Hillsmere Shores oceanfront rentals

We found 22 oceanfront rentals — enter your dates for availability

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November 2025

December 2025

Explore Hillsmere Shores ocean view rentals

Showing deals for: 3 Feb - 6 Feb

Serene Boutique Home near Annapolis Downtown/USNA

Sleeps 8 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$781 per night

includes taxes & fees

Premier Host

Annapolis Retreat - 7 mins from downtown Annapolis!

Sleeps 9 · 5 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$914 per night

includes taxes & fees

Premier Host

Annapolis Home Near Beach & Quiet Waters Park!

Sleeps 13 · 4 bedrooms · 2+ bathrooms

for 3 nights, 1 home

AU$873 per night

includes taxes & fees

Bay Ridge house by Quiet Waters Park, Thomas Point Park

Sleeps 4 · 2 bedrooms · 1 bathroom

for 3 nights, 1 home

AU$532 per night

includes taxes & fees

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Sleeps 6 · 2 bedrooms · 1 bathroom

for 3 nights, 1 home

AU$524 per night

includes taxes & fees

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Sleeps 8 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$656 per night

includes taxes & fees

Top rated ocean view rentals - Hillsmere Shores

Premier Host

Fantastic house - clean, warm & perfectly located to get around Annapolis

Property was fully equipped with everything we needed - like a ‘home away from home’. John was extremely helpful and informative during our planning and everything was as we expected. Thanks a lot!

Simon M.

Stayed Dec 2017

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