Family-friendly holiday rentals in Annapolis

Villa Annapolitana • Parking 1 min • USNA 4 min

Our 1700s home offers a perfect blend of luxury and comfort. With three beautiful bedrooms, three bathrooms, and a sleek lounge area, it’s a perfect place to relax and unwind. The fully stacked kitchen is ready and waiting for you to cook a perfect meal and enjoy a glass of wine. The location is ideal, with the US Naval Academy just a 5-minute walk away. If you are looking for a peaceful escape or a fun vacation, our property has something for everyone. ✔ King Beds ✔ Smart TVs ✔ Sport Equipment

Kitchen · Family · Hospitality

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

Indoor spaces · Family · Walkability

Elegant & Authentic Annapolis

Enjoy comfortable elegance in this historic beauty on one of the prettiest streets in Downtown Annapolis--Main Street and the Water only 2 blocks away. This private unit is the full main level with its own eat-in kitchen, living room, front porch and back patio. Bedroom features queen size bed, dresser and walk-in closet. Bathroom has shower/tub and counterspace for your comfort. Street parking is available or public garage parking is a short stroll away. Relish this quiet & convenient location.

Kitchen · Indoor spaces · Check-in

Calico Cottage Guest House, king bed, free parking

Cute-as-a-bugs ear West Annapolis guest cottage just 1.5 miles from the Navy Stadium and less than 2 miles from Academy's Gate 8. Cottage features: high speed WiFi, EZ free parking, washer & dryer, kitchenette, air conditioning, self check-in and laptop friendly workspace. Park 10 feet from front door. Only 1 step to enter. No stairs to negotiate while carrying luggage! 15 min. walk to Weems Creek with scenic, serene waterviews and a few more minutes walk to popular Bean Rush Cafe.

Indoor spaces · Family · Nearby

Lil’ House - A Serene Tiny Home Experience

Newly renovated, immaculate two room tiny home. A stand-alone gem nestled against a wooded backdrop - well back from the main home - and wrapped in a huge, teak-furnished, blue stone patio with fire pit situated in a sunny opening in the mature tree canopy. Super comfy queen Murphy bed offers easy conversion of the well lit and modern main living space from living room & kitchen by day to main sleeping quarters at night. The adjoining room is a well appointed full bath and dressing area.

Family · Kitchen · Beach

Welcome Aboard!

Unique accommodations on a comfortably equipped 43 foot Hatteras yacht, just a 5 minute drive to historic downtown Annapolis and the Naval Academy. 15 minute drive to the Navy Stadium, 15 minutes drive to Rt 50. THIS LISTING IS FOR ACCOMODATIONS ONLY; BOAT MAY NOT BE DRIVEN! Forward cabin has bunk beds. Aft cabin has a queen bed. Fully equipped galley (kitchen) with 2-burner cook top, microwave/oven, fridge, toaster oven and Keurig. Boat has WIFI, heat, AC and hot water!

Kitchen · Indoor spaces · Layout

Annapolis 3 BR Sleeps 8 Waterfront Dock & Firepit

Kick back and relax in this calm, charming newly renovated coastal farmhouse waterfront two-story home with private pier/dock! Gorgeous sunrises! Experience fresh Maryland Crabs & fish caught from your private pier & enjoy the peace, serenity, bay breezes & waterfront green space! Connect to nature and explore Meredith Creek on the Chesapeake Bay by kayak or boat! Super CLEAN & new with water views from dining, living room, kitchen and bedroom! 1.5 miles to the Beach!

Kitchen · Indoor spaces · Biking

Annapolis Garden Suite

Welcome to our oasis, tucked away on a forested residential street. ~7 minutes from the Annapolis Towne Centre, ~15m from the coast, and ~30m from Baltimore and DC. Tl;dr: This is a ground-level guest suite. Inside, you’ll find 3 beds, 2 bedrooms, 1 desk, 1 kitchen with a dishwasher, oven, Nespresso/pour over, 2 TVs, a laundry room, fast wifi, a pool, patio and a forest view. We live on the top floor (separated by stairs and a locked door; separate entrances).

Indoor spaces · Kitchen · Location

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.

Indoor spaces · Family · Nearby

Weems Creek Cottage, Annapolis Waterfront

(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early. The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch. We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.

Kitchen · Indoor spaces · TV

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).

Indoor spaces · Kitchen · Getting around

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.

Family · Kitchen · TV