
Cottage holiday rentals in Windsor
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Quick stats about cottage rentals in Windsor

Nightly prices starting at
Windsor holiday rentals start at £120 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)

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!❤

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.

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.

Hillside Retreat in the Redwoods w/ Hot Tub
Rascal's Flat is a luxurious hillside retreat w/ hot tub in the heart of the Russian River Valley. There is a cozy 900 sq-ft, 1-bedroom, 1.5 bath cottage with a detached extra bedroom just up the hill. The cottage includes all modern amenities you could want for a comfortable stay. Outside beneath the towering Redwoods, you’ll find multiple outdoor spaces for dining, entertainment, exercise & relaxation. Experience Russian River living at its best!

Sonoma Mountain Retreat - Jaw Dropping Views
The views here are the reason people book—and guests often say they’re even more breathtaking in person. Perched atop Sonoma Mountain on 10 private acres, this peaceful retreat overlooks vineyards, olive trees, rolling hills, Mt. Tamalpais, and the distant ocean horizon. Quiet yet central to Sonoma County wine country, the cottage blends artistic warmth, outdoor living, and a uniquely creative ranch atmosphere.

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.

Story-Book Cottage in the Heart of Wine Country
This sophisticated cottage in the heart of Wine Country offers a luxury experience for those seeking the best that Sonoma County has to offer. Built in 1934 and fully updated to suit modern travelers, this property has a gourmet kitchen with an 8-burner Viking stove, wine fridge, dining room, 2 bedrooms, 2 bathrooms, indoor fireplace, outdoor hot tub and large exterior deck.
Popular amenities for cottage rentals in Windsor
Cottage rentals with a hot tub

WiLD Vines Winery and Farm Cottage

Red Door Retreat

Idyllic Sonoma Vineyard Farmhouse With Pool

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!

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

Private Wine Country Bungalow! Sunny Treetop Views

Garden house with gas fireplace

Steelhead Creek Vineyards Garden Casita

Charming Cottage in Sonoma Wine Country

Creekside Retreat Cottage – Wine Country Haven

cozy cottage in redwoods, hot tub, walk to river

Riverfront Wine Country Cottage With Views and Spa

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

Walk to the Beach, Ocean Views on Salmon Creek

Pool & garden getaway in beautiful Sonoma Valley!

Knix's Cabin at Salmon Creek

Andrea's Hidden Cottage

Sunny Riverfront Cottage

Wisteria Garden

Sonoma Vineyard Cottage - welcome to wine country!

Rustic Studio Cottage on Organic Cattle Ranch
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- Muir Woods National Monument
- Lake Berryessa
- Six Flags Discovery Kingdom
- Jenner Beach
- Bolinas Beach
- Goat Rock Beach
- Doran Beach
- Johnson's Beach
- Safari West
- Limantour Beach
- Armstrong Redwoods State Natural Reserve
- Sonoma Coast State Park
- Point Reyes National Seashore
- V. Sattui Winery
- Iron Horse Vineyards
- Trione-Annadel State Park
- Jack London State Historic Park
- Harbin Hot Springs
- Charles M. Schulz Museum
- Healdsburg Plaza
- Sonoma State University
- VJB Vineyard & Cellars
- Ledson Winery & Vineyards
- Sugarloaf Ridge State Park





