
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 $207 SGD 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)

❤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!❤

Calistoga Cottage • Hot Tub • Creek • Wine Country
Soak in the redwoods with views of gurgling creek. Perfect for romantic getaways, wine-country weekends, girls' trips, and wellness retreats. Quick Bay Area family getaway. • Hot tub among redwoods • 10 min Calistoga spas · 15 min 50+ wineries · 22 min St. Helena • 3 BR + sofa bed, sleeps 8 • Creek views · deck · grill • Kid-friendly: pack n play, 5 min to Safari West Note: accurate guest count required for county rules. Extra fees for undeclared guests. Harvest-season bookings fill fast.

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.

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.

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.

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.
Popular amenities for cottage rentals in Windsor
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

Red Door Retreat

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

Charming Cottage in Sonoma Wine Country

Dillon Beach Surf Cottage

cozy cottage in redwoods, hot tub, walk to river

Riverfront Wine Country Cottage With Views and Spa

Creekside Cottage

Riverside Retreat in Monte Rio

Sonoma Mountain Retreat - Jaw Dropping Views
Private cottage rentals

Historic Cuneo Cottage Downtown Sonoma

Charming Farmhouse at Stemple Creek Ranch

Walk to the Beach, Ocean Views on Salmon Creek

Pool & garden getaway in beautiful Sonoma Valley!

2 Beds 1.5 Bath 700 sq ft, Kitchen Laundry Desk

Andrea's Hidden Cottage

Idyllic Sonoma Vineyard Farmhouse With Pool

Wisteria Garden
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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
- Limantour Beach
- Safari West
- Point Reyes National Seashore
- Armstrong Redwoods State Natural Reserve
- Sonoma Coast State Park
- V. Sattui Winery
- Iron Horse Vineyards
- Jack London State Historic Park
- Trione-Annadel State Park
- Harbin Hot Springs
- Charles M. Schulz Museum
- Healdsburg Plaza
- VJB Vineyard & Cellars
- Sonoma State University
- Ledson Winery & Vineyards
- Lawsons Landing





