Cottage vacation rentals in Windsor

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Top-rated cottage rentals in Windsor

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Guest favorite
An outdoor fire pit surrounded by four wooden chairs offers a welcoming gathering space. The stone patio extends outward, framed by lush greenery and the vibrant hues of sunset. A vineyard is visible in the background, enhancing the natural setting.
Cottage in Sebastopol
4.91 out of 5 average rating, 423 reviews

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)

Guest favorite
The exterior of the barn cottage is featured, showcasing a two-story structure with large windows illuminated in a warm glow. The entrance is adorned with wooden doors and a star accent. A spacious deck is visible above, providing an inviting outdoor space.
Cottage in Healdsburg
4.92 out of 5 average rating, 241 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!❤

Guest favorite
A private hot tub is situated on a wooden deck, with views of the calm water and distant hills. Two wooden chairs are positioned nearby, inviting relaxation while enjoying the serene landscape.
Cottage in Marshall
4.92 out of 5 average rating, 249 reviews

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.

Top guest favorite
An inviting outdoor space is surrounded by lush greenery and blooming lavender. Two wooden chairs are positioned to overlook sweeping views of the valley and vineyards below. A stone fire pit adds to the serene atmosphere of this natural setting.
Cottage in Penngrove
4.97 out of 5 average rating, 485 reviews

Sonoma Mountain Incredible Views Artist's Retreat

Enjoy the perched feeling of Sonoma Mountain's setting with sweeping views and nature. The slightly tamed wilderness with an olive orchard and gardens sets the tone as you chill on the redwood deck. This is a studio cottage with expansive views to the western valley and Marin. Mount Tam appears through the windows from your super comfy bed. This is a beautiful unique space adjacent to a mellow artist's studio. The kitchen isNOTE: Well behaved and Pre-Approved dogs available for a nightly fee.

Guest favorite
A charming wooden cottage, featuring a peaked roof and decorative carved details, is surrounded by lush greenery. The private deck showcases vibrant potted plants, enhancing the natural setting. Sunlight filters through the leaves, casting a warm glow on the rustic structure.
Cottage in Petaluma
4.84 out of 5 average rating, 982 reviews

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.

Top guest favorite
A bright and welcoming living space features a mix of modern and cozy elements. Wooden beams enhance the ceiling above various seating arrangements, including a plush sofa and a round dining table. Natural light filters through large windows, highlighting framed art on the walls.
Cottage in Sebastopol
4.99 out of 5 average rating, 249 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.

Guest favorite
A charming cottage exterior is framed by lush greenery and mature trees. The white facade is complemented by light blue shutters and a dark front door, while two wicker chairs are placed on a semi-private porch, inviting relaxation among the serene environment.
Cottage in Calistoga
4.95 out of 5 average rating, 119 reviews

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.

Top guest favorite
A spacious living area features a gray sofa adorned with plush pillows, complemented by a round accent chair. Natural light fills the room through large windows, highlighting a wooden coffee table with a decorative piece. Wooden beams create an inviting ambiance.
Cottage in Bodega Bay
4.99 out of 5 average rating, 1,000 reviews

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

Guest favorite
Cottage in Santa Rosa
4.97 out of 5 average rating, 246 reviews

Alpine Ranch Farmhouse ~ Wine Country

Cozy Wine Country Farmhouse: Hot Tub, Fireplace & Views Escape to a serene retreat in the heart of wine country, surrounded by majestic oaks and a small orchard. Unwind in the hot tub beneath a canopy of stars. Inside, enjoy the airy ambiance created by abundant natural light, blending the outdoors with the comforts of home. Located near countless Sonoma and Napa vineyards, this idyllic farmhouse offers the perfect blend of tranquility and proximity to wine country adventures.

Top guest favorite
A charming cottage features a well-maintained front yard adorned with lush greenery and colorful flowers. The inviting exterior showcases a mix of brick and stucco, with multiple arching doorways and windows, set against a tranquil evening sky.
Cottage in Junior College
4.98 out of 5 average rating, 110 reviews

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. Please note, an additional 14% City of Santa Rosa tax will be collected prior to check-in.

Top guest favorite
An outdoor deck surrounded by lush greenery features a fire pit at its center, surrounded by seating options. A claw foot tub is positioned against the railing, while a small round table and folding chairs provide additional seating. Bright green cushions add color to the wooden lounge chairs.
Cottage in Occidental
4.94 out of 5 average rating, 793 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

Guest favorite
A spacious outdoor seating area features a comfortable sofa with plush cushions facing the ocean. The scene captures the soothing waves and rugged coastline, complemented by a fire feature at the center, all under a beautiful sky transitioning from day to evening.
Cottage in Bodega Bay
4.85 out of 5 average rating, 322 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.

Popular amenities for Windsor cottage rentals

Quick stats about cottage rentals in Windsor

  • Nightly prices starting at

    Windsor vacation rentals start at R2,870 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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