Once a sleepy hamlet of Sonoma County, Healdsburg is now acclaimed as a vibrant vacation haven where small-town charm is backdropped by beautiful landscapes of rolling hills and world-acclaimed wine-growing terroirs.
In Healdsburg, you can let your taste buds run wild with a varied array of organic eateries, artisan bakeries, and vintage wineries in a captivating town plaza.
Nestled among the Russian River, this beautiful historic town is graced by an eclectic range of hotels, which encompasses hip boutiques, California farmhouses, and restored Queen Anne homes. Here are the best cool and unusual hotels in Healdsburg, California (in no particular order)...
1. Harmon Guest House – a cool, trendy and Instagrammable hotel to stay in Healdsburg that provides free bikes to explore the area
A modern stitch in the fabric of Healdsburg’s history, Harmon Guest House harnesses a creative soul through a redwood-clad exterior and a sunny sculpture courtesy of NorCal artist Sabine Rickenwell.
Here, you will be greeted by a nature-inspired entrance, paying homage to Healdsburg’s innate landscape. The guestrooms are embellished with bold, contemporary local art, the check-in desk is formed from a giant fallen eucalyptus tree, and the main stairwell features an ascending flock of Blue Herons and golden floral, symbolizing the promise of new life, growth, and ascension.
At Harmon Guest House, you can gaze at breathtaking views of Fitch Mountain while sipping on a local glass of wine, or enjoy a bite around the firepit as the day descends into dusk.
- To book, check prices or availability for Harmon Guest House
2. H2hotel – an eco-friendly hotel that features a modern environment
Taking attention to detail to a whole new level, from bar to bathrooms, H2 Hotel is like a finely curated display of local artwork. The hotel has commissioned works that are rooted in Healdsburg’s beautiful culture while being conscious of the world at large.
An organic aesthetic is echoed in the 36 eco-chic rooms, which create a unique character through striped bamboo floors, funky Peace Industry rugs, topped with lush 100% Egyptian cottons.
This fresh and vibrant atmosphere is also expressed effortlessly through the hotel’s culinary offerings. From playful starters and handmade pastas to market-driven mains, the menu is as artful as the restaurant’s airy interior, and boasts a highly acclaimed cocktail programme.
- To book, check prices or availability for H2hotel
3. Montage Healdsburg – a polished and upscale hotel located on acres of vineyards and forest
The authentic charm and scenic beauty of Sonoma wine country is blended with a warm hospitality experience at this transformative hideaway, nestled among 258 acres of rolling vineyards and oak tree groves. Montage’s 130 bungalow-style guestrooms and suites boast an environmentally conscious design, with touches of contemporary influence and one-third of each space dedicated to outdoor living.
An exclusive spa treatment is on offer in the autumn months which features grape skins and seeds blended with the finest mineral salts and essential oils nurtured from the grounds of the resort.
Three signature dining options which include a seasonal poolside restaurant celebrate the bounty of the hotel’s lush environs.
- To book, check prices or availability for Montage Healdsburg
4. Hotel Trio Healdsburg – a stylish and pet-friendly hotel that is perfect for wine lovers
Blending intimacy with character, Hotel Trio has become a haven for tourists, wine excursionists, and those seeking a blissful Sonoma Country backdrop.
This gorgeous boutique adopts a pivotal point between familiar and surprising, and between splurge and smart, rooted in guiding guests to discover the best of the wine country while relaxing in a fresh, distinctive way.
Thoughtful amenities and a personalized service are designed to enhance the hospitality experience, while full kitchens offer a touch of convenience to the warm, over-sized accommodations. Grab & Go food options are readily available in the breakfast room, providing you with the fuel you need for a charming day out amid the graceful vineyards.
- To book, check prices or availability for Hotel Trio Healdsburg
5. Calderwood Inn – a quirky-chic B&B housed in a Victorian home style
An escape to a bygone era, this charming Queen Anne-style home was built in 1902 and is ran by a family of local winemakers. Set in English country gardens just minutes walk from the plaza and its surrounding boutiques, Calderwood Inn offers a cosy terrace and an inviting sitting room.
Enticing travellers from near and far to its seamless blend of romance and history, all of the rooms are exclusively designed with antique furnishings, while some of them feature skylights, ceiling murals, and stained-glass windows.
Plush beds and Italian linens add a touch of modern luxury. This grand hotel has also been recognized as one of the Green Leaders in the industry, reflecting Calderwood’s dedication to reducing its carbon footprint.
- To book, check prices or availability for Calderwood Inn
6. Rockhouse Suites – a modern oasis located in downtown Healdsburg
Surrounded by wine-tasting rooms and locally owned shops just steps from the Healdsburg Plaza, here we have a handful of newly renovated suites which boast opulent finishes and furnishings.
California King four-poster beds, beautiful fireplaces, and outside patios offer a touch of class to your deep dive into wine country. Double vanity bathrooms and marbled tiled showers complement the sleek and modern vibe in the suites, while some suites boast private courtyards to offer an open-air feel.
The Garden Suite boasts comfy outdoor furniture surrounded by roses and wisteria, greeting guests to a garden ambiance where families, friends, and couples can bask in the sun and soak up the charming natural surroundings.
- To book, check prices or availability for Rockhouse Suites
7. The Grape Leaf Inn – a cozy adult-only inn based in an English country-style gardens
Offering a luxury accommodation option to visitors of the Healdsburg area, the Great Leaf is another Queen Anne-style home and is blissfully situated in peaceful, English country-style gardens. Built in 1905, its 13 romantic rooms ooze a unique historic charm, with Italian linens embellishing the lavish king beds.
The ambiance of this award-winning property can be enjoyed alongside the owners’ portfolio of 9 artisan wineries, all within close proximity. A quirky, hidden speakeasy on-site serves the finest Californian wines and cheeses, and a sumptuous breakfast is served each morning.
Guests at the Grape Leaf Inn can enjoy an opulent open-air vibe from either the romantic terrace or the serene setting of the courtyard, backdropped by towering trees and an exclusive countryside ambiance.
- To book, check prices or availability for The Grape Leaf Inn
8. Hotel Les Mars – a historic French-style hotel close to major shops and restaurants
The surrounding grounds of Hotel Les Mars reflects the landscape of a historic French Maison, and brings the romance of European living to Northern California.
This stunning property is nestled amongst the hills of the Russian River Valley, close to Michelin Star dining and wine tasting spots, as well as a whole host of outdoor activities.
Dedicated to the tradition of old-world luxury, 17th and 18th -century antiques complement a unique Parisian-style charm, where meticulous attention to detail is etched into the hotel’s ethos.
A stunning limestone façade and wrought ironwork exterior greets guests to an exclusive experience, which is emanated inside through dramatic Flemish tapestry hangs and walnut panels.
- To book, check prices or availability for Hotel Les Mars
9. The River Belle Inn – a charming boutique inn that provides a beachfront view
You are invited to enjoy a special glass of red by the stunning Russian River, in this 1875 grand estate home. Located perfectly for a quaint stroll down to the plaza, or a charming bike ride through the vineyard, the unique history of the River Belle Inn allows you to kick back in style.
A refined hospitality experience awaits here, one that combines fresh cuisine amid one-of-a-kind surroundings with a graceful staff presence which prioritizes pin-point attention to detail.
Happy hours and made-to-order breakfasts can be enjoyed with the stunning backdrop of the river, and the inn’s charming common rooms offer a serene country setting to sit back and relax with friends and family.
- To book, check prices or availability for The River Belle Inn
10. Hotel Healdsburg – one of the most Instagrammable hotels in Healdsburg
Embracing the Sonoma Wine Country’s simplicity and charm, Hotel Healdsburg’s stunning location on the western edge of the historic town plaza puts you in close proximity to some of the world’s finest vineyards.
Talented Bay Area artists and designers have fabricated the hotel’s selection of artwork, ceramics, and furniture to enrich its connection to the surrounding beauty. Sky, cloud, and landscape paintings have been created to evoke an artisan atmosphere in the rooms, while the hand-thrown, organically glazed plates and cups have been custom-made to reflect a specific wine country terroir.
The renovated guestrooms echo the freshness and purity of Healdsburg through mute-coloured décor, and bedframes which evoke the rich, organic warmth of Northern California.
- To book, check prices or availability for Hotel Healdsburg
11. The Raford Inn – a stylish and laid-back B&B that has a very close connection to nature
This plantation-inspired Victorian Bed and Breakfast is gently perched on a south-facing slope above stunning Pinot Noir and Chardonnay vineyards, ringed by redwood forested mountains.
A welcoming beacon of hospitality, the grounds are graced with manicured gardens defined by soaring palms that are habitats to some of the region’s most exotic birds.
The property’s guestrooms are designed with ultimate comfort in mind, and are individually named after medicinal herbs and furnished with lavish, period antiques.
Some rooms boast fireplaces while others offer peaceful patios where you can sit and enjoy your morning coffee amid a divine ambiance. A short drive from the inn takes you to the natural wonders of the Sonoma Coast and the quaint fishing village of Bodega Bay.
- To book, check prices or availability for The Raford Inn
12. Duchamp Hotel – Downtown Healdsburg – easily one of the coolest hotels to stay in Healdsburg perfect for Millennials and Gen Zs
An urban oasis nestled in the very heart of Healdsburg’s downtown plaza, six exclusive, freestanding suites surround a lush outdoor pool and spa, and offer an indulgent experience of unmatched privacy and convenience.
Each suite boasts contemporary lines and plush bedding and is adorned with bespoke touches which reflect a chic, European design.
A private, enclosed patio provides the intimacy and ambiance of a quaint boutique hotel, where you can enjoy a glass of the Duchamp’s exclusive collection of fine wines. Alternatively, you can lounge by the pool and enjoy the harmonic cacophony of birds singing in the olive trees, before heading out to enjoy the treasures of the Wine Country on your doorstep.
- To book, check prices or availability for Duchamp Hotel – Downtown Healdsburg
13. Healdsburg Inn on the Plaza, A Four Sisters Inn – a contemporary bed and breakfast that offers a homely vibe
Boasting the optimum location in the historic Healdsburg Plaza, this classic California inn, built in 1901, blends a sophisticated and intimate setting with signature amenities and a top rate service.
The architectural details in the 12 guestrooms include high ceilings and original mouldings, which beautifully complement the bay windows and the state-of-the-art amenities on offer.
The well-appointed bathrooms contain either jetted spa tubs or antique claw foot tubs, and guests can enjoy bespoke wine & cheese tasting sessions as a gesture of good will from the staff who embody a spirit of five-star hospitality. A complimentary concierge service is also on hand to help you get the most out of your Healdsburg getaway.
- To book, check prices or availability for Healdsburg Inn on the Plaza, A Four Sisters Inn
14. The Madrona – an elegant and sophisticated hotel that offers stunning views of California’s Wine Country
Toeing the line between elegance and extravagance in surprisingly harmonious ways, The Madrona has taken the building’s Victorian bones and transformed it into a haven of lush relaxation.
Whether you’re admiring the refined interior or the neighbouring forest, gracious views fill every visual frame in the property. From the whimsical light fixtures to the inspired upholstery fabrics, each room is unique, sharing nods to both past and present.
The Madrona invites you to wake up to misty mornings, before peacefully meandering the leafy pathways and storied hallways and getting lost in the magic of the surroundings. To end the day, you can revel in a convivial feast with kindred spirits, backdropped by tangerine-hued sunsets over the emerald gardens.
- To book, check prices or availability for The Madrona
15. Wildhaven Sonoma Glamping – an unassuming resort where guests can explore a glamping experience, ideal for a romantic stay
Seamlessly combining nature and comfort to help you recharge mind, body, and soul, Wildhaven Glamping invites you to reconnect with loved ones and rediscover your love for mother nature.
Creating an elevated outdoor lodging experience in the heart of Sonoma Wine Country, the safari-style canvas tent cabins boast the furnishings and plushness of a boutique hotel, with the rustic atmosphere of an outdoor retreat.
The 10-acre property features its very own river access point, as well as a store with local treats, and activities such as yoga, wine tasting, and live music. A visit to this upscale yet affordable site puts you within arm’s reach of hiking trails, among other memorable outdoor excursions.
- To book, check prices or availability for Wildhaven Sonoma Glamping
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My first true adventure began as a six month voyage around South East Asia as a fresh faced backpacker and ever since I’ve lived a semi nomadic existence, clocking up visits to over 40 countries. I’m a lover of US Road Trips, deserted beaches bathed in warm glow of a sunset, Cuban mojitos, travel destinations far away from the tourist crowds and all things Scandinavian – from cloudberry liquors to Nordic noirs. When not wandering the world and running Global Grasshopper, you’ll find me walking my rescued Greek street dog in leafy South West London, strolling around the Brighton Lanes on random day trips, hunting for photogenic landscapes or daydreaming about my favourite places; Havana, Copenhagen, Italy, Laos, California and the surreally beautiful landscapes of a wintry Iceland.