Smoking friendly holiday rentals in Anne Arundel County

Kone Oasis- hot tub, pool, theater/game rm.

Have fun and relax at this stylish oasis! Packed w/ amenities. Huge Pool w/multiple cabanas, HOT TUB, trampoline, playground, axe throwing, pool/ice hockey table, arcade,huge theater room and outdoor projector too, basketball court, grill, spa/library with sauna and full gym!! 5 comfy beds. Rooms split for privacy. Open kitchen/dining/living room. Cold DeerPark water fountain. Basement apt so there is some movement noise. Updated bath and an outdoor shower. 20 mins from DC & National Harbor

Pet friendly and perfect for families in Annapolis

Your family will be close to everything when you stay at this centrally located Eastport home. Less than 2 miles to the Naval Academy and downtown Annapolis. Perfect family friendly home with plenty of space to visit your midshipmen at the Naval Academy or attend a game at the Navy-Marine Corps Memorial Stadium. Close enough to walk to the waterfront to enjoy the many bars, restaurants, boat tours, or sailing excursions. We have enough space to sleep 12 and a fenced in back yard for your dog.

Chesapeake Bay Waterfront ARTectural Home w/ Pool!

JANUARY AND FEBRUARY 2026 WINTER SPECIAL. Welcome to this most relaxing home for your getaway. Perfect for vacations, retreats, meetings, anything that you can imagine. Just 4 short miles from the Bay Bridge to this 2 story home overlooking the Chesapeake Bay. Sunsets galore and constantly changing views of Ships, Sailboats, Osprey, Eagles, Heron and much more. Calm water and strong winds are all beautiful to watch from our two levels. 12' x 52' covered lower patio & enclosed upper level.

Stylish Annapolis Retreat | Personalized Gift

Every stay includes a thoughtful, personalized gift! Stylish top-floor condo located in Spa Creek outfitted with king sized beds, espresso bar, 65” 4K smart TV, Nintendo Switch, vinyl listening station, full kitchen, dedicated workplace, book nook, and covered balcony. Community perks include pool, gym, and grills. Walk to parks, courts , water & trails nearby. Just 7 mins to downtown Annapolis & the Naval Academy. Perfect for work or play—resort-style amenities and cozy comfort all in one.

Herring Bay Getaway Water view | Deale, Maryland

New, cozy, clean & comfortable water view house is perfect for a relaxing family or couples getaway! Enjoy bay breezes , bird watching, ships & sunrises from your front porch. Beautiful starry nights by the newly custom built firepit & patio! Located in a quaint waterfront neighborhood with community pier, waterfront green space and yes, amazing sunrises! Great for guests on fishing charters, day tripping, SUP, water sports, cycling and play on the Chesapeake Bay. Peloton bike upon request!

Quiet Cozy 1 Bdr Apt at BWI Airport

Furbabies Welcome! Yard Oasis! 1 Bedroom Basement suite with private entrance - 12 min. to UM Baltimore Washington Hospital -15 min to Ft. Meade - Great for military - 6 min. drive to BWI Airport terminal -10 min. drive to Casino Live - Driveway parking for 2 vehicles or RV -Wifi/Smart TV with Netflix & YT -10 min drive to Downtown Baltimore -Fully equipped kitchen - Full bathroom w/Soap/Shampoo -Late checkout available w/Fee -Doggie basket -20 miles to Annapolis, Md NO CATS permitted

Cozy Retreat in Laurel, MD!

Welcome to this comfortable, 2 bd, 2 bth 2nd floor apartment with sleeper sofa for additional guests-modern retreat in the heart of Laurel that offers the perfect blend of tranquility and convenience. You’ll have easy access to both DC and Baltimore, making it ideal for exploring the best of both cities! Inside: stocked kitchen, cozy living area with wood-burning fireplace, fast WIFI, not some, but all premium channels, and your own private balcony!

Breathtaking Waterfront North Beach Villa

Beautiful three level waterfront home. The home has been renovated recently with new exterior brick paint to modern light French grey color and new interior paint for all three floors with modern white color. The entire house has 4 large balcony decks with new paint. Home is walking distance to Herrington Harbor, Ketch 22, North Beach Boardwalk, and many more. We allow guests to use the dock for relaxing, fishing, crabbing, and kayaking.

Garden View, a spacious 1 bedroom with loft.

Relax and unwind at this peaceful and charming retreat, nestled in a quiet neighborhood. Located just minutes from Route 50, I-95, and Downtown Annapolis, Garden View is ideally situated for exploring Naval Academy sports, the Renaissance Festival, Boat Shows, and golf at The Preserve. If you prefer staying in, the fully equipped kitchen and free Wi-Fi make it easy to work or cook from the comfort of your space.

Restful pied-de-terre .

You will enjoy easy access to everything from this centrally located place. We are literally above the Nail spa and Starbucks coffee. Street parking, comfortable and clean. Ideal for traveling medical personnel and digital nomad. mid point between Baltimore and Washington DC. about an hour each way. Safely nestled on the 3rd level.

Hideaway in the Middle of Everything AYC 2+BR apt

Clean, Spacious Eastport cottage next to Annapolis Yacht Club family center, Spa Creek Bridge, and great restaurants, on Severn Ave in Eastport. City Dock and the USNA are 10-15 min walk. Wifi, 2 Queen beds, 1 pull out couch (queen). Comfortably fits 3 adult couples, or a any combination of up to 6 people.

Cozy bedroom and family room upstairs private

Very nice upstairs private suite with comfortable bed and private lounge area 5 miles from downtown Baltimore. Parking in front of the home. Beautifully decorated. the home is shared with the owners. the upstairs two rooms and half bath is for our air BNB guests only