Pet-friendly vacation rentals in Windsor

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Top-rated pet-friendly home rentals in Windsor

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favourite
A bright living area features a leather couch with orange cushions, complemented by a comfortable armchair. Natural light enters through large windows, illuminating a wooden coffee table stacked with magazines. A fan hangs from the ceiling, and a flat-screen TV is mounted on the wall.
Guesthouse in Sebastopol
4.93 out of 5 average rating, 813 reviews

Sun Drenched Flat

Put up the burnt-orange parasol and settle down with book on the patio while the barbecue heats up. Sitting above a garage in a serene, walkable neighborhood, this sunlit retreat's beachy cream painted paneling gives it a chilled, refined vibe. Check out all that Sebastopol has to offer at: visitsebastopolnow.come This second story house is a very desirable space, located close to town, still being set on a very beautiful street in an friendly established older neighborhood. It is nestled between other structures on the property. One being a "Tiny House" that is right next door, my home sits behind the flat. The house has a full kitchen with all the utensils and necessary cooking items, pots pans etc. Large toaster oven that will even fit your frozen pizza. There is a space in front with some Adirondack chairs and BBQ if you want to relax outside. The house has its own separate entrance off the driveway. My house is in back of the flat, I may or may not see you, but I am available for any questions at any time. You will more than likely be greeted by our white cat with orange tips (named White Boy). If he gets a chance, Charlie our very exuberant Golden Doodle will give you a warm excited welcome. Located just 1 mile from the heart of the sweet town of Sebastopol, this area is a handy stepping off point to explore nearby wineries, scenic beaches, and shopping and restaurants at redwoods. A very nice mile walk to town or a five minute drive. There is a flight of stairs that you climb to get to the Flat space, it does not have wheelchair access. There are cats on the property, but they do not go inside the flat. Our Goldendoodle is extremely friendly. The leather couch folds flat into a double bed for accommodating two more guests. Access to the bathroom is through the bedroom however. There is no dedicated parking, however the street parking directly across from the flat, just up from, but not in front of the three mailboxes is usually always open.

Top guest favourite
A pathway of wooden planks meanders through lush greenery, leading towards a studio cottage nestled among trees. The exterior of the cottage features warm earth tones, blending with the natural surroundings. Sunlight filters through the foliage, casting dappled light on the ground.
Cabin in Sebastopol
4.94 out of 5 average rating, 236 reviews

Country Studio Cottage Sanctuary

Cozy, quiet studio cottage nestled on 1/3 acre of trees and surrounded by seasonal creeks. Indoor gas fireplace and full kitchen & large spacious deck. In Sonoma Wine Country, 12 minutes to downtown gourmet restaurants, and organic coffee houses. Take gorgeous backroads to Bodega Bay and Sonoma Coast. Nestle into the warm glow of a gas fireplace or watch for deer and wildlife from the deck or living room. This is a perfect retreat space for one or two people; it is not appropriate for parties.

Top guest favourite
An inviting living area features a large black sectional sofa complemented by a wooden coffee table atop a light area rug. Natural light streams through large windows adorned with sheer curtains, illuminating traditional wood accents and hardwood floors.
Home in Santa Rosa
4.95 out of 5 average rating, 652 reviews

Craftsman 2 blocks from Russian River Brewery!

Tastefully updated craftsman w/ traditional wood accents & original hardwood floors. Perfect for a weekend getaway, or business trip, just 2 blocks from the Russian river brewery & down town there is no better location for food and an authentic wine country experience. City of SR STR requires max occupancy: 6 max add. daytime guests 3 quiet hours must be observed between 9 p.m. and 8 a.m. no outdoor amplified sound is allowed. 3 off street parking spaces, STR Permit number #SVR25-145

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, 244 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 modern kitchen features a large island with four bar stools, blending navy cabinetry with marble countertops. Bright windows illuminate the space, revealing a glimpse of the outdoor area. An elegant gold sink contrasts with stainless steel appliances and minimalist decor.
Home in Santa Rosa
4.98 out of 5 average rating, 110 reviews

Botany House Designer Home with Hot Tub

Discover your Wine Country sanctuary in this lush, design-forward Santa Rosa retreat. With a chef’s kitchen, a six-person hot tub, a fire pit, and Restoration Hardware furnishings, every detail is crafted for comfort and style. Perfectly located near wineries, Michelin-star dining, and redwood adventures, it’s ideal for families or friends seeking luxury and connection. Book your escape today. We are pet-friendly. Message us on Social Media at Inspired in Sonoma for Inspiration and Tips.

Top guest favourite
A spacious private deck is seen with views overlooking the rolling hills and valleys. Comfortable green lounge chairs are positioned for relaxation. The deck features wooden railing and steps leading down, while a doorway connects to the guest suite.
Guest suite in Santa Rosa
4.96 out of 5 average rating, 362 reviews

Wikiup lookout retreat

We self-developed our rural property as a secluded retreat with dog-friendly gardens. To share our creation with you, we designed a private 2nd-floor guest suite (ok to bring your good dogs). Your suite includes secure parking, private entrance, deck, kitchen, dining, living, 3 beds (queen, double, twin), one bath & a fenced back yard. We are on a country road near Healdsburg, Windsor, Russian River, Sebastopol, Santa Rosa, Calistoga, Sonoma & Napa valleys, wineries & beaches.

Guest favourite
A well-appointed bedroom features a spacious bed with a light-colored upholstered headboard, draped in soft linens and a textured throw. Two nightstands flank the bed, each with a lamp and decorative items. Large windows allow natural light to illuminate the room, while soft curtains frame the view.
Home in Santa Rosa
4.93 out of 5 average rating, 100 reviews

Centrally Located Modern Wine Country Home

Your wine country retreat awaits you. This gorgeous home features a new modern kitchen, outdoor seating area, washer and dryer, free WiFi and parking. This home is conveniently located in the heart of wine country minutes away from Sonoma wineries, breweries, Sonoma County Airport, downtown Santa Rosa, downtown Sebastopol and great dinning. Due to COVID we clean and sanitize the house thoroughly before and after each stay. Welcome to your home away from home!! Your concierge Ana

Top guest favourite
A private backyard features a solar heated swimming pool surrounded by lounge seating and potted plants. A tiki bar is visible in the background, with palm trees providing shade in the sunlight. The space combines relaxation and outdoor living for a serene atmosphere.
Home in Graton
5 out of 5 average rating, 688 reviews

Eco Luxury Private Sanctuary / The Farmhouse Oasis

**Very Important** Please read description below and “Other things to note” at the bottom of this section before contacting us. • Adults Only • Private Sunny 1 Bedroom, 2 full bathroom 900 sq ft stand alone home • Private Backyard with Pool, Sauna, Outdoor Shower, and Outdoor Bathtub • Luxurious Modern Farmhouse Style • Created to feel like a boutique hotel experience • In the heart of wine country Sebastopol/ West Sonoma • Eco-Friendly products used • Strict cleaning protocols

Guest favourite
Home in Santa Rosa
4.94 out of 5 average rating, 211 reviews

Downtown Santa Rosa Walk to Russian River Brewery

Stylishly remodeled 3-bed, 1-bath Santa Rosa home, ideal for families or friends seeking easy Wine Country adventures. Walk to downtown restaurants, bars, and cafés, or explore nearby wineries, vineyards, Armstrong Redwoods, and scenic coastlines. Enjoy a beautifully updated kitchen, comfortable bedrooms, and inviting living spaces. Book today and make this your gateway to Sonoma’s outdoor beauty and Wine Country lifestyle. NOTE- Fireplace is not - functioning. TOT tax ID 3577.

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, 784 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 favourite
A cozy sitting room is depicted, featuring a round wooden table surrounded by two wicker chairs adorned with soft cushions. Shelves in the background hold decorative items and books, while light from a nearby window enhances the inviting atmosphere.
Guest suite in Santa Rosa
4.91 out of 5 average rating, 328 reviews

Peaceful Wine Country Retreat / PRIVATE ENTRANCE

Tax ID 2726N GUEST SUITE/PRIVATE ENTRANCE with Sitting Room, Large Private Bedroom & Bath. Includes a King size bed, Cable TV, Wi-Fi and Breakfast. Enjoy the beautiful view of the garden and rolling hills of Sonoma Valley’s Wine Country while relaxing in the fully stocked sitting room sipping on a glass of wine, tea, or coffee. In the evening, unwind on the patio that is just outside of the sitting room while sitting under the stars and majestic trees.

Top guest favourite
A hot tub is positioned on a grassy area, offering a view of rows of grapevines against a serene sunset. Colorful flowers are visible nearby, complementing the natural surroundings.
Home in Healdsburg
5 out of 5 average rating, 217 reviews

10-Acre Vineyard Cottage w/Hot Tub + Bocce Court

Escape to a private and peaceful retreat surrounded by Russian River Valley Chardonnay and olive trees. Set on 10 acres of producing vines, our cottage offers vineyard views, a bocce court, fire pit, garden, cruiser bikes, and a sparkling hot tub. Immerse yourself in world-class food, wine, cycling, and nature. Guests staying 3+ nights will receive a complimentary bottle of Chardonnay crafted from our vines. Your perfect wine country escape awaits!

Popular amenities for Windsor pet-friendly home rentals

When is the best time to visit Windsor?

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Avg. price$361 CAD$335 CAD$384 CAD$392 CAD$436 CAD$479 CAD$620 CAD$651 CAD$566 CAD$462 CAD$453 CAD$432 CAD
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Quick stats about vacation rentals that are pet-friendly in Windsor

  • Total vacation rentals

    Explore 40 vacation rentals in Windsor

  • Nightly prices starting at

    Windsor vacation rentals start at $69 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,400 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space and kid-friendly amenities

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Windsor vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windsor rentals

  • 4.9 Average rating

    Windsor stays are highly rated by guests—averaging 4.9 out of 5!

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