Holiday rentals with a fireplace in Windsor

4.95 out of 5 average rating, 196 reviews

An inviting Mediterranean-style patio is filled with vibrant mosaics and potted plants. Two charming chairs surround a small table under a pergola, providing a shaded area, while lush greenery enhances the area’s privacy and tranquility.

Guesthouse in Healdsburg

Mediterranean Getaway with breakfast Healdsburg

Attractive, ultra-romantic, almost-a-cottage Bed&Breakfast(no extra charge for breakfast) is waiting for you in our restored 1930s-era home in a peaceful corner of northern Sonoma County. Ours is a quiet rural road nestled in beautiful oaks, redwoods, California bay, buckeye trees near the bottom of Fitch Mountain, some 100’ above the Russian Rive. Fitch Mountain is known for its interesting local history, eclectic building styles, beautiful views, secluded neighborhoods, and friendly spirit.

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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!

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4.93 out of 5 average rating, 217 reviews

A cozy treehouse retreat is surrounded by towering redwoods, resting on stilts above the forest floor. Large windows illuminate the structure, allowing natural light to flood the interior. A wooden deck extends outdoors, providing a relaxing space to enjoy the serene woodland environment.

Treehouse in Camp Meeker

Redwood Treehouse Retreat - Hot tub, fire pit

Welcome to our Redwood Treehouse Retreat, where cozy meets luxury in the heart of nature. Nestled in the ancient trees, this romantic escape offers privacy and indulgence. Relax in the hot tub, cozy up by the fire, recharge your EV, and explore. We’re centrally located: 5 min from Occidental, 10 min to Russian River/Monte Rio beach, 20 min to coast/Sebastopol, and 30 min to Healdsburg. A perfect base to discover all the wonders of this captivating region. Your dreamy, secluded getaway awaits.

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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.

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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!

Indoor spacesSleep qualityFamily

A light-filled living area features a sectional sofa, coffee table, and a flat-screen television mounted on the wall. Large windows provide sweeping views of the surrounding vineyards and natural light. A patterned area rug complements the wood flooring, enhancing the cozy atmosphere.

5 out of 5 average rating, 166 reviews

VINEYARD VIEW - Beautiful 3 bed/2 bath, Santa Rosa

Enjoy beautiful unobstructed vineyard views from your own private patio while sipping coffee or a glass of wine. This beautifully decorated new home is located in a quiet peaceful neighborhood in N. Santa Rosa in the heart of wine country with several wineries and breweries nearby. We are located only 5 miles from downtown Santa Rosa, 12 miles from the Healdsburg plaza, and 45 miles from Napa. This one-story home is perfect for enjoying all that Sonoma County has to offer.

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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.

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A three-story building is seen with a colorful facade displaying verdant green, red, and yellow hues, surrounded by trees. The outdoor pool area features lounge chairs along the water's edge, illuminated against a night sky. The interior image shows a kitchen with wooden cabinets and dining space.

4.87 out of 5 average rating, 196 reviews

Windsor 2 Bed/2 Bath Condo ~ Pool ~ Hot Tub ~ Gym

***Condo: 1,023 square feet 2 bedroom/2 bath- King size bed in the master bedroom, two twin beds in the 2nd bedroom (can be put together to make a king), and one queen Murphy bed in the living room. Additional amenities include a full kitchen and dining area, gas fireplace, washer and dryer and a private terrace with gas barbecue. Maximum occupancy is six. *** twin beds in 2nd bedroom can be put together to make a king size bed. Please request in advance.

Indoor spacesSleep qualityValue

4.96 out of 5 average rating, 439 reviews

A spacious living area features a blue sofa adorned with a soft orange throw. A large area rug with intricate patterns anchors the space, while natural light floods in through large windows. A wooden coffee table rests centrally, complemented by decorative items.

Home in Windsor

Winelight Vineyard Home With Spa

Gated driveway, private, scenic, safe, secure, and impeccably clean. Unwind, prepare dinner on granite counter tops in this newly remodeled well-stocked gourmet kitchen. Enjoy plush amenities, fine decor, hot tub, romantic fireplace, French doors leading to outdoor decks, secluded rural vibe, reliably fast internet. Close to Sonoma County's best wineries, breweries and restaurants. There is a guest laundry, designer carport, and ample parking for guests.

Indoor spacesSleep qualityFamily

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.

Sleep qualityIndoor spacesBeach

4.97 out of 5 average rating, 617 reviews

A rustic cabin is nestled among towering redwood trees, featuring wooden shingles and large windows. A wooden deck, adorned with string lights, enhances the inviting exterior, while the natural landscape provides a serene backdrop. A gravel path leads to the entrance.

Cabin in Occidental

Rustic Yet Luxurious Cabin in the Redwoods

This rustic yet luxurious cabin is the perfect place to unplug. Walk through the woods, relax by a fire, and enjoy the food and wine of the Russian River Valley. 10 minutes from the beach. Minutes from Occidental, Graton, Forestville, and Guerneville. House has a full bathroom, bedroom downstairs with a Cal King bed and one upstairs with two twin beds. 5 acres in the redwoods, trampoline, fire pit area, high-speed Internet.

Sleep qualityHeatingBackyard

4.97 out of 5 average rating, 247 reviews

A bright living area features a spacious white sectional couch and a wooden coffee table. An expansive bookshelf holds various items, with a television and fireplace being focal points. Large glass doors open to a garden, bringing in natural light and outdoor views.

Guesthouse in Healdsburg

Healdsburg Contemporary Cottage With Lush Backyard

Your private Healdsburg retreat—just a 4-minute walk to downtown wine tasting rooms, restaurants, shops, and the Farmers Market. This stylish guest cottage offers parking in front of a private entry, garden with al fresco dining, BBQ, lounge area, and a fully equipped Pilates studio. Designed with international contemporary art and thoughtful touches, it’s perfect for a weekend escape or a longer stay while house hunting.

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Popular amenities for Windsor Accommodation with Fireplace

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a fireplace

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

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A heated swimming pool reflects the early evening sky, surrounded by lush greenery. Comfortable lounge chairs are positioned around the pool, complemented by a shaded umbrella. The vineyard is visible in the background, enhancing the peaceful atmosphere of this outdoor space.

4.92 out of 5 average rating, 130 reviews

Vineyard Vista, Modern Farmhouse Cottage with Pool

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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!

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4.98 out of 5 average rating, 178 reviews

Wake Up in Your Own Private Vineyard - Healdsburg

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4.94 out of 5 average rating, 314 reviews

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.

Home in Sebastopol

Sonoma County Historical Ranch House on a Vineyard

HeatingIndoor spacesLong stay

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

Sleep qualityIndoor spacesAccuracy

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!

Sleep qualityIndoor spacesGetting around

The outdoor space features a gazebo with a fire pit, surrounded by comfortable seating. Lounge chairs are positioned near an unheated pool, and a dining table with seating is visible in the background, creating a welcoming atmosphere for relaxation and gatherings.

4.94 out of 5 average rating, 175 reviews

Wine Country Escape: Pool & Hot Tub. Fast WiFi

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Apartment rentals with a fireplace

4.98 out of 5 average rating, 57 reviews

A charming two-story building features a stucco exterior, adorned with a tile roof and decorative balcony. Flowering trees are visible in the foreground, contributing to the inviting streetscape. Large windows allow for ample natural light, while the storefront displays an enticing sign.

Apartment in Sonoma

Vine Alley Two by BeautifulPlaces

Indoor spacesSleep qualityCheck-in

4.97 out of 5 average rating, 882 reviews

A hand-painted welcome sign is displayed on a white oval background. Red cursive lettering spells 'Welcome,' surrounded by colorful flowers and green leaves, creating an inviting entry point.

Apartment in Santa Rosa

Private Getaway in West Santa Rosa

Sleep qualityIndoor spacesDecor

Explore Sonoma | 2BR + Pools & Relaxation

FamilyAmenitiesCleanliness

4.67 out of 5 average rating, 3 reviews

WorldMark Windsor - Wine Country 3br Condo

Location

4.98 out of 5 average rating, 526 reviews

Apartment in Petaluma

Central charming studio w/private patio

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Superhost

A large outdoor pool is surrounded by lounge chairs on a sunlit deck. Various umbrellas provide shaded seating areas, while well-maintained landscaping and the resort buildings are visible in the background under a clear blue sky.

4.9 out of 5 average rating, 10 reviews

Wine Country Sonoma Windsor 2 Bedroom Sleeps 6!

Sleep qualityHot tubNearby

4.88 out of 5 average rating, 469 reviews

A cozy living space features a brown leather sofa and a matching ottoman, with a coffee table in the center. A decorative wall art piece and a flat-screen TV are displayed nearby. A kitchen area is visible, showcasing light wood cabinetry and modern appliances.

Apartment in Sonoma

Modern Family Farm

Indoor spacesHeatingDecor

The image captures a resort exterior featuring three-story buildings with balconies overlooking a large swimming pool. Lounge chairs and umbrellas are set up around the pool area, inviting relaxation under clear blue skies.

5 out of 5 average rating, 7 reviews

Studio -Windsor WorldMark Resort

Sleep qualityIndoor spacesKitchen

Villas with a fireplace

4.96 out of 5 average rating, 196 reviews

The exterior of the villa is adorned with lush greenery and shrubs, creating a serene atmosphere. The warm-toned facade features a tiled roof and wooden shutters. A gravel driveway leads to the entrance, framed by neatly arranged garden spaces and decorative pots.

Villa in Napa

An Italian Villa in the heart of Napa Valley!

HeatingSleep qualityWalkability

4.97 out of 5 average rating, 151 reviews

Villa in Santa Rosa

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

Indoor spacesSleep qualityAir conditioning

Superhost

Villa in Occidental

4.87 out of 5 average rating, 99 reviews

Exclusive Forest Retreat, 8 private acres +Hot Tub

Sleep qualityHeatingLocation

4.92 out of 5 average rating, 53 reviews

The exterior of the lodge is surrounded by lush greenery and mature palms, highlighting a mix of natural stone and wood finishes. A stone pathway leads to an inviting entrance flanked by steps, enhancing the connection to the serene outdoor space.

Villa in Geyserville

Adventure Alexander Valley Lodge w/ Pool & Hot tub

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Luxe

Villa in Glen Ellen

4.96 out of 5 average rating, 25 reviews

Bungalow Twins

Indoor spacesFamilyGetting around

4.93 out of 5 average rating, 119 reviews

A sunlit living area features large windows, allowing natural light to fill the space. Two leather armchairs sit adjacent to a wooden coffee table, which holds a tray. A television accompanies decorative plants and warm wooden accents, creating a cozy atmosphere.

Villa in Penngrove

Charming Home in Penngrove

HeatingSleep qualityCondition

4.98 out of 5 average rating, 54 reviews

Villa in Calistoga

Mountain Villa with Hot Tub

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