Cottage holiday rentals in Windsor

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Top-rated cottage rentals in Windsor

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Guest favourite
A wooden porch extends from the cabin, featuring a natural stone pathway and a hammock nestled between trees. The warm wood tones of the cabin contrast with the lush greenery surrounding it, creating a peaceful entrance to the retreat.
Cottage in Sebastopol
4.91 out of 5 average rating, 415 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)

Top guest favourite
A quaint entrance is framed by a wooden overhang, featuring two yellow Adirondack chairs placed on a stone patio. Nearby, potted plants sit under a blooming tree, contributing to a serene outdoor setting.
Cottage in Santa Rosa
4.97 out of 5 average rating, 185 reviews

WiLD Vines Winery and Farm Cottage

Come enjoy our little piece of heaven centrally located between Santa Rosa and Sebastopol. Our vineyard is 10 years old and the winery is open for tasting! A vegetable garden, fruit trees and lovely back yard with fire pit provide tranquil, country ambiance. Full kitchen, large living room with big screen tv and X Box. Queen bedroom and additional small room with a crib, and a small desk. Private patio with gas bar que and hot tub. Most comfortable for a couple or family with younger children.

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, 508 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

Top guest favourite
A light-filled living area features a comfortable gray sofa, accented by a textured throw and cushions. Natural wood beams and a skylight enhance the airy atmosphere. Two windows invite sunshine, while a dining area with a wooden table and four chairs is visible in the background.
Cottage in Sebastopol
4.99 out of 5 average rating, 245 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 is highlighted by large picture windows, offering views of Salmon Creek and the ocean. Cozy seating includes a circular chair and two armchairs. A wood stove stands on a wooden floor, with a decorative coffee table positioned in the center.
Cottage in Bodega Bay
4.98 out of 5 average rating, 996 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
A grand Victorian-style house features a large front porch and intricate architectural details. Lush green landscaping surrounds a central fountain, while tall trees provide shade. The combination of manicured gardens and historical charm creates an inviting outdoor space.
Cottage in Junior College
5 out of 5 average rating, 106 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, 788 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
A spacious outdoor deck is surrounded by towering redwoods, creating a serene setting. Comfortable seating arrangements include a sectional sofa with yellow cushions and a low coffee table. String lights illuminate the space, while potted plants add a touch of greenery.
Cottage in Guerneville
4.99 out of 5 average rating, 336 reviews

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!

Top guest favourite
The cottage exterior is softly illuminated by string lights, enhancing its inviting atmosphere. A bicycle hangs decoratively beside the door. Lush greenery and decorative plants are present along the pathway, leading to a porch that welcomes guests into the charming space.
Cottage in Glen Ellen
4.91 out of 5 average rating, 331 reviews

Creekside Retreat Cottage – Wine Country Haven

Wake up beside the gentle creek in your own cottage escape! •Queen bed & cozy fireplace •Peaceful waterfront deck •Fully stocked kitchen & coffee bar •Fast Wi-Fi plus workspace •Backyard with creek access Minutes to Sonoma Plaza, wineries and trails, our 800-sq-ft hideaway is perfect for couples or solo travelers seeking nature and convenience. Washer/dryer, board games and parking included. Book your Wine Country Haven today!

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
4.92 out of 5 average rating, 153 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.

Top guest favourite
Cottage in Forestville
4.93 out of 5 average rating, 441 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.

Guest favourite
A spacious outdoor deck overlooks the ocean, featuring comfortable lounge seating and a hot tub. Glass railings ensure unobstructed views of the sea and rocky coastline under a clear blue sky. Lush greenery adds a touch of nature to this relaxing space.
Cottage in Bodega Bay
4.85 out of 5 average rating, 317 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 cottage rentals in Windsor

Quick stats about cottage rentals in Windsor

  • Nightly prices starting at

    Windsor holiday rentals start at $215 SGD 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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