Title: Book the Best Healdsburg LUXURY Hotels - Upscale Hotels in Healdsburg, CA | Expedia.ca [Hotels in Healdsburg](https://expedia.ca/Healdsburg-Hotels.d8322.Travel-Guide-Hotels)[Vacation Rentals in Healdsburg](https://expedia.ca/Healdsburg-Vacation-Rentals.d8322.Travel-Guide-VacationRentals)[Flights to Healdsburg](https://expedia.ca/Cheap-Flights-To-Healdsburg.d8322.Travel-Guide-Flights)[Healdsburg Car Rentals](https://expedia.ca/Car-Rentals-In-Healdsburg.d8322.Car-Rental-Guide)[Healdsburg Vacation Packages](https://expedia.ca/Healdsburg.d8322.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/215000/215993-Healdsburg-Sc.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find luxury hotels in Healdsburg, CA ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Healdsburg Luxury Hotels Tonight [Sep 27 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2025-09-27&endDate=2025-09-28&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 28 - Sep 29](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2025-09-28&endDate=2025-09-29&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2025-10-03&endDate=2025-10-05&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2025-10-10&endDate=2025-10-12&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Healdsburg Luxury Hotels ![Gazebo](https://images.trvl-media.com/lodging/1000000/130000/126600/126590/b9d4555c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/130000/126600/126590/01dd0506.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/126600/126590/b53a16af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/130000/126600/126590/a13c1a8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Vinea, a Travelodge by Wyndham Healdsburg 7.4/10 Good (686) "Room was clean and spacious, nice and friendly staff." CA $149 CA $173 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Healdsburg-Hotels-Hotel-Vinea.h126590.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/3000000/2940000/2937700/2937684/aab76a75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Carriage House](https://images.trvl-media.com/lodging/3000000/2940000/2937700/2937684/2f737a58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/3000000/2940000/2937700/2937684/f54c10e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Carriage House | Living area](https://images.trvl-media.com/lodging/3000000/2940000/2937700/2937684/52bc5b16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Healdsburg Inn on the Plaza, A Four Sisters Inn Healdsburg 8.6/10 Excellent (561) "Very nice breakfast and great location. " CA $349 CA $406 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Healdsburg-Hotels-Healdsburg-Inn-On-The-Plaza.h2937684.Hotel-Information) ![Outdoor pool, open 9:00 AM to 9 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1120000/1111500/1111427/55aee5ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1120000/1111500/1111427/fa1e8da8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1120000/1111500/1111427/672f109d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Jetted Tub](https://images.trvl-media.com/lodging/2000000/1120000/1111500/1111427/d3e1f564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairview Inn and Suites Healdsburg 7.8/10 Good (1001) "Very Clean and Modern. Would definitely stay again." CA $153 CA $178 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Healdsburg-Hotels-Fairview-Inn-And-Suites.h1111427.Hotel-Information) ![Suite, 1 King Bed, Non Smoking, Fireplace (with Sofabed) | Living area](https://images.trvl-media.com/lodging/1000000/20000/19400/19399/f85bb490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/19400/19399/98fa2a2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/19400/19399/992810dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/19400/19399/2ee3c403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Dry Creek Inn Healdsburg 8.0/10 Very good (1012) "Very welcoming good location." CA $194 CA $226 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Healdsburg-Hotels-Best-Western-Dry-Creek-Inn.h19399.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/4000000/3620000/3618400/3618334/92a67a3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, Multiple Beds, City View (Eco Suite) | View from room](https://images.trvl-media.com/lodging/4000000/3620000/3618400/3618334/3547a324.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/4000000/3620000/3618400/3618334/d73147d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/4000000/3620000/3618400/3618334/3c890403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### H2Hotel Healdsburg 9.4/10 Exceptional (690) "Perfect location if you are trying to get away for the weekend and doing some wine tasting dining a little bit of shopping. Everything is walking distance from this location and hotel itself is really nice. " CA $390 CA $509 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Healdsburg-Hotels-H2hotel.h3618334.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1640000/1639800/1639752/808f26c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds (Mansion)](https://images.trvl-media.com/lodging/2000000/1640000/1639800/1639752/d3e96341.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/2000000/1640000/1639800/1639752/75cedea1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1640000/1639800/1639752/9e796a87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 27 North Healdsburg 9.6/10 Exceptional (297) "Great hotel in Healdsburg. " CA $704 CA $874 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Healdsburg-Hotels-Hotel-Les-Mars.h1639752.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/460000/451700/451693/ac03bc94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; alfresco dining](https://images.trvl-media.com/lodging/1000000/460000/451700/451693/22bb25b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/460000/451700/451693/80a9d8d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/460000/451700/451693/w1497h2000x3y0-290c2ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Madrona Healdsburg 9.6/10 Exceptional (36) "Wonderful stay at this beautiful old Manor House beautifully appointed with antique furniture. Our second time there and would definitely return." CA $490 CA $618 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Healdsburg-Hotels-The-Madrona.h451693.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/790000/786900/786805/9d93bedd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/790000/786900/786805/d4bf0fc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/1000000/790000/786900/786805/f34d8bbb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/790000/786900/786805/38211be6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Healdsburg Healdsburg 9.2/10 Wonderful (420) "Beautiful hotel in a prime location adjacent to the square in downtown Healdsburg. Every member of the hotel staff from the front desk to the bartender and wait staff we’re all so friendly and helpful. The pool area was beautiful and also had friendly and attentive waitstaff. Definitely recommend this hotel. " CA $626 CA $800 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Healdsburg-Hotels-Hotel-Healdsburg.h786805.Hotel-Information) ![Executive Room, 1 King Bed | Terrace/patio](https://images.trvl-media.com/lodging/7000000/6950000/6948800/6948795/a77aa9d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Room, 1 King Bed | Terrace/patio](https://images.trvl-media.com/lodging/7000000/6950000/6948800/6948795/96f03827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/7000000/6950000/6948800/6948795/33fed1e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Room, 1 King Bed](https://images.trvl-media.com/lodging/7000000/6950000/6948800/6948795/f7fd01b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Calderwood Inn Healdsburg 9.2/10 Wonderful (241) "Lovely historic house, conveniently located close to the square. The staff was very helpful and the breakfast was delicious." CA $384 CA $445 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Healdsburg-Hotels-Calderwood-Inn.h6948795.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-11&endDate=2025-10-12®ionId=8322&adults=2&star=50&sort=RECOMMENDED&openPlayBack=true) ## Find out more about Healdsburg ### Healdsburgand its attractions for luxury travelers Healdsburg, California, is a delightful haven for luxury travellers seeking both relaxation and adventure. Begin your journey at the iconic \*\*Healdsburg Plaza\*\*, where boutique shops and gourmet restaurants await, perfect for indulging in artisanal delicacies and local wines. Just a short stroll away, the \*\*Healdsburg Museum and Historical Society\*\* offers a glimpse into the town's rich heritage, providing a cultural backdrop to your stay. For wine enthusiasts, a visit to the \*\*Jordan Vineyard & Winery\*\* is a must; their elegant tastings paired with stunning views of the vineyards create an unforgettable experience. Outdoor lovers can explore the \*\*Russian River\*\*, where kayaking or a leisurely float offers both adventure and tranquility amidst beautiful natural scenery. If you're looking to unwind, the \*\*Fairmont Sonoma Mission Inn & Spa\*\* nearby offers luxurious spa treatments that will leave you feeling rejuvenated. Staying in the heart of Healdsburg allows you to easily navigate these experiences, with several upscale hotels like \*\*Hotel Healdsburg\*\* providing exceptional service, exquisite dining, and beautifully designed rooms that reflect the charm of Wine Country. Here, every detail is considered, making your stay not just comfortable, but truly memorable. ### Find the best luxury hotels and resorts in Healdsburg Healdsburg is a stunning destination known for its picturesque vineyards and upscale offerings. For those seeking a luxurious stay, here are some top hotel recommendations that promise a lavish experience. [27 North](https://www.expedia.ca/Healdsburg-Hotels-Hotel-Les-Mars.h1639752.Hotel-Information) - **Why it's great for a luxury retreat:** 27 North epitomises luxury with a remarkable review rating of 9.6, making it a top choice for discerning travellers. This boutique hotel features premium bedding, designer toiletries, and elegant bathrobes, ensuring guests experience the utmost comfort. With a dedicated concierge service, guests can enjoy tailored recommendations and reservations during their stay. - **Other amenities:** Guests can indulge in a stocked minibar with complimentary items and daily housekeeping services. The hotel also offers access to local wineries and nearby golf courses, perfect for those wanting to explore Healdsburg's scenic beauty. With its inviting fireplace and child-friendly window design, this hotel provides a luxurious yet homely atmosphere. - **Nearby attractions:** Healdsburg Plaza - 0.3 km, Healdsburg Center for the Arts - 0.3 km, Healdsburg Museum - 0.6 km [H2Hotel](https://www.expedia.ca/Healdsburg-Hotels-H2hotel.h3618334.Hotel-Information) - **Why it's great for a luxury retreat:** H2Hotel stands out as an ideal choice for luxury travelers, an impressive guest review rating of 9.4. This contemporary hotel offers an array of upscale amenities, including exquisite bathrobes and designer toiletries, ensuring a pampered stay. Guests can indulge in the serene spa facilities or relax by the outdoor pool, all while enjoying spectacular mountain views from their suites. - **Other amenities:** In addition to luxury comforts, H2Hotel features a fully equipped fitness centre and an onsite winery for tastings, enhancing the wine country experience. Travelers can also take advantage of complimentary breakfast, valet parking, and daily housekeeping. With treatment rooms for various spa treatments, yoga classes, and relaxing sun loungers by the pool, guests will find everything they need for a rejuvenating retreat. - **Nearby attractions:** Healdsburg Plaza - 0.2 km, Healdsburg Center for the Arts - 0.4 km, Healdsburg Museum - 0.4 km [Hotel Healdsburg](https://www.expedia.ca/Healdsburg-Hotels-Hotel-Healdsburg.h786805.Hotel-Information) - **Why it's great for a luxury retreat:** Hotel Healdsburg is a premier luxury destination, garnering a stellar review rating of 9.2. This boutique hotel features upscale amenities such as Frette Italian sheets, bathrobes, and a deep soaking bathtub for a truly indulgent experience. With its exquisite couples dining options and concierge services, guests can revel in a sophisticated and personalised stay. - **Other amenities:** Beyond its luxurious offerings, Hotel Healdsburg boasts an outdoor pool, a full-service spa with a hot tub and various treatment options, including Swedish and hot stone massages. Guests can enjoy complimentary breakfast and convenient electric car charging stations. With its prime location near the historical district and nearby golf courses, this hotel perfectly combines relaxation and exploration in Healdsburg. - **Nearby attractions:** Healdsburg Plaza - 0.2 km, Healdsburg Center for the Arts - 0.3 km, Healdsburg Museum - 0.4 km [Healdsburg Inn on the Plaza, A Four Sisters Inn](https://www.expedia.ca/Healdsburg-Hotels-Healdsburg-Inn-On-The-Plaza.h2937684.Hotel-Information) - **Why it's great for a luxury retreat:** The Healdsburg Inn on the Plaza offers luxury and charm, rated highly with a guest review rating of 9.0. This boutique hotel features premium bedding and inviting fireplaces, creating a warm and sophisticated atmosphere. Guests will appreciate the attentive concierge service, ensuring their stay is both seamless and enjoyable while being steps away from the shopping district. - **Other amenities:** In addition to its luxurious accommodations, the inn provides complimentary breakfast and daily housekeeping. Guests can enjoy access to nearby golf courses and biking trails, perfect for those looking to explore the outdoors. With free parking and a cozy balcony or patio available for most rooms, the inn offers a delightful retreat in the heart of Healdsburg. - **Nearby attractions:** Healdsburg Plaza - 0 km, Healdsburg Center for the Arts - 0.2 km, Healdsburg Museum - 0.2 km [Camellia Inn](https://www.expedia.ca/Healdsburg-Hotels-Camellia-Inn.h19772287.Hotel-Information) - **Why it's great for a luxury retreat:** Camellia Inn is a charming luxury getaway with a remarkable review rating of 9.0, perfect for travelers. The inn features premium bedding and elegant bathrobes, ensuring a comfortable and indulgent stay. Guests can enjoy complimentary breakfasts and the opportunity to explore the onsite winery tasting room, creating a truly memorable experience in the heart of wine country. - **Other amenities:** Beyond its luxurious offerings, Camellia Inn boasts a serene outdoor pool and a tranquil garden for relaxation. The full-service spa provides a range of treatments, including massages and aromatherapy sessions. Guests can also take advantage of free self-parking and nearby hiking and biking trails, making it easy to explore the stunning surroundings of Healdsburg. - **Nearby attractions:** Healdsburg Plaza - 0.4 km, Healdsburg Center for the Arts - 0.2 km, Healdsburg Museum - 0.3 km ## Top Healdsburg Hotel Reviews ![Hotel Healdsburg](//images.trvl-media.com/lodging/1000000/790000/786900/786805/9d93bedd_y.jpg) ### Hotel Healdsburg 10/10 Excellent "parking lot under rooms so you hear beep beep from the key fobs, bar next door loud boom boom music and couldn't sleep until 1 am " [](https://expedia.ca/Healdsburg-Hotels-Hotel-Healdsburg.h786805.Hotel-Information) ![Fairview Inn and Suites](//images.trvl-media.com/lodging/2000000/1120000/1111500/1111427/55aee5ca_y.jpg) ### Fairview Inn and Suites 10/10 Excellent "Very Clean and Modern. Would definitely stay again." [](https://expedia.ca/Healdsburg-Hotels-Fairview-Inn-And-Suites.h1111427.Hotel-Information) ![H2Hotel](//images.trvl-media.com/lodging/4000000/3620000/3618400/3618334/92a67a3e_y.jpg) ### H2Hotel 10/10 Excellent "I enjoyed the ambiance, friendliness and cleanliness. Everyone seemed to be happy" [](https://expedia.ca/Healdsburg-Hotels-H2hotel.h3618334.Hotel-Information) ![Best Western Dry Creek Inn](//images.trvl-media.com/lodging/1000000/20000/19400/19399/f85bb490_y.jpg) ### Best Western Dry Creek Inn 10/10 Excellent "Nice job updating the property " [](https://expedia.ca/Healdsburg-Hotels-Best-Western-Dry-Creek-Inn.h19399.Hotel-Information) ![Healdsburg Inn on the Plaza, A Four Sisters Inn](//images.trvl-media.com/lodging/3000000/2940000/2937700/2937684/aab76a75_y.jpg) ### Healdsburg Inn on the Plaza, A Four Sisters Inn 10/10 Excellent "Healdsburg Inn in a beautiful place to stay. The staff was so helpful and wonderful to talk to about the city. We have stayed there a few times and will be back. Being right on the plaza make it very easy to check everything out and stagger back after some wine tasting." [](https://expedia.ca/Healdsburg-Hotels-Healdsburg-Inn-On-The-Plaza.h2937684.Hotel-Information) ![27 North](//images.trvl-media.com/lodging/2000000/1640000/1639800/1639752/808f26c5_y.jpg) ### 27 North 10/10 Excellent "We enjoyed our stay. Very welcoming and professional staff. Rooms were beautiful and clean. " [](https://expedia.ca/Healdsburg-Hotels-Hotel-Les-Mars.h1639752.Hotel-Information) ![The Madrona](//images.trvl-media.com/lodging/1000000/460000/451700/451693/ac03bc94_y.jpg) ### The Madrona 10/10 Excellent "My stay at The Madrona was nothing short of beautiful, relaxing and calming. The property itself is stunning, quiet and soothing and my room was more than I could have asked for. I was only staying for one night so I had dinner there and it was delicious. I wish I could have stayed longer. The staff is friendly and welcoming and I will be returning as soon as I possibly can. It’s a perfect place to relax. " [](https://expedia.ca/Healdsburg-Hotels-The-Madrona.h451693.Hotel-Information) ![Hotel Vinea, a Travelodge by Wyndham](//images.trvl-media.com/lodging/1000000/130000/126600/126590/b9d4555c_y.jpg) ### Hotel Vinea, a Travelodge by Wyndham 10/10 Excellent "I want to say it’s bad so it won’t be booked up the next time I want to stay here, but I can’t. What a great little hotel with awesome staff and a breakfast that included a few GF items. I will definitely stay here again soon! For reference, I’m Marriott Platinum for Life so I was a tad worried about booking here…but I was extremely pleased with the comfort, location and overall quality of this cute little place. " [](https://expedia.ca/Healdsburg-Hotels-Hotel-Vinea.h126590.Hotel-Information) ![Calderwood Inn](//images.trvl-media.com/lodging/7000000/6950000/6948800/6948795/a77aa9d4_y.jpg) ### Calderwood Inn 10/10 Excellent "Only one complaint. The bed was stiff." [](https://expedia.ca/Healdsburg-Hotels-Calderwood-Inn.h6948795.Hotel-Information) ## Frequently asked questions ### Are you searching for a great accommodation for your luxury trip to Healdsburg? > During your visit, you might want to enjoy the wineries and shopping which Healdsburg is known for. ### What's the best luxury hotel in Healdsburg? > [Montage Healdsburg](https://www.expedia.ca/Healdsburg-Hotels-Montage-Healdsburg.h57173926.Hotel-Information) is a luxury hotel with 2 restaurants and 2 bars, and it's a popular choice for Expedia travelers looking for an elegant place to stay. [The Ruse](https://www.expedia.ca/Healdsburg-Hotels-The-Ruse.h89177143.Hotel-Information) and [27 North](https://www.expedia.ca/Healdsburg-Hotels-Hotel-Les-Mars.h1639752.Hotel-Information) are other upscale choices for your trip. ### When can I expect good weather in Healdsburg? > Planning for the weather is an important factor for making your trip to Healdsburg a success, especially when you're splurging. The hottest months are usually July and August with an average temp of 69°F, while the coldest months are December and January with an average of 49°F. Average annual precipitation for Healdsburg is 31 inches. ### What's there to see and do in Healdsburg? > Experience all that Healdsburg has to offer when you visit Healdsburg Plaza, Jordan Vineyard & Winery, and SingleThread Farm at Dry Creek. 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