Holiday rentals in Hawkins Cove

Gybeset Eastport Inn

Enjoy exclusive use of this boutique hotel-styled upstairs apartment in a beautifully restored 1930s craftsman-style building in the heart of Eastport. Private off-street parking. Short walk to downtown Annapolis. Just a few doors away from one of the hottest restaurants in Annapolis, Vin 909. A seasonal farmers' market is located across the street along with restaurants and other amenities. Hotel-like services available for longer stays. Fully licensed by City of Annapolis for AirBnb operation.

Charming City Retreat. Walk-harbor, eateries.USNA

As many others over the past decade, you will enjoy the year-round charm & convenience of this modern vintage cottage. Just blocks from shops, restaurants, pubs. Free parking. A secluded patio oasis for family gatherings, a chimnea & blankets to cozy up in, furnishings from Robert Redford's Sundance, modern appliances, ceiling fans, AC/heat, bathrooms with comfort-height toilets & grab bars, original pine floors. Corn Hole boards on site. Open USNA '29 '30 Com Wk. 6-night min applies.

Hidden Wine Cellar | Eastport Retreat

There's a secret downstairs - a hidden wine cellar tucked beneath this Eastport home. Upstairs you'll find 2 bedrooms, a screened porch for lazy mornings, and a full kitchen with gas stove. Out back: a fire pit, cabana, and fenced outdoor space. The basement lounge has a pullout queen, Fire TV, and laundry. You're under a mile from Eastport's restaurants, 1.3 miles from Downtown Annapolis, and 2.3 miles from USNA. Pet-friendly. Free parking under the carport. Water taxi at the nearby dock.

3BR/2BA Annapolis Cottage

Our cottage is located a little over a mile from downtown Annapolis, on a quiet peninsula close to the water. It is a short car ride to the heart of downtown and we have plenty of off-street parking. The trail can be used to walk/bike downtown and to Navy Stadium. The home recently had a complete renovation with an all-new kitchen, bathrooms, and hardwood floors throughout. Enjoy a tree-lined backyard with deck and gas grill. A clean comfortable space to relax while you enjoy Annapolis.

Luxury Waterfront Annapolis/ Private Beach & Dock

Stunning Contemporary Home recently renovated on the Severn River with magnificent views of the Chesapeake Bay Bridge, a private dock & gorgeous sand beach w/ games, fire pit & hammock. Just minutes to downtown. Water views from all rooms, two propane fireplaces, designer kitchen, wine unit, electronic blackout shades, private office, screened-in porch, front patio w/grill. Master bedroom w/stand-alone tub & walk-in closet. Private road w/room for 3 cars. Spectacular Sunrises.

Charming house; walk to everywhere in Annapolis

Charming historic house, private and upscale, tucked away in the quiet President’s Hill neighborhood, located off West Street (Annapolis Arts District) with many restaurants. City Dock/Navy Stadium within walking distance. Free shuttle bus to downtown. Enjoy entire house, including front porch and back yard garden sanctuary with water pond. Peace and nature abound! House is fully stocked for cooking including all basics (spices, oil/vinegar), coffee/tea. You will feel at home here!

Independent Access Garage Apartment, Near Downtown

Independent entrance garage apartment located on the back of our house with totally independent entrance. It has a queen size bed, WIFI, 10 minute walk to Downtown. Mini kitchen with a mini-fridge, microwave, and coffee-maker. Plenty of space to store a bike. Great neighborhood with street parking available free on the weekends and two-hour limit during the week. There is free street parking during the week one block away from the apartment. Free EV charging one block away!!

Bay View Studio Apartment

Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows facing the bay, private patio, or hot tub! 50 ft of waterfront make this private walk-out garden-level apartment nestled in a small wooded oasis near downtown Annapolis a gem. Walk to the marinas or the Sailing School to catch a water taxi to downtown or book a private sail or fishing tour. Walk to Port Annapolis to get some fresh baked goods at Black Market Bakery.

1st Floor Condo in Annapolis

This newly renovated, 1st floor studio is perfectly located just across Spa Creek from historic Annapolis in Eastport. Within easy walking distance of restaurants (3 min), Main Street/City Dock (10 min) & USNA's Gate 1 entrance (14 min), our studio includes a full kitchen, high-speed wifi, free onsite parking lot, a secure building entrance, dock (limited access) and a rooftop patio (with a seasonal pool) that offers beautiful views of downtown Annapolis.

Charming, Chic Downtown Annapolis Apartment #1

In the heart of Downtown Annapolis. One block from Main Street/West Street/Church Circle. Close proximity to USNA, Ego Alley, Eastport, State House, shops, galleries, restaurants/bars and all other DTA amenities. This private apartment has an open floor plan and is elegantly decorated (with a modern twist). One Full Bathroom with tiled shower. One Bedroom with walk-in closet (with W/D).

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.

Historic Downtown in-law suite

This special place is close to everything. One block to the Naval Academy and one block to all the historic and downtown attractions. This in-law suite has a queen bed, full bath, sauna, kitchenette, seating area, and desk/dining table. Welcoming separate, quiet entrance with access to a lovely patio with seating and firepit. Twin bed can be set up and made up at guest request.