
Cottage vacation rentals in Windsor
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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)

❤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!❤

Private Wine Country Bungalow! Sunny Treetop Views
Cozy retreat nestled in the heart of wine country. Our charming home offers a tranquil escape surrounded by breathtaking redwood trees. Relax on the 3 private decks while sipping your morning coffee or unwind in the inviting living space. The bedrooms promise a restful sleep, and the high end fully equipped kitchen allows for home-cooked meals. Conveniently near wineries, hiking, and the Russian River, our sunny forest getaway is the perfect destination for nature lovers and adventure seekers.

Rustic Beach Cottage with Hot Tub on Tomales Bay
Riley Beach Cottage sits on stilts just a few feet above the east shore of Tomales Bay. The great room, master bedroom, hot tub and northwest facing redwood decks all provide land's end views of Point Reyes National Seashore across this pristine estuary. With its own beach for launching kayaks or just doing nothing, this cottage has been a favorite due to its proximity to the water, front-row views of nature and simplicity. For more space, also book our Family Beach Cottage right next door.

Swallowtail Historic Art Studios
Antique Indonesian teakwood cottage, private deck with hot tub and very special, large, artistic bathroom/sitting room, private for cottage guests only.. Beautifully rural, yet just 6 minutes from historic downtown Petaluma and fine restaurants and shops. A short trip to the Pacific coast and the fabulous Pt. Reyes National Seashore, Tomales and Bodega Bays and towns, excellent vineyards and breweries, and San Francisco! WE FOLLOW THE CLEANING AND DISINFECTING GUIDELINES ISSUED BY AIRBNB.

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.

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

The Atlas Calistoga - Cottage #2
Make this sophisticated wine country cottage your personal Napa Valley hideaway. This luxury studio cottage on the historic Atlas estate blends a modern aesthetic with Zen-like tranquility and historic charm. This well-appointed cottage offers every comfort – from a fully stocked coffee bar to a cozy fireplace, and a sun-dappled private deck. Located in the heart of Calistoga, fine dining, shopping, spas and world-class wineries are at your doorstep!

Garden house with gas fireplace
Beautiful new cottage with lots of light, swing, and gas fireplace. Large open space with private deck looking out at Mt St. Helena. In the evening, turn on the outdoor string lights and relax on the swing under the huge oak tree before sinking into the memory foam king size bed. In the morning there is pour over coffee and robes so you can sit outside and sip your coffee. Perfect place to stay for a while, or have a romantic weekend.

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.

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

Hillside Retreat in the Redwoods w/ Hot Tub

Seaside Sanctuary • Perched Over the Bay • Dogs OK

WiLD Vines Winery and Farm Cottage

Story-Book Cottage in the Heart of Wine Country

Cottage C - Comfy and Cozy 1 bed 1 bath cottage

Riverfront Serenity on the Sonoma Coast

Riverwood Cottage - Hot Tub, Direct River Access!

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

Cute Wine Country Cottage

Cozy Sonoma Creekside Escape: Couples Retreat

Charming Cottage in Sonoma Wine Country

Cosmo Beach: Riverfront Sanctuary

cozy cottage in redwoods, hot tub, walk to river

Riverfront Wine Country Cottage With Views and Spa

Riverfront Cottage w/ lush gardens & hot tub!

Sundog - EV - Walk to Beach & Food - Yard for Dog
Private cottage rentals

Charming Farmhouse at Stemple Creek Ranch

Walk to the Beach, Ocean Views on Salmon Creek

Spring getaway in beautiful Sonoma Valley!

Knix's Cabin at Salmon Creek

Red Door Retreat

Andrea's Hidden Cottage

Sunny Riverfront Cottage

The Vintage Cottage, walkable and restful.
Quick stats about cottage rentals in Windsor

Nightly prices starting at
Windsor vacation rentals start at R2,836 ZAR per night before taxes and fees

Verified guest reviews
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!
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- Lake Berryessa
- Muir Woods National Monument
- Six Flags Discovery Kingdom
- Jenner Beach
- Bolinas Beach
- Goat Rock Beach
- Doran Beach
- Safari West
- Johnson's Beach
- Sonoma Coast State Park
- Limantour Beach
- Trione-Annadel State Park
- Chateau St. Jean
- Armstrong Redwoods State Natural Reserve
- V. Sattui Winery
- Jack London State Historic Park
- Napa Valley Wine Train Wine Shop
- Charles M. Schulz Museum
- Mount Tamalpais State Park
- Sugarloaf Ridge State Park
- Harbin Hot Springs
- Healdsburg Plaza
- St. Francis Winery and Vineyard
- VJB Vineyard & Cellars




