
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)
FamilyValueBackyard

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.
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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!❤
LocationValueIndoor spaces

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.
ValueLocationAccess

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.
ValueFamilySolo travel

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
ValueFamilyPool

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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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
FamilyLocationSleep quality

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.
LocationFamilyHot tub

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.
FamilyValueParking

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!
LocationValueIndoor spaces

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.
ValueFamilyCondition
Popular amenities for Windsor cottage rentals
Cottage rentals with a hot tub

Wine Country Historic Cottage
FamilyLocationWalkability

Calistoga Cottage • Hot Tub • Creek • Wine Country
ValueFamilyHospitality

Nestled in Nature
ValueFamilyAir conditioning

Riverfront Cottage w/ lush gardens & hot tub!
FamilyLocationGetting around

Luxury Cottage in Downtown Calistoga - Accessible
FamilyValueBiking

Riverfront w/ Dock | Hot Tub | Stunning Views
LocationFamilyHiking

Red Door Retreat
LocationFamilyRiver

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

Gravenstein Cottage
LocationFamilyTV

Creekside Retreat Cottage – Wine Country Haven
LocationValueWifi

Sonoma Mountain Retreat - Jaw Dropping Views
ValueLocationLaundry

The Atlas Calistoga - Cottage #3
LocationFamilyQuiet

Sundog - EV - Walk to Beach & Food - Fenced Yard
LocationFamilyAmenities

A Stone’s Throw: Quaint Cottage with Ocean Views
ValueLocationBeach

Riverside Retreat in Monte Rio
ValueFamilyEV charging

Harbor Cutie Family Friendly and Centrally Located
LocationFamilyIndoor spaces
Private cottage rentals

Knix's Cabin at Salmon Creek
FamilyValueCondition

Walk to the Beach, Ocean Views on Salmon Creek
FamilyLocationHiking

Historic Garden Cottage
ValueFamilyAir conditioning

Sunny Riverfront Cottage
ValueFamilyCleanliness

Riverfront Serenity on the Sonoma Coast
LocationFamilyKitchen

Farm Cottage With Private Pool
FamilyLocationLayout

Historic Cuneo Cottage Downtown Sonoma
LocationValueComfort

Charming Farmhouse at Stemple Creek Ranch
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- Lake Berryessa
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- Goat Rock Beach
- Bolinas Beach
- Doran Beach
- Johnson's Beach
- Armstrong Redwoods State Natural Reserve
- Point Reyes National Seashore
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