Winston - Salem featuring a house, heritage elements and interior views

Winston-Salem cottages

We found 18 cottages — enter your dates for availability

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October 2025

16

November 2025

Explore Winston-Salem cottage rentals

Private kitchen

Premier Host

Upscale City Cottage Getaway

Sleeps 4 · 2 bedrooms · 1 bathroom

Exterior

Premier Host

Bright & Airy 1910 Cottage with 2 King Master Suites! Updated! Close to campus!

Sleeps 4 · 2 bedrooms · 2 bathrooms

Find spaces that suit your style

House

Condo/Apartment

Cottages in Winston-Salem

Cottages in Williamsburg Square

Holiday Rental options in Winston-Salem

Lake holiday rentals in Winston-Salem

Mountain holiday rentals in Winston-Salem

Pet-friendly holiday rentals in Winston-Salem

Monthly rentals in Winston-Salem

Holiday rentals with pool in Winston-Salem

Oceanfront holiday rentals in Winston-Salem

Beach holiday rentals in Winston-Salem

Family-friendly holiday rentals in Winston-Salem

Holiday rentals with hot tub in Winston-Salem

Ski holiday rentals in Winston-Salem

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