What are the top rated Cottage Rentals in Winston?

There are a lot of options in Winston. If you plan on staying in the Winston area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Winston: <a href="/property/an-urban-oasis-in-downtown-winston-salem/HA-3211234505" class="class="static-page-link"">An urban oasis in downtown Winston-Salem</a> <a href="/property/winston-salem-s-man-cave/HA-321919886" class="class="static-page-link"">Winston-Salem&#39;s Man Cave</a> <a href="/property/walking-distance-to-reynolda-house-and-gardens-close-to-wake-forest-university/HA-321769049" class="class="static-page-link"">Walking distance to Reynolda House and Gardens. Close to Wake Forest University</a> <a href="/property/majestic-getaway-cabin-near-wake-forest-university/HA-1214443819" class="class="static-page-link"">Majestic Getaway Cabin near Wake Forest University</a> <a href="/property/elegant-pet-friendly-ranch-home-close-to-everything/HA-3211494991" class="class="static-page-link"">Elegant Pet Friendly Ranch Home close to everything!</a> <a href="/property/outrageous-house-in-the-woods/HA-321511151" class="class="static-page-link"">Outrageous House In The Woods</a> <a href="/property/serene-5bd-4ba-sleeps-12-5-min-to-wake-forest-univ/HA-3213168401" class="class="static-page-link"">Serene 5Bd/4Ba - sleeps 12+ - 5 min to Wake Forest Univ</a> <a href="/property/the-vista-studio-close-to-downtown-wake-forest-baptist-hospital/HA-3212695689" class="class="static-page-link"">The Vista Studio-Close to Downtown Wake Forest Baptist Hospital</a> <a href="/property/quiet-newly-renovated-near-everything/HA-3213462636" class="class="static-page-link"">Quiet, newly renovated. Near everything!</a> <a href="/property/convenient-to-i-40-dt-wake-forest-uncsa-wssu-benton-center-hospitals/HA-3211701416" class="class="static-page-link"">✨Convenient to I-40, DT, Wake Forest, UNCSA, WSSU, Benton Center, &amp; Hospitals✨</a>

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

The average cost for a cottage rental in Winston is $238 per night. Cruiseandresorts has a wide list of great cottages near Winston that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Winston that allow pets?

Yes, here are the top cottage rentals in Winston that allow you to bring your pet: 3 bedrooms close to downtown, Hospital & college Historic Beauty: 5BR Home with Yard Near Hospital Summit Street Inns The Spruce Goose- Eclectic 2BD/1.5BA ENTIRE Condo <a href="/all/usa/north-carolina/winston" class="class="static-page-link"">See all pet-friendly vacation rentals in Winston on Cruiseandresorts</a>

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

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

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

As of 2026, the data from Cruiseandresorts shows that there are Over 737 private swimming pools or cottages with indoor pools in the Winston area along with other great amenities.

Winston Cottage Rentals By Owner

3 bedrooms close to downtown, Hospital & college

From US $101

10.0 (1 Review)

House

3 bedrooms close to downtown, Hospital & college

Air Conditioner
Parking
Pet Friendly

Winston Cottage Rentals & Holiday Homes

Find the best cottages in Winston - We found 737 exact matches

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