Pet-friendly holiday rentals in Windsor

An airy living space is highlighted by high-beamed ceilings and large windows, allowing plenty of natural light. A gray sofa and two brown leather chairs are arranged around a round coffee table on a light-colored rug. The adjacent dining area features a wooden table, surrounded by various chairs.

5 out of 5 average rating, 114 reviews

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!

PetsOutdoor spacesKitchen

A cozy living room features two seating areas with a gray sofa and a beige armchair. A coffee table sits in front of them, and a flat-screen TV is positioned across the room, complemented by a decorative artwork and large windows allowing natural light.

4.85 out of 5 average rating, 215 reviews

Spacious 3BD/2BA, ideal for families!

Located in a quiet residential neighborhood in Santa Rosa, this spacious single level house is in the heart of California's Wine Country. With 3 bedrooms, 2 bathrooms, an open-plan living room and fully equipped kitchen there is plenty of room to cater for friends and family. The property has parking for two cars and outdoor seating to enjoy the great California weather on the new patio. Enjoy a local wine tour, explore a Giant Redwood forest or explore the stunning coastline at your feet.

WalkabilityOutdoor spacesGetting around

4.97 out of 5 average rating, 118 reviews

A modern living area features a large dark green sofa complemented by a cozy white chair and a stylish coffee table. Natural light streams through multiple windows, illuminating a patterned area rug. A dining area and kitchen are visible in the background.

Home in Calistoga

Calistoga Tejas Trails

Welcome to Tejas Trails, your country getaway nestled in Calistoga's mountain vistas, just 10 minutes from downtown. This new home (2023) is easy to share with friends or family. Enjoy refreshing mountain sunrises, dinners on the huge deck, watch sunsets sipping wine by the firepit, swing under a large oak tree, and take tranquil walks on the country road. This is the perfect place to leave the hustle and bustle behind, while still minutes from Napa Valley’s finest restaurants and wineries!

PetsOutdoor spacesView

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.

4.96 out of 5 average rating, 122 reviews

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.

Outdoor spacesWalkabilityLocation

4.93 out of 5 average rating, 646 reviews

Healdsburg Garden House

June Sale! Clean, Cozy & Private 3BR Retreat Near Healdsburg Town Square Enjoy this 3-bedroom, 2-bath home, an ideal base for Sonoma wine country. Covered redwood deck with gas grill, plus 50” HDTVs and fast 1 GB Wi-Fi. Fully stocked kitchen w/ dishwasher. New A/C and heating. 1 mile from Healdsburg Town Square, close to wineries, dining, and shops. Russian River beach nearby for outdoor activities. Perfect for families, couples, or small groups seeking a private getaway. TOT #798N

Outdoor spacesWalkabilityAccuracy

4.95 out of 5 average rating, 212 reviews

A wooden bridge connects the ground to a treehouse elevated among tall trees. The treehouse features large windows and a circular design, surrounded by lush greenery. A sturdy netting lines the sides of the walkway, ensuring safety while traversing to this unique retreat.

Treehouse in Bodega Bay

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.

PetsOutdoor spacesAccess

The exterior showcases a landscaped garden featuring diverse greenery, decorative rocks, and a serene stone pathway. A gazebo is positioned in the garden, complementing the house’s two stories, which are framed by trees and plants. The scene is illuminated by soft natural light.

4.97 out of 5 average rating, 227 reviews

Elegant & Spacious Luxury Wine Country Estate

The perfect place for your group to stay in Wine Country! Featuring two large entertaining areas and an additional dining room, this is a great place for fun and relaxation! Play ping pong, pool or poker in our game room, or dine on our spacious patio under the pergola! Relax and soak in our hot tub and enjoy the zen gardens and tranquil water feature, or sip on a glass of wine by the outdoor fire pit. Close to the Sonoma County Airport, wineries, and world-class dining. Welcome home!

Outdoor spacesWalkabilityIndoor spaces

Guest suite in Santa Rosa

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.

4.97 out of 5 average rating, 379 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.

WalkabilityOutdoor spacesAir conditioning

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.

4.94 out of 5 average rating, 113 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

PetsWalkabilityBeach

4.97 out of 5 average rating, 225 reviews

Wine Country Retreat | Pool, Hot Tub + Vibes

Summer-ready backyard + hot tub | Close to wineries Welcome to Happy House, a comfortable, clean, and welcoming home—perfect for a Sonoma County getaway any time of year. Ideal for wine tasting, visiting local breweries, hiking, mountain biking, plus weekend escapes, or remote work. 🌿 Private Backyard Large yard with pool, hot tub, and easy parking. 🍽 Fully Stocked Chef’s Kitchen 🛋 Seasonal note: Outdoor cushions/umbrellas stored late Oct–mid May. Permit # SVR25-160

Outdoor spacesWalkabilityLayout

The living room features a leather sofa and loveseat, accompanied by an end chair. A coffee table sits in the center, and a wall-mounted TV is positioned above a gas fireplace. Large windows and sliding doors provide views of the outdoor area.

4.94 out of 5 average rating, 256 reviews

Winemaker's Delight: 3BD/3BA Russian River Valley

A stylish 3-bedroom vacation rental in the heart of Santa Rosa, owned by passionate winemakers and perfectly located near top Sonoma wineries, tasting rooms, restaurants, and scenic drives. Ideal for up to six guests, this beautifully designed Wine Country retreat features inviting living spaces and three thoughtfully styled bedrooms with plush linens and serene décor, creating the perfect home base for relaxing, exploring, and enjoying the best of Sonoma County.

PetsWalkabilityComfort

A pathway leads to a welcoming front porch, flanked by greenery and blooming flowers. The light-colored home is partially shaded by surrounding trees, creating a serene approach. The yard features fresh landscaping with mulch and various plants, enhancing the inviting entrance.

4.88 out of 5 average rating, 359 reviews

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

Feel your stress melt away as you wind your way down a country road to our little piece of heaven in wine country. Our cozy home is a great starting place for your Healdsburg adventures! Private yard, super comfortable beds, well equipped kitchen, cozy living room with fireplace, free wifi and cable, game room with pool table, poker, Skee-ball plus a wonderful outdoor dining area. Just a 5 minute drive to downtown Healdsburg.

Outdoor spacesPetsQuiet

Popular amenities for Windsor pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

The kitchen features warm wooden cabinetry and an expansive central island. Stainless steel appliances include a refrigerator and microwave. Pendant lights illuminate the space, while natural light streams through a nearby window. Bar stools provide seating at the island, enhancing a functional cooking area.

5 out of 5 average rating, 192 reviews

Casa de Gamay - Your Home Away From Home

WalkabilityPetsBarbecue

4.95 out of 5 average rating, 172 reviews

An outdoor space features a plunge pool surrounded by a sun deck with lounge chairs and a sun umbrella. The home, with its wood accents, is set against a backdrop of tall redwood trees, contributing to a serene, natural setting.

Home in Occidental

Modern mid-century-inspired, Deer Ranch

PetsOutdoor spacesLayout

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.

4.95 out of 5 average rating, 691 reviews

Craftsman 2 blocks from Russian River Brewery!

PetsOutdoor spacesParking

A spacious deck features a hot tub surrounded by vibrant greenery and comfortable outdoor chairs. Views of the vineyard and rolling hills are visible in the background under a clear blue sky.

4.94 out of 5 average rating, 314 reviews

Sonoma County Historical Ranch House on a Vineyard

WalkabilityPetsSolo travel

The exterior of a beautifully designed house is presented, showcasing a light-colored facade with decorative shutters and a newly paved pathway. A stone fountain serves as a focal point amidst landscaped greenery, highlighting the inviting entrance and two stories of windows.

4.97 out of 5 average rating, 103 reviews

Wine Country Villa Heated Pool Hot Tub Upper Level

Outdoor spacesPetsComfort

4.99 out of 5 average rating, 292 reviews

The spacious outdoor deck is illuminated in the evening glow, featuring multiple seating areas, a dining table, and a hot tub. Large glass doors provide a view into the inviting interior, framed by tall redwood trees, creating a serene ambiance.

Home in Glen Ellen

Quiet Wine County Retreat with Bocce and Hot tub!

WalkabilityPetsHiking

4.94 out of 5 average rating, 170 reviews

Modern Healdsburg Retreat • Hot Tub, Bocce & Views

Outdoor spacesPetsHospitality

A private outdoor area features a hot tub adjacent to a wooden deck. A white dining table is positioned for meals, surrounded by lush greenery. Soft lighting hangs above, adding to the relaxed setting. A window on the house offers natural light to the space.

4.98 out of 5 average rating, 192 reviews

Pacific Gardens Retreat

PetsWalkabilitySleep quality

Pet-friendly home rentals with a pool

4.97 out of 5 average rating, 151 reviews

Villa in Santa Rosa

Private 1+ acre, Bocce, Waterfall, Free Pool Heat

Outdoor spacesPetsFamily

The backyard showcases a newly built pool surrounded by a spacious wood deck, featuring in-pool loungers. A picturesque sunset casts warm light on the landscape, while the home and outdoor seating areas are framed by tall trees, creating a serene country atmosphere.

4.97 out of 5 average rating, 114 reviews

Sonoma Retreat w/Pool/Spa/Barn/OD Kitchen/Orchard

PetsWalkabilityHeating

4.98 out of 5 average rating, 446 reviews

A cozy studio space features vaulted beam ceilings and warm wooden accents. A spacious bed sits against a backdrop of art, while a massage chair and a wall-mounted TV are visible. The area is complemented by decorative lighting and a welcoming atmosphere.

Guest suite in Petaluma

Petaluma Wine Country relaxing get away w/pool/spa

Outdoor spacesWalkabilityAccess

4.97 out of 5 average rating, 116 reviews

A modern kitchen features a spacious island with three woven bar stools. Hexagon-tiled walls in a soothing grey tone complement open shelving displaying dishware. Large windows allow natural light to fill the space, with greenery visible outside.

Home in Sonoma

Modern wine country stunner with pool & pickleball

PetsOutdoor spacesBathroom

4.98 out of 5 average rating, 116 reviews

Spacious 5 BR 3BA Pool EV Charger Group Getaway

WalkabilityOutdoor spacesCleanliness

4.96 out of 5 average rating, 106 reviews

Home in Kenwood

Vineyard Haven: Pool, Hot Tub & Wine Country Charm

Outdoor spacesWalkabilityLayout

The serene pool area is surrounded by lush greenery, featuring modern lounge chairs and large umbrellas for shade. The sparkling water invites relaxation, while a covered outdoor space extends from the home, providing a seamless transition to the tranquil outdoor retreat.

4.88 out of 5 average rating, 111 reviews

Serene Wine Country Retreat with Pool & Hot Tub

PetsWalkabilityBarbecue

A lively pool area is featured, showcasing a clear blue swimming pool surrounded by lounge chairs and vibrant inflatable floats. A shaded cabana provides a relaxing spot, while a nearby umbrella offers additional shade. The surrounding landscape includes lush greenery and a stone wall.

4.98 out of 5 average rating, 191 reviews

Sebastopol Gem, The Birdhouse. Hottub. Pool. Views

PetsWalkabilityLocation

Private, pet-friendly home rentals

4.94 out of 5 average rating, 300 reviews

Russian River Brewcation | Wine Country Stay

WalkabilityOutdoor spacesBeach

4.9 out of 5 average rating, 442 reviews

The exterior view of the cabin showcases a grey wooden façade, complemented by a vibrant red door. Two orange chairs are positioned on a wooden deck, surrounded by lush greenery and a decorative maple tree. Large windows allow natural light to illuminate the interior space.

Cabin in Guerneville

Velouria - Hot Tub, Woodstove, Redwoods.

PetsWalkabilityBarbecue

4.91 out of 5 average rating, 452 reviews

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

Stunning Sauna Cottage Retreat on Private Vineyard

Outdoor spacesPetsBeach

4.92 out of 5 average rating, 253 reviews

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

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

WalkabilityPetsBiking

5 out of 5 average rating, 160 reviews

A large glass door opens to a private lanai, revealing expansive views of lush vineyards and rolling hills. Comfortable seating is arranged on the deck, surrounded by greenery, while natural light enhances the serene atmosphere.

Guesthouse in Healdsburg

Luxe Guest Suite in Dry Creek 5 mins From Town!

WalkabilityOutdoor spacesHot tub

4.95 out of 5 average rating, 223 reviews

Cottage in Santa Rosa

Napa Wine Country Retreat - Villa

PetsOutdoor spacesBackyard

4.94 out of 5 average rating, 152 reviews

A spacious great room features a high wood-beamed ceiling and natural light pouring in through skylights. Comfortable lounge seating is arranged near a fireplace, with a large dining table designed to accommodate multiple guests, creating an inviting space for gatherings.

Cabin in Forestville

The Black Sheep - Wine Country • Hot Tub • Theater

Outdoor spacesWalkabilityBarbecue