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September 2025

October 2025

Find the best place to stay - The Colonial Players

Premier Host

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Sleeps 18 · 6 bedrooms · 4 bathrooms

Premier Host

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

Sleeps 16 · 6 bedrooms · 4+ bathrooms

Top rated rentals - The Colonial Players

ShipShape

A home away from home. This beautiful apartment has everything an independent holidaymaker could desire. Super clean and clever design for comfort and functionality. The location is perfect for sightseeing the Annapolis historic sites and nearby colleges.

Jenny d.

Stayed May 2023

Premier Host

Fantastic house - clean, warm & perfectly located to get around Annapolis

Property was fully equipped with everything we needed - like a ‘home away from home’. John was extremely helpful and informative during our planning and everything was as we expected. Thanks a lot!

Simon M.

Stayed Dec 2017

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