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Cottage vacation rentals in Healdsburg

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Top-rated cottage rentals in Healdsburg

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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

4.91 out of 5 average rating, 343 reviews

Stunning Sauna Cottage Retreat on Private Vineyard

Welcome to our private, renovated, personal spa in the woods. Including a large wood-burning Finnish sauna, it features a picturesque deck with hot/cold plunge over breathtaking untouched forest with fire pit vineyard-side. This all-cedar cottage is nested below Halleck Vineyard, one of Sonoma County’s prestigious wineries. A perfect retreat, you are centrally located for the best Sonoma has to offer Sonoma County Wine Tastings (0-20 mins) Bodega Bay (20 mins) Armstrong Giant Redwoods (30 mins)

A wooden deck features two Adirondack chairs positioned to overlook the river, accompanied by a small table. Lush greenery surrounds the area, with hills visible in the background under a clear blue sky.

Cottage in Monte Rio

4.96 out of 5 average rating, 194 reviews

Riverfront Cottage w/ lush gardens & hot tub!

Take it easy at this unique, modern, cottage w/ a hot tub located on the banks of the Russian River in historic Duncans Mills. The soulful dwelling is mid-century modern style w/ expansive decks, lush gardens, outdoor space & a serene, yet hip, interior including a cozy living room, modern kitchen, 2 bedrooms and 2 baths. The lay out is two separated bed/bath units- offering complete privacy for 2 couples or parents w/ kids! Float the river, soak in the hot tub or just relax. Pets OK- $50 fee

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

4.94 out of 5 average rating, 187 reviews

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

❤New! Welcome to the "The Elegant Barn", our newly built stylish Barn Cottage in the HEART of wine country! Our *INSTAWORTHY* barn cottage boasts a HOT TUB, panoramic vineyard VIEWS, comfy furnishings & convertible glass indoor/outdoor doors to bring the outdoors inside! LOCATION, LOCATION, LOCATION! Set on a historic vineyard property on Dry Creek Road, the location of Healdsburg's most famous wineries, and an easy walk, bike ride or drive to many of the best wineries in the area! PETS OK!❤

A modern living area features a high wood-beam ceiling with large windows offering lush outdoor views. A round dining table is surrounded by chairs, while a cozy seating arrangement includes a dark sofa and coffee table. A wood stove adds warmth to the space.

Cottage in Forestville

4.95 out of 5 average rating, 470 reviews

Cosmo Beach: Riverfront Sanctuary

Riverfront dog friendly 1.5 acre oasis on the Russian River. The property is private, lush, serene & sunny, with access to a huge private beach. The house is modern yet rustic & is fully equipped. It has gorgeous river valley/redwood/bridge views, decks, spa, boats, fireplace, serious kitchen, fruit trees, grapevines & wildlife. Centrally located between Healdsburg, Sebastopol & the Sonoma Coast. Fantastic wineries, trails & redwoods are minutes away. 3 beaches & river park are only steps away

A private hot tub is situated on a wooden deck, with views of the calm water and distant hills. Two wooden chairs are positioned nearby, inviting relaxation while enjoying the serene landscape.

Cottage in Marshall

4.93 out of 5 average rating, 212 reviews

Rustic Beach Cottage with Hot Tub on Tomales Bay

Riley Beach Cottage sits on stilts just a few feet above the east shore of Tomales Bay. The great room, master bedroom, hot tub and northwest facing redwood decks all provide land's end views of Point Reyes National Seashore across this pristine estuary. With its own beach for launching kayaks or just doing nothing, this cottage has been a favorite due to its proximity to the water, front-row views of nature and simplicity. For more space, also book our Family Beach Cottage right next door.

Top guest favorite

A serene outdoor space features a sparkling saltwater pool surrounded by lush greenery and colorful landscaping. A cozy cottage is positioned in the background, with a gray roof and welcoming entrance. Comfortable lounge chairs are arranged neatly beside the pool, inviting relaxation.

Cottage in Kenwood

4.99 out of 5 average rating, 257 reviews

Private Charming Poolside 1 BD/BA in Sonoma Valley

Escape to your home-away-from-home on a private residential compound: the perfect getaway spot in the heart of beautiful Sonoma Valley! 🏡 Why You’ll Love It: ✔️ Minutes to 25+ wineries & great restaurants ✔️ Easy drives to Sonoma, Calistoga, Healdsburg, Napa & the Coast ✔️ Great hiking in nearby parks ✔️ Birdwatching in the garden ✔️ Saltwater pool & bocce court ✔️ Stunning Mountain views ✔️ Private patio with gas grill & outdoor dining ✔️ Full kitchen, separate bedroom with ensuite bath

A wooden dock extends over the calm river, complemented by red Adirondack chairs and a matching umbrella. Lush greenery surrounds the area, providing a natural backdrop. The scene captures a peaceful riverside setting ideal for relaxation.

Cottage in Monte Rio

4.97 out of 5 average rating, 150 reviews

Sunny Riverfront Cottage

This lovely cottage is directly on the Russian River with gorgeous views. We've kept the original 1909 charm of the main living space while adding many new amenities. Your oasis awaits. BEFORE BOOKING: Be aware that the cozy second bedroom is not attached to the house, it is accessed through the main bedroom and a just few steps across the deck. You’ll enjoy the lovely bed, luxurious linens, fireplace and a great river view. See photos. NO PETS/SMOKING due to severe allergies. Thanks!

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, 218 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 favorite

The exterior of the private cottage is showcased with a modern design, featuring gray siding and large double doors that open to reveal the interior. Lush greenery is present around the entrance, complemented by potted plants. A wooden deck extends in front, enhancing outdoor access.

Cottage in Sonoma

4.99 out of 5 average rating, 262 reviews

Modern Farmhouse on Vineyard w Deck + Bocce Court

Escape to Sonoma in this bucolic slice of heaven with a Scandinavian-modern feel - just 9 minutes from Sonoma Square. Wake up to the sound of birds and enjoy your morning coffee outside, watching the sun come up over the rows of vines. Play a game of bocce in the 40' court or relax on the redwood deck overlooking neighboring vineyards, palms and ancient oaks by day; dine outdoors at night with a bottle of wine from one of the many world-class wineries within 10 minutes from the property.

Top guest favorite

An inviting outdoor space is surrounded by lush greenery and blooming lavender. Two wooden chairs are positioned to overlook sweeping views of the valley and vineyards below. A stone fire pit adds to the serene atmosphere of this natural setting.

Cottage in Penngrove

4.97 out of 5 average rating, 429 reviews

Sonoma Mountain Artist's Retreat

Enjoy the perched feeling of Sonoma Mountain's setting with sweeping views and nature. The slightly tamed wilderness with an olive orchard and gardens sets the tone as you chill on the redwood deck. This is a studio cottage with expansive views to the western valley and Marin. Mount Tam appears through the windows from your super comfy bed. This is a beautiful and unique space adjacent to a mellow artist's studio. NOTE: Well behaved and Pre-Approved dogs available for a nightly fee.

Top guest favorite

A spacious living area features a gray sofa adorned with plush pillows, complemented by a round accent chair. Natural light fills the room through large windows, highlighting a wooden coffee table with a decorative piece. Wooden beams create an inviting ambiance.

Cottage in Bodega Bay

4.99 out of 5 average rating, 941 reviews

Knix's Cabin at Salmon Creek

Our cabin has large picture windows providing views of Salmon Creek and the whitewater of the ocean. Our cabin is a cozy retreat for your getaway. Beachfront Access: A short and pleasant stroll from the cabin TOT tax ID is 1186N. Your stay supports the local community and complies with all regulations. Quiet Hours: 9:00pm to 7:00am Vacation Rental License No LIC25-0038 3075 Lucille Ave., Bodega Bay Property Owner: Lawler-Knickerbocker Certified Property Manager: Mary Lawler

A modern living area showcases a grey sofa adorned with plaid pillows. Above, three framed artworks feature intricate patterns against a navy blue wall. A wooden coffee table, centered with a vase of fresh flowers, completes the inviting space.

Cottage in Forestville

4.92 out of 5 average rating, 398 reviews

Nestled in Nature

A modern retreat in the Sonoma redwoods. The cottage is tucked away in the charming town of Forestville. Beneath the majestic redwoods, fir-covered hills, and the Russian river meandering toward Pacific shores. Forestville provides a wide variety of artisanal food, award winning restaurants and vineyards alike. An endless amount of outdoor activities from kayaking to hiking are nearly steps away.

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Popular amenities for Healdsburg cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a pool

Cottage in Sonoma

4.88 out of 5 average rating, 51 reviews

Luxury Sonoma Cottage: Sanctuary with Pool!

A private solar heated pool is surrounded by lush greenery and a stone patio. Several lounge chairs are positioned nearby for relaxation, with a shaded umbrella providing comfort. The pool's clear water reflects the blue sky, offering a serene atmosphere.

Cottage in Glen Ellen

4.97 out of 5 average rating, 62 reviews

Romantic Sonoma Creek Cottage With Pool & Spa

A solar-heated pool is set within a spacious patio of brick pavers. Two white lounge chairs sit beside the pool, accompanied by large umbrellas providing shade. Lush greenery and a wooden fence are visible in the background, enhancing the serene atmosphere.

Cottage in Sonoma

4.92 out of 5 average rating, 116 reviews

Farm Cottage With Private Pool

A row of colorful cottages is positioned along a wide, paved pathway. Each cottage features distinct hues and white trim, surrounded by lush greenery. The area appears well-maintained and inviting, with ample space between the units for privacy.

Cottage in Napa

Cozy cottage in Napa. Blue Note Jazz festival

A private hot tub is framed by brick and tile edging, with a smooth metal rail for easy access. Bubbles gently rise in the water, creating a relaxing atmosphere. Nearby, a larger swimming pool is visible, adding a sense of leisure to the space.

Cottage in Geyserville

4.41 out of 5 average rating, 260 reviews

The Cabernet Cabin

A spacious deck surrounds an unheated pool, featuring multiple lounge chairs and umbrellas. Scenic views of rolling hills and vineyards are visible in the background under a clear blue sky.

Cottage in Kenwood

4.83 out of 5 average rating, 6 reviews

Country 1BR Mountainview | Private Pool | Hot Tub

A clean and inviting pool area is showcased, featuring a recessed hot tub and a spacious swimming pool. In the background, a pergola provides shade over a seating area, with sunflowers and vineyard visible in the landscape.

Cottage in Sonoma

4.99 out of 5 average rating, 140 reviews

Idyllic Sonoma Vineyard Farmhouse With Pool

A spacious pool area features a shimmering blue pool surrounded by sun loungers and large umbrellas. Scenic views of rolling hills and vineyards are visible in the background, creating a serene atmosphere for relaxation.

Cottage in Kenwood

Vineyard-View 2BR Mountainview | Private Pool

Cottage rentals with a hot tub

A spacious outdoor deck is surrounded by towering redwoods, creating a serene setting. Comfortable seating arrangements include a sectional sofa with yellow cushions and a low coffee table. String lights illuminate the space, while potted plants add a touch of greenery.

Cottage in Guerneville

4.98 out of 5 average rating, 297 reviews

Hillside Retreat in the Redwoods w/ Hot Tub

Top guest favorite

A charming cottage features a well-maintained front yard adorned with lush greenery and colorful flowers. The inviting exterior showcases a mix of brick and stucco, with multiple arching doorways and windows, set against a tranquil evening sky.

Cottage in Junior College

4.99 out of 5 average rating, 106 reviews

Story-Book Cottage in the Heart of Wine Country

Top guest favorite

A quaint entrance is framed by a wooden overhang, featuring two yellow Adirondack chairs placed on a stone patio. Nearby, potted plants sit under a blooming tree, contributing to a serene outdoor setting.

Cottage in Santa Rosa

4.97 out of 5 average rating, 180 reviews

WiLD Vines Winery and Farm Cottage

A wooden deck extends over the calm water, connecting to a cottage with rustic shingle siding. Lush greenery frames the approach, and soft pastel colors in the sky suggest a tranquil sunset, enhancing the scenic atmosphere of the waterfront setting.

Cottage in Marshall

4.99 out of 5 average rating, 147 reviews

Tranquil waterfront cottage with private beach

Top guest favorite

A modern living space features large floor-to-ceiling sliding doors that open to a wrap-around deck. Skylights allow natural light to fill the room. Comfortable seating includes two patterned chairs and a leather chair, creating an inviting atmosphere for relaxation.

Cottage in Monte Rio

5 out of 5 average rating, 233 reviews

Riverfront Remodel | Hot Tub | Stunning Views

A two-story cottage is surrounded by lush greenery, featuring large windows that invite natural light. A wooden deck includes a picnic table and several seating chairs, positioned among ferns and flowering plants. A stone path leads to the garden area, enhancing the outdoor space.

Cottage in Monte Rio

4.96 out of 5 average rating, 110 reviews

garden in redwoods, hot tub, kayak, walk to river

Top guest favorite

The living room features a spacious sectional sofa paired with vibrant accent chairs, arranged around a natural fiber rug. A brick fireplace is the focal point, while large glass doors provide access to the outdoor area. Natural light floods the space through skylights and windows.

Cottage in Santa Rosa

4.97 out of 5 average rating, 228 reviews

Alpine Ranch Farmhouse ~ Wine Country

An open kitchen flows into a light-filled sitting area, where large windows offer views of the surrounding greenery. A wooden table is positioned near the window, and a bowl of fresh fruit sits on the kitchen island. Cozy seating with decorative pillows adds warmth to the space.

Cottage in Monte Rio

4.92 out of 5 average rating, 356 reviews

Riverside Retreat in Monte Rio

Pet-friendly cottage rentals

The entrance of the cottage is framed by a wooden gate leading to a gravel pathway. The facade showcases a cozy craftsman style with a gray exterior, white trim, and large windows. A welcoming wreath is placed on the front door, and the surrounding greenery adds to the charm.

Cottage in Santa Rosa

4.88 out of 5 average rating, 192 reviews

Cute Wine Country Cottage

A charming white house nestled among lush greenery, featuring a spacious deck and railing made of warm wood. Large windows invite natural light, and decorative wooden barrels add rustic charm to the outdoor area. The path is lined with pebbles, leading to the entrance.

Cottage in Forestville

4.96 out of 5 average rating, 105 reviews

Private Wine Country Bungalow! Sunny Treetop Views

A historic stone cottage is framed by lush greenery and well-maintained lawns. The front porch, supported by carved posts, provides a welcoming entrance. Surrounding palm trees add to the serene ambiance, enhancing the cottage’s character against a clear blue sky.

Cottage in Sonoma

4.88 out of 5 average rating, 138 reviews

Historic Cuneo Cottage Downtown Sonoma

A charming green cottage sits at the water's edge, featuring a vibrant red door. White Adirondack chairs are positioned on the deck, providing a serene view of Tomales Bay at sunset, with soft hues illuminating the sky and water.

Cottage in Marshall

4.89 out of 5 average rating, 304 reviews

Seaside Sanctuary • Perched Over the Bay • Dogs OK

The interior of the cottage features a spacious sleeping area with a king-sized bed, a soft sofa, and a leather love seat. A large window allows natural light, with curtains providing a touch of color. Nearby, a guitar and a small entertaining space can be seen.

Cottage in Middletown

4.98 out of 5 average rating, 128 reviews

Garden house with gas fireplace

The cottage is nestled among towering redwoods, featuring a large front porch and wooden steps leading to the entrance. A gravel path is surrounded by greenery, and a rustic outdoor area is visible on the side, enhancing the serene setting.

Cottage in Guerneville

4.86 out of 5 average rating, 111 reviews

Guerneville Cabin Among the Redwoods + Wineries

The exterior of Gravenstein Cottage features a welcoming porch with wooden steps leading up to a yellow framed entrance. Flourishing greenery surrounds the cottage, enhancing the natural ambiance of the serene woodland setting.

Cottage in Cazadero

4.9 out of 5 average rating, 349 reviews

Gravenstein Cottage

A cozy living area is filled with natural light, featuring a blue sectional sofa and a round coffee table topped with a neutral-colored book. Sheer curtains frame the window, and a plant adds a touch of greenery. A framed image is displayed on the wall.

Cottage in Glen Ellen

4.92 out of 5 average rating, 298 reviews

Cozy Creekside Retreat in Sonoma Wine Country

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