside at Trappe

Trappe, Maryland Vacation Home Rentals
Trappe, Maryland

Situated on the Eastern Shore of Maryland in Talbot County, Lakeside at Trappe is a private master-planned community for all ages. Residents have immediate access to Route 50 with proximity to Annapolis, Easton, and local beaches. Resort-style amenities include an on-site lake, clubhouse, sports courts, swimming pool, fitness center, dog park, and more. Home designs include townhome and single-family floorplans up to 3,700+ square feet, 6 bedrooms and 4 bathrooms with options for main-level living. Priced from the $300,000s and up. Home leases are available starting in the $2,000s/month. Read More...

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Swan Point

Swan Point, Maryland Vacation Home Rentals
Swan Point, Maryland

Swan Point is a resort golf and waterfront community in Swan Point, MD. Located about 50 miles south of Washington, D.C., in Chester County, the Southern Maryland community is situated on the Potomac River and Cuckold Creek epitomizing premier Maryland waterfront living. Amenities include a marina, clubhouse with dining options, championship golf course, tennis, pickleball, swimming pool, and walking trails. Developed by Brookfield Residential, the innovative home designs offer several floorplans with buying and leasing options. The unique Maryland real estate ranges from 2,469 – 3,527 square feet with homes priced from the $500,000s. Read More...

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