
Cottage vacation rentals in Windsor
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Quick stats about cottage rentals in Windsor

Nightly prices starting at
Windsor vacation rentals start at R 3,382 ZAR per night before taxes and fees

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Over 80 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Windsor rentals

4.8 Average rating
Windsor stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated cottage rentals in Windsor
Guests agree: these cottages are highly rated for location, cleanliness, and more.

Stunning Sauna Cottage Retreat on Private Vineyard
Welcome to our private, renovated, personal spa in the woods. Including a large wood-burning Finnish sauna, it features a picturesque deck with hot/cold plunge over breathtaking untouched forest with fire pit vineyard-side. This all-cedar cottage is nested below Halleck Vineyard, one of Sonoma County’s prestigious wineries. A perfect retreat, you are centrally located for the best Sonoma has to offer Sonoma County Wine Tastings (0-20 mins) Bodega Bay (20 mins) Armstrong Giant Redwoods (30 mins)
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Cosmo Beach Riverfront Sanctuary
Dog friendly 1.5 acre oasis on Russian River’s Cosmo Beach. The property is private, lush, serene & sunny, adjacent to a huge private beach. The house is modern yet artistically rustic. It has gorgeous views of the river, redwoods, bridge & sky. It also has decks, spa, boats, fireplace, serious kitchen, fruit trees, grapevines & wildlife. Centrally located between Healdsburg, Sebastopol & Sonoma Coast. Top wineries, trails & redwoods are minutes away. 3 beaches & a river park are only steps away
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❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤
❤New! Welcome to the "The Elegant Barn", our newly built stylish Barn Cottage in the HEART of wine country! Our *INSTAWORTHY* barn cottage boasts a HOT TUB, panoramic vineyard VIEWS, comfy furnishings & convertible glass indoor/outdoor doors to bring the outdoors inside! LOCATION, LOCATION, LOCATION! Set on a historic vineyard property on Dry Creek Road, the location of Healdsburg's most famous wineries, and an easy walk, bike ride or drive to many of the best wineries in the area! PETS OK!❤
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Calistoga Cottage • Hot Tub • Creek • Wine Country
Soak in the redwoods with views of gurgling creek. Perfect for romantic getaways, wine-country weekends, girls' trips, and wellness retreats. Quick Bay Area family getaway. • Hot tub among redwoods • 10 min Calistoga spas · 15 min 50+ wineries · 22 min St. Helena • 3 BR + sofa bed, sleeps 8 • Creek views · deck · grill • Kid-friendly: pack n play, 5 min to Safari West Note: accurate guest count required for county rules. Extra fees for undeclared guests. Harvest-season bookings fill fast.
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Pool & garden getaway in beautiful Sonoma Valley!
Escape to your home-away-from-home on a private residential compound: the perfect getaway spot in the heart of beautiful Sonoma Valley! 🏡 Why You’ll Love It: ✔️ Minutes to 25+ wineries & great restaurants ✔️ Easy drives to Sonoma, Calistoga, Healdsburg, Napa & the Coast ✔️ Great hiking in nearby parks ✔️ Birdwatching in the garden ✔️ Saltwater pool & bocce court ✔️ Stunning Mountain views ✔️ Private patio with gas grill & outdoor dining ✔️ Full kitchen, separate bedroom with ensuite bath
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Designer Wine Country Cottage in Perfect Location
Welcome to your wine country home, with every detail carefully designed to be the perfect luxury retreat. A 2 bed, 1 bath, 800 sq ft cottage on a private half acre garden. Walking distance to two tasting rooms, a sunny cafe, late-night gastropub, and nature trail. A ten minute drive to 18 more tasting rooms. 25 minutes to the coast. With a fully-stocked kitchen, outdoor barbecue, visiting chickens, and luxury linens and towels, this is the perfect base to explore the best of wine country.
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Wine Country Historic Cottage
The moment you step in, you will sense the calm, relaxing feeling this gem has to offer. Experience the warmth and love that has gone into every detail with the renovation. Enjoy the hot tub and a BBQ dinner in the private backyard. Sit on the front porch and enjoy the beauty of the neighborhood and the sound of the fountain. The cottage is central to all that Sonoma County has to offer. For your convenience, Pacific Market and Deli and several restaurants are blocks away.
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The Perch - Outdoor Clawfoot Tub
Overlooking a fern grotto and redwood valley, The Perch lets you experience nature up close. Come unwind and luxuriate in nature. Limited cell service. The room INSIDE has a bed, toilet, sink, mini-fridge, microwave, and electric hot water kettle. OUTSIDE a claw foot tub/shower, private deck & outside kitchen with a gas burner stove. Very rural. We live full-time on the property, and there are communal and private areas for guests. TOT#3345N, Permit#:THR18-0032
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Wine Country Farmhouse with Hot Tub
Cozy Wine Country Farmhouse: Hot Tub, Fireplace & Views Escape to a serene 3-bedroom farmhouse in Sonoma wine country! Perfect for families and friends, this pet-friendly retreat features a hot tub, fireplace, and a private fenced garden. Surrounded by oaks and an heirloom orchard, it offers rustic elegance with modern comforts like high-speed internet and an EV charger. Enjoy easy access to both Sonoma and Napa wineries for an unforgettable getaway.
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Country Carriage House in Downtown Geyserville
Linger over coffee on your quaint patio amongst 6 acres downtown in sweet Geyserville. An industrial loft vibe with wine country bones—the cottage is modern/rustic meets country-correct. Immerse yourself in country life or walk to downtown Geyserville for an Aperol Spritz. Truly where design meets refuge. Goats, horses, dogs, one heifer 🐄 named Francis, and one farm cat named Leo on property. Fully fenced front yard and back patio!
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Private Cabin (w/ hot tub & sauna) close to river
The River House is far enough from the main road to be quiet and serene but is still just walking distance from the Russian River where you can float/swim all day. The house has incredibly fast wifi as well as an electric car charging port. The neighborhood has a tennis court, Pee Wee golf course, community playground, and the house is walking distance from the Rio Nido Roadhouse which offers incredible food, drinks, and live music.
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Surfscape Beach House, Beach & Ocean views
Surfscape Beach House 2 Bedroom 2 Bathroom With Secluded Beach. Welcome to our beach house for the 'Ultimate Pacific Coast Surf Experience'. Perched atop a cliff overlooking the Pacific approximately 4 miles north of Bodega Bay. The photo's will depict views from the actual property and the beautiful coastal inspired interior. You will have your own private stairs down to a sheltered, secluded beach.
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Popular amenities for Windsor cottage rentals
Cottage rentals with a hot tub

Nestled in Nature
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WiLD Vines Winery and Farm Cottage
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Swallowtail Historic Art Studios
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Riverwood Cottage - Hot Tub, Direct River Access!
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Luxury Cottage in Downtown Calistoga - Accessible
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Riverfront w/ Dock | Hot Tub | Stunning Views
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Riverfront Cottage w/ lush gardens & hot tub!
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Red Door Retreat
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Pet-friendly cottage rentals

Elim Grove Cottage
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Dillon Beach Surf Cottage
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Cozy Sonoma Creekside Escape: Couples Retreat
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Garden house with gas fireplace
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Sonoma Mountain Retreat - Jaw Dropping Views
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A Stone’s Throw: Quaint Cottage with Ocean Views
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Harbor Cutie Family Friendly and Centrally Located
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Riverside Retreat in Monte Rio
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Private cottage rentals

2 Beds 1.5 Bath 700 sq ft, Kitchen Laundry Desk
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Light and Modern - Water Views - Close to Beach
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Knix's Cabin at Salmon Creek
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Walk to the Beach, Ocean Views on Salmon Creek
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Historic Garden Cottage: Special
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Historic Cuneo Cottage Downtown Sonoma
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Idyllic Sonoma Vineyard Farmhouse With Pool
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Sunny Riverfront Cottage
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- Lake Berryessa
- Muir Woods National Monument
- Six Flags Discovery Kingdom
- Jenner Beach
- Goat Rock Beach
- Bolinas Beach
- Doran Beach
- Johnson's Beach
- Armstrong Redwoods State Natural Reserve
- Safari West
- Point Reyes National Seashore
- Limantour Beach
- Iron Horse Vineyards
- V. Sattui Winery
- Jack London State Historic Park
- Sonoma Coast State Park
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- Harbin Hot Springs
- Healdsburg Plaza
- Sugarloaf Ridge State Park
- Salt Point State Park





