
Pet-friendly vacation rentals in Windsor
Find and book unique pet-friendly homes on Airbnb
Quick stats about vacation rentals that are pet-friendly in Windsor

Total vacation rentals
Explore 30 vacation rentals in Windsor

Nightly prices starting at
Windsor vacation rentals start at R 801 ZAR per night before taxes and fees

Verified guest reviews
Over 1,310 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Windsor vacation rentals include wi-fi 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!
Top-rated pet-friendly home rentals in Windsor
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

Gourmet Kitchen in Wine Country w/Hot Tub + Office
There is no better way to enjoy your stay in wine country than sipping on a glass of wine in this this stunning home! The 14ft bifold door invites out to the beautiful spacious yard where you can relax at any of the 4 sitting areas nestled under a beautiful display of lights. Featuring a chef kitchen, an office, large yard for children & pets, spacious bedrooms, stunning master bath, hot tub, fire table, games & more. Just minutes from elite award winning wineries, craft breweries & restaurants

Healdsburg House - Chiquita Road
Relax with the whole family at this peaceful and private home mins to the Healdsburg Square, Montage Resort, and Dry Creek/Alexander Valley Wineries. The updated home features an open concept kitchen, two family rooms, and a sparkling hot tub on 1.5 private acres surrounded by vineyards and oak trees. Cruise your bike to town or head directly out Chiquita Road to some of the world's greatest cycling. 2.4 miles to the Montage Resort. 2.5 miles to the Healdsburg Square. Welcome to Wine Country!

Wine Country Villa Heated Pool Hot Tub Upper Level
Welcome to Brush Creek, 20-minutes from Sonoma, Napa, Russian River, Alexander, and Knight's Valleys. Our cozy villa offers 2 unique bedrooms, including a regal King Master suite and a second King bedroom. Complimentary EV charging. Healdsburg, Calistoga, and the trendy Barlow are easily accessible. Brush Creek: where comfort, luxury, and character converge for an unforgettable wine country retreat. Heated Pool (fees may apply). No one else in the property during your stay. SVR26-101

Botany House Designer Home with Hot Tub
Property is managed by Inspired in Sonoma 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 and look forward to hosting you.

Eagle's Nest Treehouse Farm Stay
Eagle's Nest Treehouse Farm Stay is a tranquil, secluded, luxurious, romantic wilderness experience in a private forest on a 400 acre working ranch. Thirty feet above the forest floor you are nestled in a gorgeous, well-appointed suite of 1,000 year old polished redwood, with bathroom and amazing copper/glass forest-view shower. Explore hiking trails through the forest and learn about ranch operations (Highland cattle, goats and ducks). See guest comments in the space description.

West End Neighborhood Cottage
ID Tax 3099 1 bedroom cottage with a victorian-style interior tucked away with a quiet, shared yard and picnic table. Enjoy staying walking distance from historic Downtown where you'll find numerous small shops, microbreweries, bars, restaurants, gardens, book stores, coffee and local events. Blocks from multiple modes of public transportation makes this location perfect if you want to venture farther and explore the diverse landscapes of Sonoma County. Quiet Hours 9PM to 7AM

Casa de Gamay - Your Home Away From Home
Casa de Gamay is your home away from home. We've strove to include all the amenities one would need. Start with a complete kitchen with a few items ready to cook for that last minute dinner. We have the spices and staples to help you create a marvelous meal. Sit down next to our gas fireplace and watch cable TV (Comcast with a voice controlled remote), DVD player, Netflix, Hulu. Charge your car in our EV station, and then sleep in a king sized bed. Doesn't get better.

Wine Country Cottage Escape
Hidden down a quiet private lane & surrounded by vineyards, you will feel worlds away from the hustle and bustle of every day life yet only be moments away from everything Santa Rosa, Healdsburg, and the Russian River have to offer. License #LIC24-0961 TOT#4924 all bookings are subject to 12% tot Max overnight guest: 6 Max on site vehicles:NA Max off site vehicles:0 Nighttime hours 9:00 pm -7 :00 pm must be observed No outdoor amplified sound of any kind allowed.

Farmhouse Villa w/ Captivating Views & Hot Tub
Experience the ultimate Wine Country escape. The property sits on 11 private acres, offering complete privacy, peaceful surroundings, and stunning 360-degree views, including the iconic Mount Helena. Ideally located near Calistoga (15 minutes) and Healdsburg (20 minutes) and surrounded by top-rated wineries. Whether you’re here for wine tasting, relaxation, or a scenic getaway, this property delivers space, comfort, and unforgettable views.

Healdsburg Garden House
Hidden gem Best Value Ideal space for reunions and bridal parties (no events) Clean, Cozy & Private House Near Healdsburg Town Square. 20% discount for self serve rental Healdsburg Kayak Company Discount code - HEALDSBURGGARDEN20 Centrally located for Sonoma county day trips… Covered redwood deck with gas grill 50” HDTVs and fast 1 GB Wi-Fi. Fully stocked kitchen w/ dishwasher. New A/C and heating. TOT #798N

Centrally Located, Modern Wine Country Estate
Conveniently located in the heart of wine country! Just minutes away from famous wineries, breweries, world class-dining, family 'Epicenter', Sonoma County Airport and downtown Santa Rosa. This home features a gorgeous, new modern kitchen, outdoor dining area under the pergola with a BBQ and fire pit, pool table, washer and dryer, free wifi and parking. Welcome home! - Sincerely, Your Wine Country Concierge.

Designer Cottage | Garden Oasis | Walk to Plaza
✓ Seamless indoor-outdoor living. ✓ Fully equipped kitchen. ✓ On-site EV charger. ✓ Lush, private garden. ✓ Comfortably accommodates 2 guests. ✓ Dedicated workspace. ✓ Just a 4-minute walk to Healdsburg Plaza. ✓ Private, architect-designed cottage for two. ✓ Comfortable Queen Bed with Hotel pressed Sheets. ✓ Close to world-class wineries and dining. ✓ Stylish retreat created especially for couples.
Popular amenities for Windsor pet-friendly home rentals
Pet-friendly house rentals

Spacious 3BD/2BA, ideal for families!

Calistoga Tejas Trails

Peaceful location, hot tub, fire pit, game room!

Wood-Haven | In Redwoods Creekside Cabin / Hot Tub

Eco Luxury Private Sanctuary / The Farmhouse Oasis

Three-Building Healdsburg Homestead with Wine Barn

Pixel Place - A Private Arcade + Outdoor Sanctuary

Wine Country Backyard Escape
Pet-friendly home rentals with a pool

Sonoma Retreat-Pool, Spa, Barn, OD Fire & Kitchen

Homestead with Pool Hot Tub and Tastings Included

Wine Country Retreat | Pool, Hot Tub + Vibes

Pacific Gardens Retreat

Casa Chiquita - Coziest in town!

Wine Country Retreat- Privacy-Spa/Pool/Games

Vineyard Haven: Pool, Hot Tub & Wine Country Charm

Private 1+ acre, Bocce, Waterfall, Free Pool Heat
Private, pet-friendly home rentals

Country Carriage House in Downtown Geyserville

Wikiup lookout retreat

Stunning Sauna Cottage Retreat on Private Vineyard

The Perch - Outdoor Clawfoot Tub

Velouria - Hot Tub, Woodstove, Redwoods.

❤The Elegant: A Healdsburg Winery Abode! Hot Tub!❤

Luxe Guest Suite in Dry Creek 5 mins From Town!

The Black Sheep - Wine Country • Hot Tub • Theater
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R 3,685 ZAR | R 4,214 ZAR | R 3,349 ZAR | R 4,086 ZAR | R 4,086 ZAR | R 4,214 ZAR | R 7,242 ZAR | R 7,611 ZAR | R 6,617 ZAR | R 5,400 ZAR | R 5,287 ZAR | R 5,047 ZAR |
| Avg. temp | 10°C | 10°C | 11°C | 11°C | 12°C | 13°C | 14°C | 14°C | 15°C | 13°C | 12°C | 10°C |
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