Annapolis: Vacation Rental By Owner

Located in safe residential neighborhood. Our backyard is a private wooded Oasis! Close to shopping, restaurants and the Chesapeake Bay. Minutes drive to... ...more

This Vintage 1930's Bay Front Beach House overlooks the Chesapeake Bay and Thomas Point Light House all the way to Kent Island! The sunrise colors and sounds of... ...more

This home is spacious and clean and will make your vacation plans a breeze from this central location. Many families, groups of friends, reunions, wedding... ...more

Come and enjoy this very cozy little Historic District house fully furnished just waiting for you! This three bedrooms, two and a half bath, with a garage for 2... ...more

This quaint little cottage is the perfect getaway retreat for a week. It has just what you need to stay there and enjoy your time in Annapolis. This unit is in... ...more

An Annapolis dream unit! This great garden-style condo is located in the gated Shearwater Community in Eastport with a fabulous deck overlooking Spa Creek. It is... ...more

Delightful Arts and Crafts/ Coastal style home. Main Level is open space concept with 9 ft ceilings and plenty of natural light, walk out to large yard and... ...more

Visit this expanded & completely renovated home at the end of a cul-de-sac featuring an open floor plan and large, private backyard with standalone bar & grill!... ...more

Five Star quality private home in the historic Murray Hill neighborhood of Annapolis, around the corner from the town center but in a quiet, quaint neighborhood.... ...more

EPS Location 1 and 2 With a stay at Extended Stay America Annapolis - Admiral Cochrane Drive in Annapolis, you'll be within a 15-minute drive of U.S. Naval... ...more

This luxiourious apartment sits right off Main Street and is so centrally located...you can park your car in the city garage and walk to everything. Great place... ...more

A Gorgeous, Waterfront setting in the Sailing Capital of the World! Charm, Detail, and Hospitality were not spared in this newly-remodeled and totally upgraded... ...more

The William Anderson House invites you, your family and friends to enjoy this stunning renovation of a semi-detached home located in the heart of Historic... ...more

0514 THE CREW HOUSE Nantucket meets Martha's Vineyard in this charming, recently renovated Eastport home impeccably decorated by a US Naval Academy family in the... ...more

0180 ANCHORS AWEIGH Perfect 4 Bedroom Historic Home. Located within a block of the William Paca House and Gardens and two blocks to Annapolis Harbor, St. Johns... ...more

Charming 3 bedroom home in quiet neighborhood next to stadium, city dock and walking trails. The home is 1.5 miles away from the Naval Academy Campus and 0.5... ...more

WATERSIDE with IT ALL. Private Pier, Pool & Hot Tub 6 Bedrooms, 5 1/2 Baths, 2 Fireplaces and ???????finished lower level walk out with In law Suite, 2 Full... ...more

0025 BELLA CHATEAU ???????Lot's of space! Entertaining space, dining space, outdoor space and sleeping space. Warm and inviting social rooms for gathering and... ...more

MAGICAL WATERFRONT Beautifully restored, turn of the century, beach cottage located on an acre of landscaped property with magnificent views of the Chesapeake... ...more

Historic Grandeur in the Heart of Downtown. Upscale historic residence situated on one of the most sought-after streets in downtown Annapolis. 5 large bedrooms... ...more