What are the top rated Villa 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 Villa 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>

What is the rate per night for renting a villa near Winchester-on-the-Severn?

At Rentthecottages, the average rental fee for standard villas in Winchester-on-the-Severn is $275 per night. Rentthecottages has a large database of quality villas near Winchester-on-the-Severn that are suitable for families, a romantic getaway, or a solo trip with single or multiple bedrooms.

Do you have a villa in Winchester-on-the-Severn that allows pets?

Yes, here are the top villas rentals in Winchester-on-the-Severn that are pet friendly: Gaia House USNA Home Downtown Annapolis 1879 Downtown Annapolis Home with Koi Ponds and Gardens 3BR Dog-Friendly Retreat with Fireplace and Patio Flag House Inn PERFECT LOCATION in the heart of history Skyline Sanctuary See all pet-friendly vacation rentals in Winchester-on-the-Severn on Rentthecottages

Are there any rental villas in Winchester-on-the-Severn that are suitable for families?

Most of our listed villas are suitable for families. The number of rooms varies, and you can check out the complete list of villas in Winchester-on-the-Severn to find what works for you.

Do your rental villas in Winchester-on-the-Severn have indoor swimming pools?

Based on the 2026 data from our Rentthecottages site, there are more than 3 private swimming pools or villas with indoor pools in or near Winchester-on-the-Severn.

Winchester-on-the-Severn Villa Rentals【 LUXURY 】

From US $126

9.3 (53 Reviews)

Villa

Gaia House

Air Conditioner
Parking
Pet Friendly

Winchester-on-the-Severn Villa Rentals & Homes

Find villas near Winchester-on-the-Severn - We found 3 exact matches

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