Holiday rentals with outdoor seating in Windsor

4.99 out of 5 average rating, 106 reviews

A covered patio is framed by wooden beams, offering a view of expansive vineyard landscapes and distant hills. Outdoor seating, including a dining table and lounge chairs, is arranged on the deck, inviting relaxation amid the tranquil scenery.

Guesthouse in Healdsburg

Bucher Vineyard Cottage

Discover the Charm of Our Vineyard Cottage! Escape to the heart of wine country with a stay at our fantastic one-bedroom cottage, nestled on the renowned Bucher Vineyard. Large room with kitchen & cozy seating area. Enjoy a restful night in a comfy queen bed surrounded by a stunning Redwood wall. Covered patio with heaters and fan. Deck with spectacular views of our vineyard & the Russian River Valley. Gas fire pit near deck. Hosts John & Diane are farmers and winery owners live on the property.

4.99 out of 5 average rating, 125 reviews

The exterior of a charming Victorian house is visible, featuring a welcoming front porch with a green door. Lush greenery and colorful plants frame the entrance, and a rustic wooden cart is placed nearby on a gravel pathway, enhancing the inviting outdoor space.

Home in Windsor

Gorgeous Victorian in the HEART of Windsor

Gorgeous renovated Queen Anne Victorian located in the heart of Windsor, CA combines quality finishes, modern convenience & vintage details. With a stylish kitchen, high ceilings, 3 beds/2 baths on a single level, HVAC & a huge lot with a Bocce Court. Walking distance to the Town Green, restaurants, wine tasting rooms and shopping. Just 3.5 miles from the Sonoma County Airport (STS), 5 miles to downtown Healdsburg, in the heart of the Russian River Valley & just 57 miles from the Golden Gate.

4.89 out of 5 average rating, 1,200 reviews

The studio cottage features a balanced layout with a queen bed highlighted by wooden furnishings. A small desk and an ergonomic chair are positioned near a wall-mounted television. Natural light illuminates the space through two windows, creating a comfortable environment.

Guesthouse in Santa Rosa

Clean Comfy Cottage Downtown

Our tree shaded studio cottage is one block from the heart of downtown. Stay just a two block walk from Russian River Brewing. This clean and quiet cottage has a full kitchen, a comfortable queen bed. I am happy to customize the space to your needs. I offer soft and firm mattresses. I use cotton blankets so that you can have any weight on your bed that you would like. You are welcome to stack seven or more blankets at a time. I will adjust my cleaning regimen to meet your preferences.

4.98 out of 5 average rating, 325 reviews

The Spyglass Treehouse is nestled among towering redwoods, showcasing a unique, curved design. A spacious deck wraps around the structure, offering views of the surrounding foliage. Natural grasses frame the foreground, enhancing the connection with the tranquil, forested environment.

Treehouse in Occidental

The Spectacular Spyglass Treehouse

Come, Experience the Extraordinary ~ Our Spyglass Treehouse awaits to immerse you in a memorable, magical experience of a lifetime. This magnificent creation by Artistree seamlessly blends artistry, sustainability, and a deep connection with the redwood forests. As you step into this architectural gem, you'll be greeted by a harmonious blend of local wood, bespoke furnishings, and wonderful amenities (king-size bed, sauna, cedar hot tub..) Come enjoy deep rest, romance, and rejuvenation!

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, 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

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.

4.98 out of 5 average rating, 109 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.

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.

4.96 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.

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.

4.93 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

5 out of 5 average rating, 688 reviews

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

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

4.97 out of 5 average rating, 651 reviews

The exterior of a rustic winery building is featured, characterized by its earthy tones and distinctive red door accents. Lush greenery and blooming purple flowers surround the structure, enhancing its natural setting. The building's design includes terracotta roofing and large windows that invite an abundance of natural light.

Farm stay in Healdsburg

Gracianna Winery Vineyard Loft - Farm Stay

Costs vary based on availability. Luxury estate loft in Gracianna Winery's vineyard on Westside Road's Miracle Mile of Pinot Noir in Healdsburg includes equipped kitchen with new gas Wolf Range. Pick up breakfast needs before arriving. Vineyard machines may work overnight with lights & disruptive noises, especially during the summer and harvest is in late August early Sept. TASTING ROOM CLOSED DECEMBER 1 - MARCH 31. LOFT AVAILABLE YEAR ROUND. TOT #3294N

4.96 out of 5 average rating, 434 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.

5 out of 5 average rating, 217 reviews

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

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 outdoor seating rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with Outdoor Seating

A spacious living area is illuminated by natural light from large windows. Plush sofas are arranged around a coffee table, while a fireplace adds warmth. A wall-mounted TV is positioned for easy viewing. A sliding door leads to an outdoor space with seating.

4.94 out of 5 average rating, 282 reviews

Russian River Brew-cation · Wine Tasting Retreat

4.97 out of 5 average rating, 202 reviews

A bright living area features a unique circular fireplace with a dark metal chimney as the focal point. Large windows allow natural light to fill the space, highlighting a wooden ceiling and floor. A cozy seating arrangement includes a modern leather chair and a wooden coffee table.

Home in Jenner

Pelican Hill House

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, 181 reviews

Casa de Gamay - Your Home Away From Home

4.96 out of 5 average rating, 291 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

4.96 out of 5 average rating, 432 reviews

A view of the open living area reveals a cozy sofa adorned with colorful cushions. A wooden dining table is situated nearby, accompanied by simple wooden chairs. A large artwork of sunflowers adds a touch of character, while a decorative coffee table holds potted plants and flowers.

Home in Sebastopol

Sebastopol Guest House

A single-story granny unit is presented with a beige exterior and a red door. Two windows flank the entrance, allowing natural light into the space. A small patio area with a table and chairs is visible to the side, surrounded by landscaping that adds privacy.

4.88 out of 5 average rating, 298 reviews

Sunshine cottage

4.89 out of 5 average rating, 405 reviews

The bedroom features a spacious bed with white linens accentuated by a decorative pillow. A ceiling fan is present, and natural light enters through a window. Artwork adorns the walls, including a map and framed prints. A small desk and a television stand complete the space.

Home in Healdsburg

Wine Country Cottage in Healdsburg

4.99 out of 5 average rating, 340 reviews

A modern living space is shown with mid-century-style furniture. A luxurious dark sofa is paired with two yellow accent chairs and a round coffee table. The open kitchen with wooden cabinetry and a breakfast bar is visible in the background, enhanced by natural light from high windows.

Home in Forestville

Somms Rest Designed Curated Peaceful

Apartment rentals with outdoor seating

4.97 out of 5 average rating, 861 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

4.96 out of 5 average rating, 938 reviews

A spacious living area features a light-colored sofa adorned with decorative pillows. Large windows allow natural light to fill the space, while a wooden dining table sits nearby. The adjacent doorway leads to an outdoor area, enhancing the connection with nature.

Apartment in Napa

Carriage House at Main Street Farmhouse!

4.97 out of 5 average rating, 486 reviews

A round table with two chairs is positioned on lush green grass, overlooking a misty landscape at sunrise. The fog blankets the valley, enhancing views of rolling hills and distant trees. A potted plant adorns the table, creating a serene outdoor dining space.

Apartment in Penngrove

Valley View-Sonoma Mountain Terrace

4.99 out of 5 average rating, 740 reviews

A modern studio space features a spacious layout with a queen bed and a desk area. Natural light streams in through skylights and a window, highlighting the warm wood tones of the cabinetry and furniture. A cozy seating area includes a round table and an ergonomic chair.

Apartment in Sebastopol

Amy's Local BNB - walk to town **and hot tub!**

4.99 out of 5 average rating, 177 reviews

A comfortable seating area features a spacious sofa and two high-backed chairs, accompanied by a coffee table on a light rug. Natural light enters through large windows covered with woven shades, enhancing the relaxed ambiance of the space.

Apartment in Sonoma

2 bedroom Apartment with Balcony Downtown Sonoma

4.91 out of 5 average rating, 225 reviews

A covered outdoor space is framed by wooden beams and features a gravel floor. A rectangular table is surrounded by several chairs, with a bright green lounge chair visible in the background. A decorative sign reading 'HELLO WINTER' hangs on the fence.

Apartment in Santa Rosa

Sonoma County Getaway: Mins to Wineries & Downtown

4.98 out of 5 average rating, 511 reviews

A studio apartment features a queen bed with white bedding against a vibrant blue wall. A cozy seating area includes two armchairs and a coffee table. Decorative accents are present, with a sliding barn door leading to a stylish bathroom visible in the background.

Apartment in Petaluma

Central charming studio w/pvt patio + breakfast

4.97 out of 5 average rating, 351 reviews

The exterior of a Victorian home is surrounded by vibrant greenery, featuring a white picket fence and colorful shrubs. A pathway leads to the entrance, with large windows adorning the house, highlighting its charming architectural details.

Apartment in Petaluma

Victorian Garden Apartment - Petaluma’s West Side

Condo rentals with outdoor seating

4.99 out of 5 average rating, 100 reviews

A private patio features a swinging egg chair, capable of seating at least two people, surrounded by lush bamboo and a grassy area. Outdoor lights can be seen, complementing the serene atmosphere, while a pyramid heater provides warmth for cooler evenings.

Condo in Napa

Spacious&PeacefulOasis!Beautiful!PerfectlyLocated!

The outdoor pool area features a circular pool surrounded by a spacious deck. Several lounge chairs are positioned around the pool, offering seating options. A large tree provides shade nearby, and a building with patio seating is visible in the background.

Windsor, CA, Studio Z #2

A circular outdoor pool is framed by a mixture of lounge chairs and shaded areas, surrounded by greenery and resort buildings. The water reflects a serene sky with pastel hues, inviting relaxation and leisure.

Windsor, CA, 1-Bedrm SN #1

An inviting outdoor pool is centered within a spacious courtyard, surrounded by lounge chairs and shaded umbrellas. Lush greenery lines the perimeter, and the sky features soft hues of pink and blue as the sun begins to set.

Windsor, CA, 3-Bedrm Dlx #1

A spacious pool area features a large, clear water swimming pool surrounded by lounge chairs and umbrellas. The adjacent building showcases multiple balconies and staircases, enhancing the inviting atmosphere of the resort.

1 BR Worldmark Windsor Resort Condo Wine Country

Windsor, CA, 2-Bdr Queen Z #1

An outdoor pool is surrounded by lounge chairs and shaded areas, with a large tree providing a natural focal point. The pool's calm water reflects the soft colors of the sky at dusk, creating a serene atmosphere.

Windsor, CA, 3-Bedroom #1