Cottage holiday rentals in Windsor

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Top-rated cottage rentals in Windsor

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Guest favourite
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, 403 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 favourite
A charming entryway is highlighted by a bright yellow front door, featuring a diamond-patterned glass panel. Two classic black Adirondack chairs provide seating on the wooden deck, while multiple windows adjacent to the door allow natural light to fill the space.
Cottage in Guerneville
4.87 out of 5 average rating, 127 reviews

Guerneville Cabin Among the Redwoods + Wineries

- 2 min walk to the river + beach - 1 mile to downtown Guerneville - 10 min drive to wineries - 20 min drive to the Sonoma coast Surrounded by redwoods on a quaint street, this cottage is the perfect space to spend time soaking in the Russian River Valley. The home is remodeled, providing a fresh modern feel alongside traditional cottage elements, a large porch and deck. Relax in the hot tub beneath the trees, spend the day on the river, and explore surrounding wineries and breweries. Enjoy!

Guest favourite
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
4.93 out of 5 average rating, 228 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!❤

Top guest favourite
A modern living area features a high wood-beam ceiling with large windows offering lush outdoor views. A round dining table is surrounded by chairs, while a cozy seating arrangement includes a dark sofa and coffee table. A wood stove adds warmth to the space.
Cottage in Forestville
4.95 out of 5 average rating, 501 reviews

Cosmo Beach: Riverfront Sanctuary

Riverfront dog friendly 1.5 acre oasis on the Russian River. The property is private, lush, serene & sunny, with access to a huge private beach. The house is modern yet rustic & is fully equipped. It has gorgeous river valley/redwood/bridge views, decks, spa, boats, fireplace, serious kitchen, fruit trees, grapevines & wildlife. Centrally located between Healdsburg, Sebastopol & the Sonoma Coast. Fantastic wineries, trails & redwoods are minutes away. 3 beaches & river park are only steps away

Guest favourite
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, 241 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 favourite
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, 241 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.

Top guest favourite
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
4.98 out of 5 average rating, 989 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

Top guest favourite
The entrance is framed by lush greenery and manicured hedges, featuring a central fountain surrounded by blooming rose bushes. A brick pathway leads towards a welcoming wooden door, providing a tranquil outdoor setting.
Cottage in Junior College
5 out of 5 average rating, 102 reviews

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.

Top guest favourite
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, 776 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

Top guest favourite
The interior of the cottage features a spacious sleeping area with a king-sized bed, a soft sofa, and a leather love seat. A large window allows natural light, with curtains providing a touch of color. Nearby, a guitar and a small entertaining space can be seen.
Cottage in Middletown
4.98 out of 5 average rating, 168 reviews

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.

Guest favourite
A cozy bedroom is highlighted by a spacious bed adorned with a light-colored blanket and decorative pillows. Large windows allow natural light and views of the surrounding greenery, while a ceiling fan and minimalist decor enhance the room's inviting feel.
Cottage in Santa Rosa
4.91 out of 5 average rating, 150 reviews

Mins from Napa, Sonoma, spas. Cozy home w/ Hot tub

* Hot Tub to relax in, nestled among the redwoods * 3 bdrms + 1 pull-out sofa bed, sleeps 8 * 10 mins to spas in Calistoga * Wineries (5-10 mins), St. Helena(22 mins) * Gorgeous views of a gurgling creek * Backyard deck + grill * For familiies, kid friendly - pack n play, kid utensils, 5 mins to Safari West Note: accurate guest count required to honor county rules. Extra fees will be charged if more guests at check-in.

Guest favourite
A modern living area showcases a grey sofa adorned with plaid pillows. Above, three framed artworks feature intricate patterns against a navy blue wall. A wooden coffee table, centered with a vase of fresh flowers, completes the inviting space.
Cottage in Forestville
4.92 out of 5 average rating, 434 reviews

Nestled in Nature

A modern retreat in the Sonoma redwoods. The cottage is tucked away in the charming town of Forestville. Beneath the majestic redwoods, fir-covered hills, and the Russian river meandering toward Pacific shores. Forestville provides a wide variety of artisanal food, award winning restaurants and vineyards alike. An endless amount of outdoor activities from kayaking to hiking are nearly steps away.

Popular amenities for cottage rentals in Windsor

Quick stats about cottage rentals in Windsor

  • Nightly prices starting at

    Windsor holiday rentals start at $205 SGD per night before taxes and fees

  • Verified guest reviews

    Over 60 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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