What are the top rated Cottage Rentals in Winchester-on-the-Severn?

There are a lot of options in Winchester-on-the-Severn. If you plan on staying in the Winchester-on-the-Severn area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Winchester-on-the-Severn: <a href="/property/annapolis-waterfront-tiny-house-in-garden-setting/HA-3211152603" class="class="static-page-link"">Annapolis waterfront &#34;tiny house&#34; in garden setting</a> <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/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/historic-downtown-charmer-water-views-and-parking/HA-321693991" class="class="static-page-link"">Historic Downtown Charmer, Water Views and Parking!</a> <a href="/property/charming-garden-row-home-easy-4-block-walk-to-the-heart-of-annapolis/HA-3211419775" class="class="static-page-link"">Charming garden row home, easy 4 block walk to the heart of Annapolis.</a> <a href="/property/craftsman-bungalow-suite-near-naval-academy-stadium-and-historic-district/HA-321701909" class="class="static-page-link"">Craftsman Bungalow Suite Near Naval Academy Stadium and Historic District</a> <a href="/property/historic-renovated-home-in-the-heart-of-downtown/HA-3211157887" class="class="static-page-link"">Historic Renovated Home in the Heart of Downtown</a> <a href="/property/96-five-star-reviews-located-in-the-city-of-annapolis-in-a-quiet-neighborhood/HA-321685047" class="class="static-page-link"">96 Five Star Reviews located in the City of Annapolis in a quiet neighborhood!</a>

How much does it cost to rent a cottage in Winchester-on-the-Severn?

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

Are there any cottages in Winchester-on-the-Severn that allow pets?

Yes, here are the top cottage rentals in Winchester-on-the-Severn that allow you to bring your pet: Walk to everything! Downtown Historic Annapolis “Arts District” 3BR Dog-Friendly Retreat with Fireplace and Patio PERFECT LOCATION in the heart of history Flag House Inn Skyline Sanctuary <a href="/all/usa/maryland/annapolis/winchester-on-the-severn" class="class="static-page-link"">See all pet-friendly vacation rentals in Winchester-on-the-Severn on Unpluggedweekend</a>

Do you have any rental cottages in Winchester-on-the-Severn that are suitable for families?

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

Are there quality cottages in Winchester-on-the-Severn 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 Winchester-on-the-Severn area along with other great amenities.

Winchester-on-the-Severn 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

Winchester-on-the-Severn Cottage Rentals & Holiday Homes

Find the best cottages in Winchester-on-the-Severn - We found 1 exact matches

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