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157 Lodgings in Healdsburg, CA
9.8 133 reviews
Healdsburg, CA
07/10 – 07/13
$1418/nighttotal: $4254 (3 )
Haven With Pool, Hot Tub And Tastings Included
2 2
house , Healdsburg
Private Vineyard Haven is located in Healdsburg, California, just a short drive from the Charles M. Schulz Sonoma County Airport and the Luther Burbank Center for the Arts. The property has earned excellent ratings for its location, cleanliness, and overall user experience. This 2-bedroom house features a fully equipped kitchen, air conditioning, and a private patio and balcony with mountain views. Guests can enjoy amenities like a swimming pool, Jacuzzi, tennis court, and a spa, as well as nearby cycling trails and easy access to local attractions.
10 52 reviews
Healdsburg, CA
07/10 – 07/13
$687/nighttotal: $2061 (3 )
Downtown Healdsburg Perch
1 2
apartment , Healdsburg
This Healdsburg apartment boasts a unique location atop a Quonset Hut building overlooking Healdsburg Plaza, placing you steps from rooftop bars, restaurants, tasting rooms, and shops. The one-bedroom, one-bathroom unit offers a luxurious, spacious design with a spa-like bathroom, cozy living room, quiet bedroom, and convenient kitchenette; it comfortably accommodates two guests and features stunning views from its top-floor position.
10 10 reviews
Healdsburg, CA
06/20 – 06/27
$2387/nighttotal: $16709 (7 )
Wine Country Estate
1 2
house , Healdsburg
This 5-bedroom, 6-bathroom estate offers unparalleled privacy in the rolling hills surrounding Healdsburg, providing a secluded yet accessible wine-tourism experience ideal for large groups. This luxurious rental boasts a private tennis court and swimming pool, with expansive interior rooms perfect for entertaining, and is situated a short drive from Healdsburg's renowned wineries and vineyards.
Healdsburg, CA
07/10 – 07/13
$528/nighttotal: $1584 (3 )
Private Acre With Bbq Patio 5min To Healdsburg Plaza
1 2
house , Healdsburg
This Healdsburg rental house is located on a private acre, offering seclusion and is situated 5 minutes from the Healdsburg Plaza. This 960 sq ft house accommodates up to 7 guests and includes a fully equipped kitchen, 2 bathrooms, air conditioning, and on-site casino and proximity to cycling routes.
9.7 156 reviews
Healdsburg, CA
07/10 – 07/13
$818/nighttotal: $2454 (3 )
Modern Home In Hburg Wine Country
1 2
apartment , Healdsburg
This 3-bedroom, 4-bathroom apartment is only a few miles from Healdsburg's town square, giving easy access to the city's attractions. With excellent user, location, and cleanliness ratings, this modern open design apartment offers abundant natural light and a fully equipped kitchen. Accommodating up to 6 guests, the apartment features expansive decks and open spaces for indoor-outdoor living. Guests can enjoy access to outdoor activities such as boating, fishing, hiking, and kayaking, as well as amenities like air conditioning, a garden, parking, and exterior security cameras for added peace of mind.
9.3 1705 reviews
Healdsburg, CA
08/13 – 08/16
$694/nighttotal: $2082 (3 )
Worldmark Windsor
3 10
resort , Windsor
Worldmark Windsor is located in the Russian River Valley, adjacent to the Windsor Golf Club and just 1.5 miles from the Santa Rosa Airport. The resort has received excellent ratings for location, cleanliness, and overall user experience. The resort offers spacious apartments with full kitchens, separate living areas, and in-unit laundry facilities. Guests can enjoy a variety of amenities, including outdoor pools, hot tubs, a fitness center, a spa, tennis courts, and a children's play area.
9.4 76 reviews
Healdsburg, CA
07/10 – 07/13
$953/nighttotal: $2859 (3 )
Cottages At Little Saint
1 2
resort , Healdsburg
Cottages At Healdsburg is located in Healdsburg, a short walk from the Raven Performing Arts Theater and Russian River, and within a five-minute drive of the Healdsburg Center for the Arts and Healdsburg Plaza. The cottages have received excellent user ratings, with very good scores for location and cleanliness. Each cottage can accommodate two guests and features a private pool, fireplace, and furnished balcony or patio. Guests can also enjoy the seasonal outdoor pool, concierge services, free WiFi, and pillowtop beds.
10 7 reviews
Healdsburg, CA
06/20 – 06/27
$925/nighttotal: $6475 (7 )
Right In The Heart Of Healdsburg Lies This Charming Two-bedroom House
2 2
apartment , Healdsburg
This cozy Healdsburg house offers a central location, providing easy access to nearby wineries like Pezzi King and Seghesio Family Vineyards, as well as outdoor spaces such as Safari West and Healdsburg Ridge Open Space Preserve. The two-bedroom, one-bathroom home comfortably sleeps four guests and includes amenities such as Wi-Fi, air conditioning, a fridge, and a microwave; nearby culinary destinations include SingleThread Farm at Dry Creek and Dom Whitney Tasting Lounge.
9.8 11 reviews
Healdsburg, CA
08/13 – 08/16
$2073/nighttotal: $6219 (3 )
Modern Retreat - Spectacular View Above Dry Creek
1 10
apartment , Healdsburg
This apartment is located in the heart of Healdsburg, within walking distance of the town square and numerous wineries. It has excellent user, location, and cleanliness ratings. The apartment is spacious and comfortable, with 5 bedrooms, 3 bathrooms, and a guest capacity of 10. It has a fully equipped kitchen, comfortable furnishings, free Wi-Fi, a private patio, and on-site parking. It also allows well-behaved pets for an additional fee.
10 129 reviews
Healdsburg, CA
07/10 – 07/13
$510/nighttotal: $1530 (3 )
2 Bedroom Flat In Downtown Healdsburg
1 2
apartment , Healdsburg
This centrally-located apartment is tucked away in a building surrounded by restaurants, bars, and tasting rooms just a few blocks from the historic downtown plaza of Healdsburg. With excellent user, location, and cleanliness ratings, this apartment offers a comfortable stay for up to 4 guests with 2 bedrooms and 1 bathroom. The apartment features a modern and artistic interior design, with paintings, sculptures, and artistic touches around every corner. It has a fully functioning kitchen with brand new state-of-the-art appliances and cookware, a dedicated workspace, and a large living space with a leather sectional sofa and coffee table. Guests also have access to wine tasting and an organic grocery store just steps from the front door.
10 109 reviews
Healdsburg, CA
07/10 – 07/13
$833/nighttotal: $2499 (3 )
Modern, Secluded Retreat - Walk To The Plaza!
1 2
apartment , Healdsburg
This modern cottage is located in Healdsburg, just a 15-minute walk from the Healdsburg Plaza, offering easy access to shops, restaurants, and attractions. It's also situated on Dry Creek, providing a peaceful retreat from the bustling town. This cottage has received excellent ratings for its location, cleanliness, and overall user experience. This 1,150 square foot cottage comfortably sleeps six guests in its two bedrooms and three bathrooms. Guests can enjoy a fully equipped kitchen, a private jacuzzi, a spacious deck, and access to the river for relaxing and enjoying the beautiful California weather.
10 1 review
Healdsburg, CA
07/10 – 07/13
$615/nighttotal: $1845 (3 )
Private Acre+bbq Patio | 5min To Healdsburg Plaza
2 2
apartment , Healdsburg
This 2-bedroom, 2-bathroom cottage is situated on a one-acre property just outside Healdsburg, offering a private retreat 5 minutes from Downtown Healdsburg Plaza and a 7-minute drive to Memorial Beach on the Russian River. This newly remodeled 960-square-foot rental accommodates up to 4 guests with a fully equipped kitchen, air conditioning, private patio with BBQ, and parking for three vehicles, providing an ideal base for exploring nearby Dry Creek Valley wineries.
Traveler-Approved Family-Friendly Accommodations in Healdsburg, CA
Getting the lodging right makes all the difference for a family trip to Healdsburg, CA, with city attractions within easy reach at every selected option.
9.4 3 reviews
Healdsburg, CA
08/13 – 08/16
$1737/nighttotal: $5211 (3 )
Exceptional Estate Vineyards In Healdsburg Sonoma County
5 10
house , Windsor
This Windsor villa, near Chalk Hill Estate Vineyard (1.5 km) and the Russian River (4.9 mi), offers easy access to wine tasting and scenic beauty, with additional attractions like Powell's Sweet Shoppe and Dom Whitney Tasting Lounge within 6 miles. This 6,000-square-foot, five-bedroom, four-bathroom home accommodates up to 10 guests and features a fully equipped kitchen, private patio, garden, and parking; housekeeping is available upon request.
9.6 21 reviews
Healdsburg, CA
07/10 – 07/13
$515/nighttotal: $1545 (3 )
River Retreat - Hot Tub And Tastings Included
2 2
apartment , Healdsburg
This Healdsburg bungalow, situated in a peaceful neighborhood just five minutes from downtown Healdsburg and directly across from the Russian River, offers easy access to kayaking, swimming, and local restaurants. This two-bedroom, one-bathroom rental sleeps six guests comfortably, boasting a fully equipped kitchen, private hot tub, outdoor decks with a gas BBQ and ping pong table, and proximity to Healdsburg's tasting rooms and shops.
Healdsburg, CA
08/13 – 08/16
$2653/nighttotal: $7959 (3 )
Modern Wine Country Home On 10 Acres With Vineyard
6 10
house , Healdsburg
This 3-bedroom Healdsburg villa is located 5 miles from Healdsburg Plaza and 12 miles from Charles M. Schulz–Sonoma County Airport, offering easy access to attractions like Safari West and Petrified Forest within a 25-mile radius. The 10-acre property features a vineyard with stunning views, a fully equipped kitchen, a private balcony, free Wi-Fi, parking, and accommodates up to 11 guests.
9.2 64 reviews
Healdsburg, CA
07/10 – 07/13
$559/nighttotal: $1677 (3 )
Mountain Cottage Near Russian River, Hiking & Downtown, Family And Pet Friendly
3 2
cottage , Healdsburg
This charming cottage is located just a short walk from the Russian River and a 10-minute drive from downtown Healdsburg, offering a peaceful retreat surrounded by redwood trees and mountain views. Reviewers consistently rate this rental "excellent" for its comfortable accommodations and convenient location. This 3-bedroom, 2-bathroom home comfortably sleeps 6 guests and offers 1100 square feet of living space. Enjoy modern amenities like a fully equipped kitchen, a relaxing spa, a private garden, and a spacious deck with a BBQ grill, perfect for enjoying meals and relaxing in the fresh air.
Best Healdsburg, CA lodging with a pool
Among the 157 accommodations in Healdsburg, CA, here are the 4 best ones with a pool
This Healdsburg estate home is located just north of the town of Healdsburg, in Sonoma County's Wine Country, on a private 1.65-acre property, a short drive to both the Russian River and the Pacific Ocean. It has excellent ratings for user experience, location, and cleanliness. This luxurious rental offers four bedrooms, three bathrooms, and can accommodate up to ten guests. It features a private oasis with a large pool, a spa, a bocce ball court, an expansive outdoor kitchen, a game room with a ping pong table, a pool table, and a vintage Pac-Man table, as well as a gourmet kitchen with a chef-friendly layout.
Healdsburg, CA
08/13 – 08/16
$4948/nighttotal: $14844 (3 )
Luxury Healdsburg Estate & Vines
5 10
apartment , Healdsburg
This resort-style estate, recently rebuilt after the 2019 Kincade Fire, is located in Healdsburg within the Alexander Valley vineyards, offering proximity to the Russian River and Safari West, with Calistoga Hot Springs a short drive away. This 5-bedroom, 5-bathroom villa accommodates up to 12 guests and features a pool, hot tub, chef's kitchen, and a dedicated 'Barn' area with an arcade, bocce court, and BBQ, all providing jaw-dropping vineyard and wine country views.
10 24 reviews
Healdsburg, CA
08/13 – 08/16
$4936/nighttotal: $14808 (3 )
Spectacular View Estate 5min Away
4 10
apartment , Healdsburg
This luxurious 12-acre estate is located in the Dry Creek/Lytton Springs wine country, just a 5-minute drive from the heart of Healdsburg. This property has received excellent reviews for its amenities and service. The home features a spacious 4,000 square-foot layout with 5 bedrooms and 5 bathrooms, comfortably accommodating up to 12 guests. Guests can enjoy a private pool and hot tub, a full-size bocce court, an outdoor fire pit, a gourmet kitchen, and a private in-law unit.
10 5 reviews
Healdsburg, CA
06/20 – 06/27
$1517/nighttotal: $10619 (7 )
Escape To Dry Creek Valley In Healdsburg In A Beautifully Renovated Farm House
4 2
apartment , Healdsburg
This Dry Creek Valley farmhouse rental is minutes from Healdsburg's downtown restaurants and galleries, and a short walk from the Dry Creek General Store. The 4-bedroom, 4-bathroom property sleeps 8 guests and includes a pool, hot tub, party barn with a queen sofa bed, fully equipped kitchen, and a Sonos sound system.
Frequently Asked Questions about accommodations in Healdsburg, CA
What are the must-see sites in or near Healdsburg, CA?
Healdsburg is known for its beautiful scenery and wineries. You should definitely check out the Healdsburg Plaza, a charming square with shops and restaurants. For a scenic drive, take Highway 128 to the Russian River. You can also visit the historic town of Cloverdale, about 20 miles north of Healdsburg.
What are the best accommodations in Healdsburg, CA?
The closest airport to Healdsburg is Charles M. Schulz–Sonoma County Airport (STS), about 30 miles away. You can also drive from San Francisco, which is about an hour and a half away, or from Sacramento, which is about two hours away.
What are the best accommodations with a pool in Healdsburg, CA?
What outdoor activities can visitors enjoy in and around Healdsburg, CA?
Healdsburg is surrounded by beautiful natural areas, perfect for hiking and biking. You can explore the Healdsburg Ridge Trail, which offers stunning views of the valley, or visit the Armstrong Redwoods State Natural Reserve, where you can walk among towering redwood trees. For a more relaxing experience, you can go kayaking or canoeing on the Russian River.
What are the best accommodations with a jacuzzi in Healdsburg, CA?
When is the ideal time to plan a trip to Healdsburg, CA?
Healdsburg is beautiful year-round, but the best time to visit is during the spring and fall. The weather is mild and the crowds are smaller. If you are interested in wine tasting, the harvest season in the fall is a great time to visit.
What are the best accommodations for families and kids in Healdsburg, CA?
What are the best walking or cycling routes in Healdsburg, CA?
The Healdsburg Plaza is a great place to start a walk or bike ride. You can explore the downtown area, which is full of charming shops and restaurants. For a longer ride, try the Healdsburg to Windsor Trail, which follows the Russian River for 12 miles. You can also bike to the nearby town of Sebastopol.
What are the best pet friendly accommodations in Healdsburg, CA?
What nearby towns or cities can be explored from Healdsburg, CA?
Healdsburg is a great base for exploring the Sonoma County region. You can easily visit the charming towns of Santa Rosa, Sebastopol, and Guerneville. For a day trip, you can drive to the coast and visit the town of Bodega Bay, known for its beautiful beaches and seafood.
What are the best accommodations with parking in Healdsburg, CA?
What amenities can travelers expect from accommodations in Healdsburg, CA?
Healdsburg offers a wide range of accommodations, from cozy bed and breakfasts to luxurious hotels. Many hotels offer amenities like pools, spas, and restaurants. You can also find vacation rentals, which are a great option for families or groups.
Destinations nearby
Best Healdsburg, CA accommodation with a garden
9.9 97 reviews
Healdsburg, CA
07/10 – 07/13
$1370/nighttotal: $4110 (3 )
Homestead With Pool And Hot Tub - Wine Tastings Included
3 2
house , Healdsburg
This Healdsburg vacation home offers a peaceful retreat in the heart of Sonoma County wine country, just minutes from the renowned Luther Burbank Center for the Arts. The house has received excellent ratings for its location, cleanliness, and user experience. The house has three air-conditioned bedrooms and two bathrooms, and can accommodate up to seven guests. The 1,700-square-foot house has a fully equipped kitchen, a private pool, a Jacuzzi, a garden, a tennis court, and parking. Children will enjoy the on-site playground, while adults can explore the scenic Healdsburg countryside on the nearby cycling trails.
9.8 169 reviews
Healdsburg, CA
08/13 – 08/16
$2031/nighttotal: $6093 (3 )
Trinite Estate
1 10
house , Windsor
This exceptional vineyard estate is located in the Chalk Hill district of the Russian River Valley appellation, just a short drive from the charming town of Windsor. The property has excellent user, location, and cleanliness ratings. The villa offers four private bedrooms and a detached guest suite, accommodating up to 10 guests. Amenities include a private wine tasting, a tour of the estate's vineyard and winery, outdoor living spaces, and private chef services.
10 196 reviews
Healdsburg, CA
07/10 – 07/13
$2617/nighttotal: $7851 (3 )
5 Bedroom, 6.5 Bath Luxury Home On 3+ Acres, 5 Min To Square
5 2
apartment , Healdsburg
This family-friendly vacation home is located in a peaceful rural setting just outside of Healdsburg, within a 3km radius of the Healdsburg Plaza, Museum, and Raven Performing Arts Theater. This property has received excellent user ratings and is perfect for families or groups of friends. The home features 5 bedrooms and 7 bathrooms, spanning 4,600 square feet, and comfortably accommodates up to 12 guests. Enjoy a private pool, fenced yard, sauna, spa tub, fully equipped kitchen, fireplace, and other modern amenities for a relaxing and enjoyable stay.
10 218 reviews
Healdsburg, CA
07/10 – 07/13
$380/nighttotal: $1140 (3 )
Bee Haven Cottage
1 2
apartment , Healdsburg
This cottage is located in Healdsburg and has received excellent user, location, and cleanliness ratings. It is ideal for a couple, featuring one bedroom and one bathroom. The cottage comes with a kitchen equipped with a fridge and microwave, air conditioning, a jacuzzi, a garden, and parking. Guests can enjoy the peace and quiet of the garden or take advantage of the nearby attractions.
Best Healdsburg, CA accommodation with a kitchen
10 2 reviews
Healdsburg, CA
08/13 – 08/16
$1527/nighttotal: $4581 (3 )
Healdsburg Gorgeous Farmhouse For 10, Pool,spa,bbq
4 10
apartment , Windsor
This Healdsburg vacation home, near Porter Creek Vineyards (2.4 miles) and the Russian River (3.1 miles), offers easy access to renowned wineries like Russian River Vineyard and Hartford Family Winery within a 6-mile radius. This 2,500-square-foot house boasts four bedrooms, three bathrooms, and accommodates up to 12 guests, featuring a private pool, hot tub, outdoor barbecue grills, and in-house laundry facilities.
Healdsburg, CA
06/20 – 06/27
$2406/nighttotal: $16842 (7 )
Five-star Resort-like Property
1 2
apartment , Healdsburg
This Healdsburg apartment is tucked away in a peaceful and secure neighborhood, just a short drive from the town's charming downtown with its award-winning wineries, restaurants, and shops. The apartment is located on a two-acre property and includes a kitchen garden, offering plenty of space for relaxation and exploration. This two-bedroom, two-bathroom rental comfortably accommodates four guests. The apartment has a spacious layout and features a swimming pool, jacuzzi, fitness center, and parking.
10 2 reviews
Healdsburg, CA
06/20 – 06/27
$2810/nighttotal: $19670 (7 )
Luxurious Enchanting Healdsburg Estate Style Retreat, Sleeps 12, Pool, Firepit
6 2
apartment , Healdsburg
This Healdsburg estate rental, near the Russian River and a 5-minute drive (1.83 miles) from Healdsburg Plaza, offers unparalleled privacy on a gated property with river views. The 5300+ square-foot family compound features six bedrooms, seven bathrooms, and accommodates up to twelve guests, boasting a solar-heated pool (seasonal), hot tub, and various recreational amenities including a bocce ball court, horseshoe pit, and basketball hoop.
9.8 15 reviews
Healdsburg, CA
08/13 – 08/16
$1096/nighttotal: $3288 (3 )
Petunia's Place: Landmark 1857 Farmhouse With Hot Tub, Across From Sunset Beach
5 10
farm , Forestville
Petunia's Place is a charming farmhouse located in Forestville, just across the highway from Sunset Beach and a short drive from the Russian River and Armstrong Redwoods State Park. The area offers a peaceful escape with easy access to the natural beauty of the Sonoma Coast. This 1470 square foot farmhouse comfortably accommodates up to 10 guests in its 5 bedrooms and 3 bathrooms. Enjoy unique features like a Foosball Funroom bedroom, a private backyard with a wooden deck and gas BBQ, and a blend of vintage charm and modern amenities.