
Cottage vacation rentals in Windsor
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Nightly prices starting at
Windsor vacation rentals start at R2,655 ZAR per night before taxes and fees

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Over 70 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)

Sonoma Mountain Incredible Views Artist's Retreat
Enjoy the perched feeling of Sonoma Mountain's setting with sweeping views and nature. The slightly tamed wilderness with an olive grove, gardens and trails sets the tone as you chill on the redwood deck. This is a studio cottage with expansive views to the western valley and Marin. Mount Tam appears through the windows. This is a beautiful unique space adjacent to a mellow artist's studio. Security gate to enter this working ranch. Well behaved and Pre-Approved dogs available for a nightly fee.

❤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!❤

Gravenstein Cottage
Nestled among the redwoods of Cazadero, Gravenstein Cottage is located in the oasis of Elim Grove, on the grounds of the award-winning Raymond's Bakery – the perfect place to unwind and enjoy Sonoma County. Decompress from the stresses of everyday life on a comfy six foot antique couch beside a real wood stove. Or refresh yourself with a hot shower under the bathroom skylight. Relax in the queen bed watching the golden varigated leaves of bamboo sway gently in the breeze outside your window.

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.

Luxury Cottage in Downtown Calistoga - Accessible
Escape to Wine Country– Your Cozy Napa Valley Retreat Tucked in charming Calistoga, our private cottages offer the perfect blend of comfort and relaxation. Enjoy luxury amenities like plush beds, fireplaces, en-suite bathroom with 2 person soaking tub, plus delightful morning treats with locally roasted coffee, pastries, and fresh fruit. Borrow a complimentary bike to explore nearby wineries or stop by our on-site office (9 AM-5PM) for wine or local tips. Pet-friendly options available.

Knix's Cabin at Salmon Creek
Our cabin has large picture windows providing views of Salmon Creek and the whitewater of the ocean. Our cabin is a cozy retreat for your getaway. Beachfront Access: A short and pleasant stroll from the cabin TOT tax ID is 1186N. Your stay supports the local community and complies with all regulations. Quiet Hours: 9:00pm to 7:00am Vacation Rental License No LIC25-0038 3075 Lucille Ave., Bodega Bay Property Owner: Lawler-Knickerbocker Certified Property Manager: Mary Lawler

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

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.

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.

Modern, Secluded Retreat - Walk to the Plaza!
Beautiful modern getaway right on Dry Creek! This secluded, peaceful property has a full kitchen, huge deck, two king bedrooms with in-suite bathrooms and a king Murphy bed and full bath in the living space. The popular Healdsburg Plaza, with all its shops and restaurants, is just a 15-minute walk away. A family of foxes often makes early morning visits and we once saw an otter in the river.
Popular amenities for Windsor cottage rentals
Cottage rentals with a hot tub

Hillside Retreat in the Redwoods w/ Hot Tub

WiLD Vines Winery and Farm Cottage

Story-Book Cottage in the Heart of Wine Country

cozy cottage in redwoods, hot tub, walk to river

Cottage C - Comfy and Cozy 1 bed 1 bath cottage

Riverfront Cottage w/ lush gardens & hot tub!

Riverfront Serenity on the Sonoma Coast

Riverwood Cottage - Hot Tub, Direct River Access!
Pet-friendly cottage rentals

Private Wine Country Bungalow! Sunny Treetop Views

Modern Cottage on Sonoma Creek

Garden house with gas fireplace

Steelhead Creek Vineyards Garden Casita

Charming Cottage in Sonoma Wine Country

Creekside Retreat Cottage – Wine Country Haven

Romantic Waterfront /Hot Tub/Fire Pit/Pet Friendly

Riverfront Wine Country Cottage With Views and Spa
Private cottage rentals

Charming Farmhouse at Stemple Creek Ranch

Walk to the Beach, Ocean Views on Salmon Creek

Spring getaway in beautiful Sonoma Valley!

2 Beds 1.5 Bath 700 sq ft, Kitchen Laundry Desk

Red Door Retreat

Andrea's Hidden Cottage

Sunny Riverfront Cottage

Wisteria Garden
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