What are the top rated Cottage Rentals in Annapolis?

There are a lot of options in Annapolis. If you plan on staying in the Annapolis area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Annapolis: <a href="/property/right-on-the-ocean-bluff-with-romance-and-luxury-when-only-the-best-will-do/HA-121995355" class="class="static-page-link"">RIGHT ON THE OCEAN BLUFF with Romance and Luxury: When ONLY THE BEST Will Do.</a> <a href="/property/come-take-in-the-ocean-gaze-at-the-starry-skies-commune-with-nature/HA-321440141" class="class="static-page-link"">Come take in the ocean, gaze at the starry skies, commune with nature.</a> <a href="/property/windsong-oceanfront-views-from-all-rooms-single-story-private-hot-tub/HA-321862948" class="class="static-page-link"">Windsong.Oceanfront Views from ALL rooms, Single Story, &amp; Private Hot Tub</a> <a href="/property/spacious-sea-ranch-home-with-great-ocean-views/HA-3211012640" class="class="static-page-link"">Spacious Sea Ranch Home With Great Ocean Views</a> <a href="/property/stunning-oceanfront-home-w-incredible-ocean-views/HA-321317390" class="class="static-page-link"">Stunning Oceanfront Home w/Incredible Ocean Views</a> <a href="/property/wake-to-whales-golf-the-coast-unwind-in-style/HA-3212556467" class="class="static-page-link"">Wake to Whales, Golf the Coast, Unwind in Style</a> <a href="/property/amazing-ocean-views-relaxing-home-surrounded-by-nature/HA-3212230442" class="class="static-page-link"">Amazing ocean views, relaxing home surrounded by nature.</a> <a href="/property/kid-friendly-ocean-views-private-and-quiet/HA-3211118065" class="class="static-page-link"">Kid-friendly, ocean views, private and quiet</a> <a href="/property/friends-and-family-will-love-staying-at-tranquility-base-in-the-sea-ranch/HA-3211742822" class="class="static-page-link"">Friends and family will love staying at Tranquility Base in the Sea Ranch</a> <a href="/property/wine-country-retreat-with-pool-sauna-ocean-views-near-beach-dog-friendly/HA-3213836817" class="class="static-page-link"">Wine country retreat with pool, sauna, &amp; ocean views - near beach - dog-friendly</a>

How much does it cost to rent a cottage in Annapolis?

The average cost for a cottage rental in Annapolis is $349 per night. Cartagenacaribbeantours has a wide list of great cottages near Annapolis that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Annapolis that allow pets?

Yes, here are the top cottage rentals in Annapolis that allow you to bring your pet: Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge! Clemons' Cottage Chic and Modern Loft Home in Desirable Sea Ranch! Walk to the Beach and Trails Blue Sky, light-filled cottage on the hillside Come take in the ocean, gaze at the starry skies, commune with nature. Hines House The Sea Ranch Lodge Sunny Home. Hot Tub. Walk to 2 Beaches, Rec Center, Bluff Trail and the Lodge. <a href="/all/usa/california/cazadero/annapolis" class="class="static-page-link"">See all pet-friendly vacation rentals in Annapolis on Cartagenacaribbeantours</a>

Do you have any rental cottages in Annapolis that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Annapolis to find one that works for you.

Are there quality cottages in Annapolis that have indoor swimming pools?

As of 2026, the data from Cartagenacaribbeantours shows that there are Over 4 private swimming pools or cottages with indoor pools in the Annapolis area along with other great amenities.

Annapolis Cottage Rentals By Owner

Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!

From US $377

10.0 (411 Reviews)

Cottage

Incredibly Beautiful, Private, Unique Home Perched On The Bluff At Ocean's Edge!

Parking
Pool
TV

Annapolis Cottage Rentals & Holiday Homes

Find the best cottages in Annapolis - We found 4 exact matches

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