What are the top rated Cottage Rentals in Windsor?

There are a lot of options in Windsor. If you plan on staying in the Windsor area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Windsor: <a href="/property/cottage-home-near-the-russian-river-county-parks-numerous-wineries/HA-3212370739" class="class="static-page-link"">Cottage home near the Russian River; county parks; numerous wineries</a> <a href="/property/wine-country-retreat-large-backyard-with-pool-spa-outdoor-kitchen-fireplace/HA-3211177765" class="class="static-page-link"">Wine Country Retreat. Large backyard with pool/spa, outdoor kitchen &amp; fireplace</a> <a href="/property/flora-vina-country-home-with-vineyard-views/HA-3212549619" class="class="static-page-link"">Flora Vina - Country Home with Vineyard Views</a> <a href="/property/visit-the-russian-river-valley-in-style/HA-1214814756" class="class="static-page-link"">Visit the Russian River Valley in style!</a> <a href="/property/5bd-4ba-w-poolside-guest-house-near-healdsburg/HA-3213115202" class="class="static-page-link"">5bd/4ba w/Poolside Guest House - near Healdsburg</a> <a href="/property/modern-hilltop-healdsburg-residence-with-360-views/HA-321460814" class="class="static-page-link"">Modern Hilltop Healdsburg Residence With 360&#39; Views</a> <a href="/property/wine-country-getaway-w-fire-pit-hot-tub/HA-3212916551" class="class="static-page-link"">Wine Country Getaway W/Fire Pit &amp; Hot Tub!</a> <a href="/property/historic-queen-anne-victorian-in-the-heart-of-windsor/HA-3211638694" class="class="static-page-link"">Historic Queen Anne Victorian in the Heart of Windsor</a> <a href="/property/4-bedrooms-5-beds-3-full-bathrooms-price-depends-on-the-number-of-rented-days/HA-3212819177" class="class="static-page-link"">4 bedrooms 5 beds 3 full bathrooms - price depends on the number of rented days.</a> <a href="/property/awesome-summers-and-gorgeous-winters/HA-1214769229" class="class="static-page-link"">Awesome summers and gorgeous winters!</a>

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

The average cost for a cottage rental in Windsor is $253 per night. Ownerdirect has a wide list of great cottages near Windsor that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Windsor that allow pets?

Yes, here are the top cottage rentals in Windsor that allow you to bring your pet: Private Cottage 5 minutes from Downtown Healdsburg and Windsor on country lane Restored country home with private hot tub, amazing garden patio & firepit Spacious Cottage on Gorgeous Wine Country Estate Flora Vina - Country Home with Vineyard Views Perfect romantic getaway for two! Private retreat in the countryside. Holiday Inn Express® Windsor Sonoma Wine Country by IHG Eastside Eden Wine Tastings Included <a href="/all/usa/california/windsor" class="class="static-page-link"">See all pet-friendly vacation rentals in Windsor on Ownerdirect</a>

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

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

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

As of 2026, the data from Ownerdirect shows that there are Over 3 private swimming pools or cottages with indoor pools in the Windsor area along with other great amenities.

Windsor Cottage Rentals By Owner

Private Cottage 5 minutes from Downtown Healdsburg and Windsor on country lane

From US $123

New

Cottage

Private Cottage 5 minutes from Downtown Healdsburg and Windsor on country lane

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Owner Direct Cottages in Windsor

The Best Cottages Windsor - Plan Your Next Vacation to Windsor Today!

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