What are the top rated Cottage Rentals in Hillsmere?

There are a lot of options in Hillsmere. If you plan on staying in the Hillsmere area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Hillsmere: <a href="/property/directly-across-from-usna-gate-one-steps-from-the-waterfront-and-main-street/HA-321655455" class="class="static-page-link"">Directly Across from USNA Gate One &amp; Steps from the Waterfront and Main Street!</a> <a href="/property/charming-waterfront-cottage-with-private-dock-close-to-annapolis-usna/HA-3211083319" class="class="static-page-link"">Charming Waterfront Cottage with Private Dock. Close to Annapolis &amp; USNA</a> <a href="/property/stunning-waterfront-cottage-with-breathtaking-views/HA-1214176147" class="class="static-page-link"">Stunning Waterfront Cottage with Breathtaking Views!</a> <a href="/property/perfect-location-in-the-heart-of-history/HA-321811296" class="class="static-page-link"">PERFECT LOCATION in the heart of history</a> <a href="/property/charming-historic-annapolis-home-with-two-off-street-parking-places/HA-3211050793" class="class="static-page-link"">Charming Historic Annapolis Home With Two Off-street Parking Places!</a> <a href="/property/renovated-apt-in-historic-dist-w-2-parking-spots/HA-3211355581" class="class="static-page-link"">Renovated Apt In Historic Dist w 2 Parking Spots</a> <a href="/property/the-yellow-cottage-on-harness-creek/HA-321300511" class="class="static-page-link"">The Yellow Cottage on Harness Creek</a> <a href="/property/upscale-home-with-parking-for-4-cars-in-driveway-walk-to-downtown/HA-321129519" class="class="static-page-link"">Upscale home with parking for 4 cars in driveway. Walk to downtown.</a> <a href="/property/your-annapolis-adventure-starts-here/HA-3211776700" class="class="static-page-link"">Your Annapolis Adventure Starts Here!</a> <a href="/property/historic-downtown-charmer-water-views-and-parking/HA-321693991" class="class="static-page-link"">Historic Downtown Charmer, Water Views and Parking!</a>

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

The average cost for a cottage rental in Hillsmere is $700 per night. Unpluggedweekend has a wide list of great cottages near Hillsmere that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Hillsmere that allow pets?

Yes, here are the top cottage rentals in Hillsmere that allow you to bring your pet: Walk to everything! Downtown Historic Annapolis “Arts District” PERFECT LOCATION in the heart of history 3BR Dog-Friendly Retreat with Fireplace and Patio Inn at Horn Point Charming Historic Annapolis Home With Two Off-street Parking Places! <a href="/all/usa/maryland/annapolis/hillsmere" class="class="static-page-link"">See all pet-friendly vacation rentals in Hillsmere on Unpluggedweekend</a>

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

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

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

As of 2026, the data from Unpluggedweekend shows that there are Over 1 private swimming pools or cottages with indoor pools in the Hillsmere area along with other great amenities.

Hillsmere Cottage Rentals By Owner

Walk to everything! Downtown Historic Annapolis “Arts District”

From US $700

10.0 (5 Reviews)

Cottage

Walk to everything! Downtown Historic Annapolis “Arts District”

Air Conditioner
Pet Friendly
Balcony/Terrace

Hillsmere Cottage Rentals & Holiday Homes

Find the best cottages in Hillsmere - We found 1 exact matches

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