Holiday rentals near Annapolis Landing Marina

We found 1,146 holiday rentals — enter your dates for availability

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August 2025

September 2025

Discover a selection of private holiday rentals near Annapolis Landing Marina that provide the perfect home base for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the amenities that you need and want for your stay, which might include Wi-Fi and a washer and dryer. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Annapolis Landing Marina

Showing deals for:7 Nov - 14 Nov

Welcome to Bay Ridge - a 4-bedroom and 4.5-bath luxury home in Eastport - 1-mile to downtown

Exceptional

(8 reviews)

Brand New Spacious Luxury Home

Annapolis, MD

7% off

£701 per night

includes taxes & fees

A great spot to soak in the views of the Chesapeake Bay.

Exceptional

(10 reviews)

Modern Waterfront House with amazing views of the Chesapeake Bay and a dock!

North Beach, MD

15% off

£454 per night

includes taxes & fees

Exceptional

(29 reviews)

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

Annapolis, MD

11% off

£344 per night

includes taxes & fees

Exceptional

(11 reviews)

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville, MD

16% off

£200 per night

includes taxes & fees

Kent Island Beach House:Winter, Spring, Summer & Fall there is something for All

Exceptional

(75 reviews)

Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.

Stevensville, MD

8% off

£724 per night

includes taxes & fees

Exceptional

(11 reviews)

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Tilghman, MD

9% off

£279 per night

includes taxes & fees

Exceptional

(115 reviews)

Peaceful getaway convenient to local amenities including beach, boating & food

Rock Hall, MD

8% off

£190 per night

includes taxes & fees

Koi pond, babbling brook and outdoor dining area.

Exceptional

(95 reviews)

Adjacent to Annapolis~ by beach, 25 acre park next door & TV shows filmed here!

Edgewater, MD

7% off

£387 per night

includes taxes & fees

Find spaces that suit your style

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Find the best place to stay - Annapolis Landing Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

Sleeps 11 · 3 bedrooms · 2+ bathrooms

Top rated rentals - Annapolis Landing Marina

Premier Host

A truly fabulous place for a family holiday

You won’t be disappointed – the property is in an excellent state of repair and has everything you could possibly need. The hot tub and pool were greatly enjoyed by all. Loads of glasses, cups, plates, bowls etc and every utensil you could think of. John was quick to respond to questions leading up to our arrival and was keen to ensure we were having a good time and making sure everything was OK. If this property is in your list as a potential for this area, look no further. You have found your perfect house

Clive S.

Stayed Aug 2023

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All the privacy of home
Enjoy full kitchens, pools, gardens and more
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More space, more privacy, more amenities — more value