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Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

Elegant & Authentic Annapolis

Enjoy comfortable elegance in this historic beauty on one of the prettiest streets in Downtown Annapolis--Main Street and the Water only 2 blocks away. This private unit is the full main level with its own eat-in kitchen, living room, front porch and back patio. Bedroom features queen size bed, dresser and walk-in closet. Bathroom has shower/tub and counterspace for your comfort. Street parking is available or public garage parking is a short stroll away. Relish this quiet & convenient location.

Cozy 2br home w/ parking in downtown Annapolis

Ideally located in the heart of downtown Annapolis's Historic & Art Districts. Detached home with historic charm & an inviting front porch, 1 car parking included. Open floor plan to include a living room (with queen sleeper sofa), workspace, 1/2 bath & eat in kitchen on the 1st floor. 2 bedrooms and a full bath upstairs. Enclosed rear yard provides an opportunity to create a lovely quiet space out our back door. A perfect location for C-Week, Boat Shows & other festivals in Historic Annapolis.

Moose’s Happy Place

Built in 2019 with open spaces and happy places on historic Eastport Peninsula. A fresh take on coastal contemporary with front & back porches just steps from the Severn River & Spa Creek. Easy to enjoy the salty vibe with short walks to water access areas as well as Eastport's best local pubs and restaurants; or head over the Eastport bridge to downtown Annapolis and the Naval Academy - also accessible by water-taxi, rental boats & paddle-boards... A great NEW place in a great OLD place!!!

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Chesapeake Birdhouse Studio

Private, clean, cozy studio in the heart of Eastport, Annapolis. Quiet, separate, retreat space. Walk 1 block to restaurants and bars in Eastport, hop on the water taxi and you are in the heart of Downtown Annapolis, USNA, and historic areas of Annapolis in minutes. This is an Ideal location for the sailing community or anyone visiting our beautiful city. Free street parking available. You could park your car and never have to move it through out your stay. Walk, bike or water taxi.

Annapolis Waterfront Condo - Unit #: A-203

BOOK NOW FOR SUMMER 2025! SPRING and FALL BOAT SHOW AVAILABILITY! Free reserved parking! Walk to show in minutes! Great views - 2nd flr. condo (12 stairs, no elevator.) Pool hours are fixed: Mon: 4pm-8 Tues: Closed Wed: 4-8 Thurs: 4-8 Fri: 3-8 Sat/Sun/Holidays: 12pm-8 The pool is one of the best places to be on a hot summer day. If hours are unacceptable, pls select another location. 15 min. walk to downtown Annapolis/USNA. MULTIPLE Free parking options.

Charming Eastport

Who needs a boat to stay at a marina? Eastport Yacht Center has a quaint one bedroom apartment located in charming Eastport, within walking distance to Downtown Annapolis and the U.S. Naval Academy. Conveniently located next to the Annapolis Maritime Museum. (Two guests maximum) If this apartment isn't available for your time period check out our other studio apartment listed under "NEW lovely studio apartment with onsite parking".

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.