
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 3,414 ZAR per night before taxes and fees

Verified guest reviews
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)
4.91 out of 5 average rating, 475 reviews
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.
4.96 out of 5 average rating, 139 reviews
❤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!❤
4.9 out of 5 average rating, 268 reviews
Dillon Beach Surf Cottage
Our cottage is the perfect spot for singles or couples to enjoy everything about Dillon Beach. Just 100 yards from the beach with sweeping panoramic views of the Pacific Ocean and Point Reyes National Seashore. Please take a look at all the 5 Star Reviews we received this year. Our guests loved the ocean views, the location, the modern kitchen, the comfortable king size bed, and a nice bottle of wine by the fireplace or on the deck. Pet friendly so your pet can enjoy the surf and sand with you.
4.99 out of 5 average rating, 410 reviews
WiLD Vines Winery and Farm Cottage
Come enjoy our little piece of heaven centrally located between Santa Rosa and Sebastopol. Our vineyard is 10 years old and the winery is open for tasting! A vegetable garden, fruit trees and lovely back yard with fire pit provide tranquil, country ambiance. Full kitchen, large living room with big screen tv and X Box. Queen bedroom and additional small room with a crib, and a small desk. Private patio with gas bar que and hot tub. Most comfortable for a couple or family with younger children.
4.97 out of 5 average rating, 197 reviews
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
4.99 out of 5 average rating, 275 reviews
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.
4.99 out of 5 average rating, 273 reviews
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
4.95 out of 5 average rating, 860 reviews
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.
4.97 out of 5 average rating, 266 reviews
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.
4.95 out of 5 average rating, 152 reviews
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!
4.99 out of 5 average rating, 186 reviews
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.
4.84 out of 5 average rating, 353 reviewsPopular amenities for Windsor cottage rentals
Cottage rentals with a hot tub

Wine Country Historic Cottage
5.0 out of 5 average rating, 120 reviews
Calistoga Cottage • Hot Tub • Creek • Wine Country
4.87 out of 5 average rating, 167 reviews
Nestled in Nature
4.93 out of 5 average rating, 490 reviews
Riverfront Cottage w/ lush gardens & hot tub!
4.97 out of 5 average rating, 238 reviews
Luxury Cottage in Downtown Calistoga - Accessible
4.95 out of 5 average rating, 165 reviews
Riverfront w/ Dock | Hot Tub | Stunning Views
4.99 out of 5 average rating, 275 reviews
Red Door Retreat
4.92 out of 5 average rating, 391 reviews
Riverwood Cottage - Hot Tub, Direct River Access!
4.89 out of 5 average rating, 252 reviewsPet-friendly cottage rentals

Gravenstein Cottage
4.91 out of 5 average rating, 414 reviews
Creekside Retreat Cottage – Wine Country Haven
4.91 out of 5 average rating, 362 reviews
Sonoma Mountain Retreat - Jaw Dropping Views
4.97 out of 5 average rating, 530 reviews
The Atlas Calistoga - Cottage #3
4.99 out of 5 average rating, 112 reviews
Sundog - EV - Walk to Beach & Food - Fenced Yard
4.98 out of 5 average rating, 183 reviews
A Stone’s Throw: Quaint Cottage with Ocean Views
4.96 out of 5 average rating, 359 reviews
Riverside Retreat in Monte Rio
4.92 out of 5 average rating, 379 reviews
Harbor Cutie Family Friendly and Centrally Located
4.87 out of 5 average rating, 277 reviewsPrivate cottage rentals

Knix's Cabin at Salmon Creek
4.99 out of 5 average rating, 1050 reviews
Walk to the Beach, Ocean Views on Salmon Creek
4.93 out of 5 average rating, 382 reviews
Historic Garden Cottage
4.86 out of 5 average rating, 686 reviews
Sunny Riverfront Cottage
4.98 out of 5 average rating, 173 reviews
Riverfront Serenity on the Sonoma Coast
4.99 out of 5 average rating, 471 reviews
Farm Cottage With Private Pool
4.93 out of 5 average rating, 130 reviews
Historic Cuneo Cottage Downtown Sonoma
4.88 out of 5 average rating, 156 reviews
Charming Farmhouse at Stemple Creek Ranch
4.96 out of 5 average rating, 165 reviewsDestinations to explore
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