
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 3,357 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)

2 Beds 1.5 Bath 700 sq ft, Kitchen Laundry Desk
Experience fresh forest air, tranquility and relaxation at our unique treehouse nestled in the redwoods. Private outdoor hangout areas, private entrance, full kitchen, large bedroom with a memory foam king bed, work station with standing desk and high speed internet, laundry and 1.5 baths. A short walk to the Russian River, 1.8 miles to Armstrong Redwoods Park, 25 minute drive to the coast. The cottage is nestled on its own private level of the property while the host's house is on street level.

❤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!❤

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

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.

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.

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

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!

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.

Nestled in Nature
A modern retreat in the Sonoma redwoods. The modest cottage is tucked away in the charming town of Forestville. Beneath the majestic redwoods, fir-covered hills, and the Russian river meandering toward Pacific shores. Forestville provides a wide variety of artisanal food, award winning restaurants and vineyards alike. An endless amount of outdoor activities from kayaking to hiking are nearly steps away.

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.

Bee Haven Cottage
This unique property is located only 2.4 miles from Healdsburg Plaza. Situated on a historic 11-acre farm with 5 acres of Zinfandel grapes. This newly renovated Studio cottage was built in 1903. This creekside cottage is fully restored in an artist's handcrafted manner. All the furnishings are of the highest quality. Enjoy the natural surroundings while soaking in the private outdoor spa.
Popular amenities for Windsor cottage rentals
Cottage rentals with a hot tub

WiLD Vines Winery and Farm Cottage

Luxury Cottage in Downtown Calistoga - Accessible

Riverfront w/ Dock | Hot Tub | Stunning Views

Hillside Retreat in the Redwoods | Hot Tub

Riverwood Cottage - Hot Tub, Direct River Access!

Swallowtail Historic Art Studios

Riverfront Cottage w/ lush gardens & hot tub!

Glen Ellen Creek House/ Heart of Sonoma Valley
Pet-friendly cottage rentals

Gravenstein Cottage

Dillon Beach Surf Cottage

Cozy Sonoma Creekside Escape: Couples Retreat

Sonoma Mountain Retreat - Jaw Dropping Views

The Atlas Calistoga - Cottage #3

A Stone’s Throw: Quaint Cottage with Ocean Views

Harbor Cutie Family Friendly and Centrally Located

cozy cottage in redwoods, hot tub, walk to river
Private cottage rentals

Private cottage with amazing views

Knix's Cabin at Salmon Creek

Walk to the Beach, Ocean Views on Salmon Creek

Historic Cuneo Cottage Downtown Sonoma

Historic Garden Cottage: Special

Farm Cottage With Private Pool

Riverfront Serenity on the Sonoma Coast

Interlude Serene Sonoma
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