4 Br Private Vacation Home Vacation Rental In Annapolis, Maryland

Welcome to Sing Second Stays, a comfortable and spacious retreat in the heart of Annapolis. Just 1.4 miles from Navy-Marine Corps Memorial Stadium, this home is ideal for Naval Academy families, alumni, and visitors looking to enjoy game days, Commissioning Week, I-Day, or a weekend exploring the charm of historic Annapolis.

This home holds a special place in our hearts. I’m a Naval Academy graduate (Class of 2015) and former Navy football player, and my wife, our two children, and I lived here for four years. We walked to home games, hosted friends, and made countless memories in this house before transforming it into the welcoming rental you see today. It’s our hope that guests will feel the same warmth and connection during their stay.

The location is hard to beat. We are just 2 miles from Gate 1 and 2.2 miles from Gate 8 at the United States Naval Academy. Downtown Annapolis, waterfront restaurants, historic landmarks, and boutique shopping are only minutes away. Whether you’re visiting USNA, attending a game, or simply exploring the area, this home offers unbeatable convenience.

Parking is easy and stress-free. Our U-shaped driveway provides smooth in-and-out access with space for up to four cars—two on each side—without the need to shuffle vehicles.

Inside, the home features a spacious split-foyer layout that works beautifully for families, groups, and multi-generational gatherings. The main level has an open-concept kitchen with modern appliances and all the essentials. The large living room includes ample seating and a 65-inch Sony TV, perfect for watching the game or relaxing after a day in town. The primary bedroom includes a king-sized bed, a full en-suite bathroom, and a 55-inch Samsung Smart TV. Two additional bedrooms, each with queen beds, share a second full bathroom on this floor.

Downstairs, guests enjoy a full private suite feel. There’s a bedroom with a king bed and sectional sofa, plus a large hangout room with full-over-full bunk beds, another sectional couch, and a 65-inch Vizio TV. A kitchenette includes a microwave, toaster oven, Keurig coffee maker, and mini fridge, making it easy to prep snacks or enjoy a casual breakfast. There’s also a round table ideal for dining, cards, or board games, a full bathroom, and a separate entrance. Guests will also find a washer, dryer, and utility sink on this level.

For fun and relaxation, the downstairs also includes a Pop-A-Shot basketball game, a Golden Tee arcade machine, and a variety of board games and puzzles. Whether you're traveling with kids, teens, or friends, the lower level offers a great place to unwind.

Outside, enjoy two outdoor living areas. The upper-level deck is 40 feet by 12 feet and features a dining table for six with an umbrella, an outdoor sofa, and extra seating for relaxing or dining al fresco. Below the deck, a shaded patio area provides an additional space to gather and enjoy the fresh air.

Sing Second Stays is pet-friendly because we understand that your furry companions are part of the family. We simply ask that pets are well-behaved and that guests clean up after them.

The home is equipped with high-speed Wi-Fi, three smart TVs, and all the essentials to make your stay comfortable and convenient. Guests also have access to an air mattress and two Pack 'n Plays, making it easy to accommodate additional sleepers or young children.

For your safety, the property is equipped with six exterior Eufy security cameras. These include one above the front door, two side light cameras, one covering the basement entrance, and two on the back porch. There are no cameras inside the home, and these exterior cameras are used strictly for safety and security purposes.

Here’s a quick look at the sleeping arrangements:
Upstairs includes a primary bedroom with a king bed and two bedrooms with queen beds.
Downstairs includes one king bedroom and a hangout room with full-over-full bunk beds.
An air mattress and two Pack 'n Plays are available for guest use.

The kitchen is fully stocked and includes a stovetop, oven, large refrigerator, freezer, Ninja coffee maker, blender, pots, pans, dishes, and utensils. Downstairs, the kitchenette provides added flexibility with a microwave, toaster oven, mini fridge, and Keurig coffee maker.

We ask that guests follow a few simple house rules to keep the home enjoyable for all. Smoking or vaping is not allowed inside the home or on the back deck. Please keep noise levels reasonable and be mindful of our neighbors, especially during quiet hours. No parties or unauthorized gatherings are permitted. Pets are welcome, but we ask that guests clean up after them. The fireplaces in the home are not for guest use.

Sing Second Stays was designed with comfort, convenience, and community in mind. Whether you’re returning to Annapolis for a reunion, celebrating with your midshipman, or simply exploring this beautiful historic town, we’d love to host you. We’re confident you’ll find our home to be welcoming, functional, and full of thoughtful touches that make your stay memorable.

We look forward to welcoming you to Sing Second Stays and helping you create your own Annapolis story.

Annapolis is home to this vacation home. Ballet Theater of Maryland and ARTFX Gallery of Fine Crafts and Arts are cultural highlights, and some of the area's landmarks include Chesapeake Bay Bridge and Dr. Aris T. Allen Memorial. Wild Bird Center and Maryland Hall for Creative Arts are also worth visiting.