What are the top rated Cottage Rentals in Upperville?

There are a lot of options in Upperville. If you plan on staying in the Upperville area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Upperville: <a href="/property/the-mill-house-in-upperville/HA-3211312169" class="class="static-page-link"">The Mill House in Upperville -</a> <a href="/property/blue-mountain-log-cabin/HA-3211768097" class="class="static-page-link"">Blue Mountain Log Cabin</a> <a href="/property/stylishly-restored-1800-s-historic-home-heart-of-virginia-hunt-wine-country/HA-3212113225" class="class="static-page-link"">Stylishly restored 1800&#39;s historic home- heart of Virginia hunt &amp; wine country!</a> <a href="/property/historic-house-in-upperville-wineries-equestrian-events-great-location/HA-3213522249" class="class="static-page-link"">Historic house in Upperville! Wineries, equestrian events, great location!</a> <a href="/property/peaceful-mountain-retreat-near-appalachian-trail-wineries-breweries-and-more/HA-3212895179" class="class="static-page-link"">Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More</a> <a href="/property/cozy-country-getaway-in-the-heart-of-upperville/HA-3213794870" class="class="static-page-link"">Cozy Country Getaway in the Heart of Upperville</a> <a href="/property/renovated-1880s-farmhouse-near-the-blue-ridge-and-sky-meadows-with-amazing-views/HA-3213797817" class="class="static-page-link"">Renovated 1880s farmhouse near the Blue Ridge and Sky Meadows with amazing views</a> <a href="/property/historic-home-nestled-in-the-heart-of-horse-and-wine-country-kids-pet-friendly/HA-3214009486" class="class="static-page-link"">Historic home nestled in the heart of horse and wine country. Kids/pet friendly!</a> <a href="/property/historic-spacious-home-in-the-heart-of-upperville-va/HA-3213752987" class="class="static-page-link"">Historic spacious home in the heart of Upperville, VA</a> <a href="/property/historical-paris-cabin-on-farm-w-fire-pit/HA-1219912039" class="class="static-page-link"">Historical Paris Cabin on Farm w/Fire Pit!</a>

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

The average cost for a cottage rental in Upperville is $322 per night. Pawleysislandvacationrental has a wide list of great cottages near Upperville that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Upperville that allow pets?

Yes, here are the top cottage rentals in Upperville that allow you to bring your pet: 18th Century Stone Cottage minutes from historic Middleburg Hunt Country cottage in Upperville! Historical cottage in the town of Paris Middleburg address - Charming Cottage with super location in country setting Blue Mountain Log Cabin Historical Paris Cabin on Farm with Fire Pit! Grand 9BR Provenance Manor Ideal for Gatherings Stylishly restored 1800's historic home- heart of Virginia hunt & wine country! <a href="/all/usa/virginia/upperville" class="class="static-page-link"">See all pet-friendly vacation rentals in Upperville on Pawleysislandvacationrental</a>

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

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

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

As of 2025, the data from Pawleysislandvacationrental shows that there are Over 9 private swimming pools or cottages with indoor pools in the Upperville area along with other great amenities.