Annapolis Accommodations

05/16/2025

Our commissioning week guests are going to feel some love when they arrive this weekend. Sweets and treats compliments of Bessie's Breads. www. Bessiesbreads.com. Thanks to Kristi Leigh for making this happen!

02/11/2025

🏡✨ RARELY AVAILABLE! Waterfront Getaway in Historic Downtown Annapolis – Available Only 2 Weeks a Year! ✨🌊Available for Commissioning Week!

Looking for a truly exclusive stay in the heart of Annapolis? This stunning waterfront home is a rare gem, available for rent just two weeks each year—offering an unforgettable experience for those seeking luxury, charm, and prime location.

🌅 Wake up to breathtaking waterfront views and enjoy peaceful sunrises and vibrant sunsets from this beautifully appointed retreat. Just a short stroll to the Naval Academy and City Dock, this home is perfect for Commissioning Week.

🏡 Home Highlights:
✔️ 4 spacious bedrooms, 2.5 baths – Comfortably accommodates your group
✔️ Rustic gourmet kitchen – Perfect for entertaining
✔️ Sunroom & dining area – Ideal for intimate gatherings (seats 6)
✔️ Kayaks & paddleboard included – Explore Annapolis from the water
✔️ Unparalleled waterfront access – Enjoy the best of downtown Annapolis

📅 Limited Availability – Reserve Now!
With only two rental weeks per year, this opportunity won’t last long. Contact Annapolis Accommodations today to secure your stay!

📩 Message us for more details! 🌊🏡✨

NBS23-145368 - This exclusive waterfront property is a rare gem, available for rent only two weeks each year, making it a truly unique opportunity for guests seeking a luxurious and unforgettable Annapolis experience. Located in the heart of downtown Annapolis, this stunning home offers unparalleled...

02/04/2025

Now Accepting 4- to 7-Night Stays for Commissioning Week!
Stay at The Little Lighthouse – the perfect Annapolis vacation rental just steps from the U.S. Naval Academy!

For Commissioning Week, we’re offering flexible stay options to accommodate your travel plans:

✅ 7-Night Stay (Best Value!) – $5,200 ($743 per night)
✅ 5-Night Stay – $4,100 ($820 per night)
✅ 4-Night Stay – $3,500 ($875 per night)

While we typically require a 7-night stay, we understand that not everyone can stay the full week. To offer flexibility, we are now accepting 4- or 5-night bookings at a premium rate.

Why Book The Little Lighthouse?
🏡 Unbeatable Location – Just 2 blocks from the Naval Academy & City Dock.
🚗 Private Gated Parking – Includes a secure garage for a small car/ SUV.
🛏 Spacious & Comfortable – 3 bedrooms, 2.5 baths, and modern amenities.
🌟 Easy access to downtown dining, shopping, and celebrations!

Don’t miss this opportunity to stay in one of the best-located homes in Annapolis for Commissioning Week! Limited availability – book now before it's gone!

STR21-145020 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A TEAM MEMBER WITH ADDITIONAL INSTRUCTIONS FOR BOOKING. Yes! It really is the Perfect Vacation Rental in Annapolis! Discover the perfect blend of historic charm and conte...

02/03/2025

🎓 COMMISSIONING WEEK SPECIAL– Just 1 Block from the Stadium! 🎓

Looking for the perfect home for Commissioning Week in Annapolis? Look no further! This 2BR, 2BA home in the Admiral Heights neighborhood is just 3 minutes walking distance from the Navy stadium, making it an unbeatable location for your celebration.

🏡 Recently remodeled with a stunning kitchen, hardwood floors, and a spa-like bathroom – plus an EV charging station and plenty of parking!

💥 Special Offer: Week of Commissioning Week – $2000 (plus taxes and fees) for the entire week!

📅 Availability is limited – only offered for this special event!

Why hassle with the traffic when you can walk to Graduation? Don’t miss out on this rare opportunity to stay in one of Annapolis' most sought-after locations. Single floor living and just steps to the stadium.

➡️ Send a message for more details or to book today!

NBS23-145253 EXCLUSIVE COMMISSIONING WEEK RENTAL - STEPS FROM NAVY- STADIM Please note: IF YOU REQUEST TO BOOK THIS HOME, YOU WILL BE CONTACTED BY ANNAPOLIS ACCOMMODATIONS, THE LOCAL AGENCY REPRESENTING THIS HOME, TO FINALIZE YOUR RESERVATION. Experience the excitement of Commissioning Week from the...

06/06/2024

Here's our newest property in West River - Waterfront living in a quiet community! Big front porch and a white picket fence? Birdwatching, fishing, crabbing, and boating? Yes please! Available for booking now!

STR00899 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A TEAM MEMBER WITH ADDITIONAL INSTRUCTIONS FOR BOOKING. Welcome to your dream vacation retreat! Nestled in the serene West River Community of Back Bay Beach, this coastal h...

05/03/2024

WEEKLY RATE REDUCED!!! Who is still looking for a last minute commissioning week home? Who needs a place for overflow guests? WHO WANTS TO WAVE TO ALL OF THE TRAFFIC AS YOU WALK LESS THAN 5 MINUTES TO THE STADIUM FOR GRADUATION ON FRIDAY MORNING????? We can't believe this gem is still available! CALL US!!

Coming Soon! 2 BR, 2 BA home Commissioning Week Rental - Admiral Heights neighborhood. Just a 3 min. walk to the stadium! With parking and an EV charging station! WOW! WOW! WOW! Please note: IF YOU REQUEST TO BOOK THIS HOME, YOU WILL BE CONTACTED BY ANNAPOLIS ACCOMMODATIONS, THE LOCAL AGENCY REPRESE...

05/02/2024

Could not have been a more perfect May Day in Annapolis! Congratulations to all of the winners! You still have time to come see them this weekend.

04/15/2024

WOW! JUST BECAME AVAILABLE FOR COMMISSIONING WEEK...One of our most popular properties. Please share with anyone who might be looking for a last minute rental for this very busy week in Annapolis! Call us to reserve this very special home in the heart of DTA

STR-144253 Please note: If you request to book this property, your reservation is not confirmed until you are contacted by Annapolis Accommodations to complete your booking and payment. Welcome to your Downtown Annapolis sanctuary, a historic jewel that seamlessly marries elegance with modern comfor...

04/11/2024

Do you own a rental property in or around Annapolis? Are you thinking about purchasing a home as an investment and getting into the rental game? Come learn how working with an experienced property manager can help you navigate the ever changing short and long term rental world and unlock your property's full potential.

03/19/2024

The Annapolis Spring Sailboat Show returns to the historic seaport town of Annapolis every April to showcase new and brokerage boats including catamarans, monohulls, family cruisers, daysailers, and inflatables.

03/15/2024

Wow! This great property JUST became available for Commissioning Week 2024. SOOOOO close to all the action! If you are looking for a last minute place to call home for the week, please give us a call or send us a message! Happy FriYay!

STR-143804 Charming historic house in the Heart of the Downtown Annapolis Historical District! This beautiful home, nestled along the quaint and quiet Green Street, is just 2 blocks of City Dock, restaurants, shopping, and more. Relax on the front porch with a cup of coffee or enjoy the spacious pat...