Holiday houses in Annapolis Yacht Basin

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Top-rated holiday rentals in Annapolis Yacht Basin

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Top Guest favourite

The exterior of a charming historic building features a welcoming front porch adorned with seating. Lush green trees and blooming flowers enhance the inviting atmosphere. American flags are displayed, highlighting the traditional character of the neighborhood.

Home in Annapolis

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.

FamilyLocationBackyard

4.99 out of 5 average rating, 160 reviews

Top Guest favourite

A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.

Cottage in Annapolis

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.

FamilyLocationAccuracy

4.97 out of 5 average rating, 473 reviews

Top Guest favourite

Cottage in Annapolis

Charming City Retreat. Walk-harbor, eateries.USNA

🌜Vintage meets Modern! As many others over the past decade, you will enjoy the year-round charm & convenience of this cottage. 🌟Walk to shops, restaurants, pubs. Free parking. 🌟Secluded patio oasis, a chimnea & cozy blankets- think s'mores! 🌟Cornhole boards add fun. 🌟Vintage outdoor soaking tub to relax. 🌟Furnishings from Robert Redford's Sundance. 🌟 Modern appliances, ceiling fans, bathrooms with ADA-height toilets. 🌟 Original pine floors. USNA Avail '29 '30 Com Wk. 6-night min.

ValueFamilyTV

4.87 out of 5 average rating, 118 reviews

Top Guest favourite

Boat in Annapolis

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!

FamilyValueSleep quality

4.97 out of 5 average rating, 116 reviews

Top Guest favourite

Condo in Annapolis

Captains Quarters | Waterfront & Pool

Welcome to Captains Quarters — your waterfront home in the Yacht Club Condominiums. Fall asleep to the sound of the water, wake up to views of Spa Creek, and walk to Eastport's best restaurants in minutes. Relax on the covered patio, swim in the community pool, or stroll across the Eastport Bridge to Downtown Annapolis. Two bedrooms, a full kitchen with Keurig and bean grinder, cable TV, and 2 free parking spots. Everything you need for an Annapolis stay on the water.

LocationFamilyCleanliness

4.98 out of 5 average rating, 124 reviews

Top Guest favourite

A serene waterfront view is captured, featuring lush green grass leading to a private patio area with a hot tub. In the background, a rainbow arches over the water, framed by a cloudy sky. The cozy apartment stands nearby, enhancing the tranquil setting.

Guest suite in Annapolis

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.

LocationValueParking

4.97 out of 5 average rating, 100 reviews

Top Guest favourite

A living area features a gray couch adorned with decorative pillows against a light wall. A recliner is positioned nearby, and a wall-mounted Smart TV is visible. A dresser with a plant sits below the TV. Natural light streams in through nearby windows.

Condo in Annapolis

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.

LocationFamilyComfort

4.96 out of 5 average rating, 180 reviews

Top Guest favourite

Guesthouse in Annapolis

Coastal Waterfront 1 Bedroom Cottage

Enjoy a peaceful waterfront getaway just 2 miles from Historic Downtown Annapolis and the U.S. Naval Academy. Located directly on the South River in a quiet neighborhood, this charming cottage features a full kitchen, 1 bedroom, washer/dryer, and sleeper sofa for up to 4 guests. Relax on the private patio with outdoor seating, grill, and fire pit, or enjoy the beautiful river views. Perfect for exploring Annapolis or simply unwinding by the water.

ValueFamilySleep quality

5.0 out of 5 average rating, 226 reviews

Top Guest favourite

The front exterior of the home features vibrant, blooming flowerbeds with a variety of blue and pink flowers. Two hanging planters with yellow flowers adorn the entryway, while a charming red door stands out against the yellow walls. A small seating area with dark chairs is visible on the porch.

Home in Annapolis

Historic & sunny home steps from USNA/downtown

This beautiful and cozy 3-bedroom, 2.5 bath home built in 1900 is located on Prince George Street, one block from Annapolis City Dock and Gate 1 (main gate) of the US Naval Academy. Filled with sunlit, spacious rooms and equipped with numerous amenities (incl. gas fireplace), this home can sleep up to 8 (on 4 beds in the 3 bedrooms and 1 futon in a private room in the basement) and offers a combination of location and charm that is hard to beat!

LocationValueBreakfast

5.0 out of 5 average rating, 205 reviews

Top Guest favourite

Cottage in Annapolis

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.

FamilyValueNearby

4.98 out of 5 average rating, 168 reviews

Top Guest favourite

Apartment in 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).

ValueLocationLayout

4.9 out of 5 average rating, 126 reviews

Top Guest favourite

Home in Annapolis

Sailing Off Gloucester

Welcome to Sailing Off Gloucester, a newly renovated historic home in downtown Annapolis, just one block from Main Street. Owned by a Naval Academy graduate and local residents, the home captures the spirit of Annapolis with coastal charm and modern luxury. This home is family-friendly and perfect for Naval Academy events, visiting Midshipmen, boat shows, and Annapolis’ many festivals!

LocationFamilyCondition

5.0 out of 5 average rating, 21 reviews