Vacation rentals with a patio in Windsor

#1 WineCountry Retreat: Creekside Cottage

Discover creek-side wine country enchantment in our stylish oasis! A splash of modern comfort meets a darling cottage and the charm of nature. With incredible wineries, food, hiking and more nearby, you can unwind with family/friends in bright spaces, soundtrack provided courtesy of the creek. Views that inspire, vibes that relax—your perfect retreat awaits! After a day of adventure and sink into relaxation as you listen to the creek's melodic tales under a star-studded sky. Permit# ZPE15-0779

Private Wine Country Bungalow! Sunny Treetop Views

Cozy retreat nestled in the heart of wine country. Our charming home offers a tranquil escape surrounded by breathtaking redwood trees. Relax on the 3 private decks while sipping your morning coffee or unwind in the inviting living space. The bedrooms promise a restful sleep, and the high end fully equipped kitchen allows for home-cooked meals. Conveniently near wineries, hiking, and the Russian River, our sunny forest getaway is the perfect destination for nature lovers and adventure seekers.

Villa Annadel - Stunning 5 Bedroom with a Pool

Escape to your own private sanctuary at Villa Annadel. Savor the unparalleled privacy and modern sophistication of this one-of-a-kind wine country retreat. The expansive 3,200 square foot villa sits on just under 1.5 acres of privacy with a large sparkling pool, hot tub and outdoor dining gazebo. Game lovers will rejoice, from cornhole, to darts, ping pong and vintage arcade games. It’s easy to forget you are minutes from some of Santa Rosa’s finest restaurants and wine tasting destinations!

Redwood Treehouse Retreat - Hot tub, fire pit

Welcome to our Redwood Treehouse Retreat, where cozy meets luxury in the heart of nature. Nestled in the ancient trees, this romantic escape offers privacy and indulgence. Relax in the hot tub, cozy up by the fire, recharge your EV, and explore. We’re centrally located: 5 min from Occidental, 10 min to Russian River/Monte Rio beach, 20 min to coast/Sebastopol, and 30 min to Healdsburg. A perfect base to discover all the wonders of this captivating region. Your dreamy, secluded getaway awaits.

Luxury Container Home

This property will be moving to a new Airbnb listing under the same owner and host, Olivia. For reservations starting October 31, 2025 and beyond, please book through the new listing: airbnb.com/rooms/1474914649755099444 Enjoy the sounds of nature from your own private 12 acre oasis in this unique container home. Set on a private road, and built on a ridge with incredible 360-degree panoramic views from sunrise to sunset, this modern dwelling was crafted with indoor-outdoor living in mind.

Hilltop Haven 🌅 view & hot tub

Relax with the whole family at this peaceful place to stay on a quiet hilltop. This is a quaint 2 bedroom, 1 bath with a queen bed in one bedroom and bunk (twin over full) in the second bedroom. Relax in the hot tub or in the hammock on the backyard deck with a peaceful nature view or hang inside the cozy abode and make use of the fully-stocked kitchen. we have a limit of 4 overnight guests and 2 vehicles per Sonoma County permit rules. For more pictures on IG @hilltop_haven_vacation

Healdsburg 2br Cottage with Private Yard!

Relax at our renovated private guesthouse a 5 min drive (1 mi) from the Healdsburg Plaza. Updated 2 br/ 1 ba home with private yard and outdoor dining and lounge areas. Our layout is ideal for one family or friends traveling together as the one bathroom is accessed through the primary bedroom. Perfect for a wine country getaway- convenient location just outside of Healdsburg city limits in a vineyard adjacent neighborhood. We love kids and welcome them! Permit #TVR22-0119

Walk to Downtown Sebastopol * Luxe Vacation Living

Experience the epitome of luxury in our exquisite guest house. This stunning residence offers breathtaking views of the Sebastopol Laguna Preserve and the picturesque Sonoma County. Impeccably appointed, it provides everything you need for an exceptional stay. Located within walking distance of The Barlow, renowned wineries, farm-to-table restaurants, a vibrant farmers market, charming shops, and captivating galleries. It serves as the perfect base for a wine country retreat.

10-Acre Vineyard Cottage w/Hot Tub + Bocce Court

Escape to a private and peaceful retreat surrounded by Russian River Valley Chardonnay and olive trees. Set on 10 acres of producing vines, our cottage offers vineyard views, a bocce court, fire pit, garden, cruiser bikes, and a sparkling hot tub. Immerse yourself in world-class food, wine, cycling, and nature. Guests staying 3+ nights will receive a complimentary bottle of Chardonnay crafted from our vines. Your perfect wine country escape awaits!