Title: Healdsburg Villas | 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) ![Dry Creek Vineyard featuring flowers and a park](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/215000/215995-Healdsburg-Sc.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Healdsburg Villa Rentals ![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 prices for these dates 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&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Healdsburg Villas ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33570000/33564100/33564030/19ea979e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/34000000/33570000/33564100/33564030/w1218h899x1y1-921cc419.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33570000/33564100/33564030/w1280h857x0y0-16a6b8ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor banquet area](https://images.trvl-media.com/lodging/34000000/33570000/33564100/33564030/896cbd13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Secluded Vineyard Estate Healdsburg Healdsburg 9.8/10 Exceptional (124) "Our group had the best time! Such a lovely property with ample space to gather together but also relax. We really enjoyed hanging by the pool and enjoying a nice dinner outside. Kitchen was well stocked with plates, utensils, spices, glassware, etc. Having two dishwashers for a large group was really nice as well.The house is a quick drive into town but feels like you are in your own little world!We're already thinking about the next time we can come back up & stay again! " [](https://www.expedia.ca/Healdsburg-Hotels-Close-To-Plaza15-Acre-EstateSwimming-Pool-And-Bocce-Ball.h33564030.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73980000/73977100/73977002/80449bd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73980000/73977100/73977002/ff781ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/74000000/73980000/73977100/73977002/db75e46a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73980000/73977100/73977002/2717be85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stay surrounded by Fitch Mountain Park and Open Space Preserve. Healdsburg 9.4/10 Exceptional (26) "Very clean and comfortable stay. " [](https://www.expedia.ca/Healdsburg-Hotels-Stay-Surrounded-By-Fitch-Mountain-Park-And-Open-Space-Preserve.h73977002.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113280000/113277100/113277022/0829a7c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/114000000/113280000/113277100/113277022/w1440h960x0y0-629000ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113280000/113277100/113277022/594be5f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/114000000/113280000/113277100/113277022/781cb9f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa Terra Bella, by Vinifera Homes Windsor 10/10 Exceptional (5) "Great house, extremely spacious and well cared for. It was a pleasure to be there. " [](https://www.expedia.ca/Windsor-Hotels-Villa-Terra-Bella-A-Tranquil-Windsor-Escape-W-Natural-Stone-Pool-Court.h113277022.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34430000/34428600/34428547/fa1139cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/35000000/34430000/34428600/34428547/f0543bbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34430000/34428600/34428547/c2517a37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/35000000/34430000/34428600/34428547/20894428.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Entire Wine Country Resort Villa #Pool-Spa-Tennis-Wine-Dine# Healdsburg 10/10 Exceptional (19) "The home and grounds had everything we needed, and then some. The home is close to several great wineries and restaurants. Would highly recommend!" [](https://www.expedia.ca/Windsor-Hotels-Entire-Wine-Country-Resort-Villa-Pool-Spa-Tennis-Wine-Dine.h34428547.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/37000000/36660000/36651100/36651099/47599e0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, printers](https://images.trvl-media.com/lodging/37000000/36660000/36651100/36651099/36c0db42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/37000000/36660000/36651100/36651099/5988206b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/37000000/36660000/36651100/36651099/8e4a572f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Organic Ranch Fabulous for Groups with Farm Healdsburg 10/10 Exceptional (27) "The property, home and experiences were perfect for our family vacation." [](https://www.expedia.ca/Healdsburg-Hotels-Private-Luxury-Ranch-W-Unforgettable-Experiences.h36651099.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=2025-10-12&endDate=2025-10-13®ionId=8322&adults=2&lodging=VILLA&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FHealdsburg-Villas.d8322-aaVillas.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHealdsburg-Villas.d8322-aaVillas.Travel-Guide-Accommodation) ## 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) ![The Lodge at Healdsburg, Tapestry Collection by Hilton](//images.trvl-media.com/lodging/84000000/83700000/83691500/83691429/540cf294_y.jpg) ### The Lodge at Healdsburg, Tapestry Collection by Hilton 10/10 Excellent "great place to stay, nice common areas" [](https://expedia.ca/Healdsburg-Hotels-The-Lodge-At-Healdsburg.h83691429.Hotel-Information) ![Appellation Healdsburg](//images.trvl-media.com/lodging/119000000/118740000/118739000/118738917/3a9c426d_y.jpg) ### Appellation Healdsburg 10/10 Excellent "We had the opportunity to stay within two weeks of the opening. It has a wonderful vibe, the breakfast was outstanding (especially the gluten free blueberry muffins - one in our party has celiac disease), and the staff courteous. We would stay again." [](https://expedia.ca/Healdsburg-Hotels-Appellation-Healdsburg.h118738917.Hotel-Information) ![The Ruse](//images.trvl-media.com/lodging/90000000/89180000/89177200/89177143/5b83d9ce_y.jpg) ### The Ruse 10/10 Excellent "Beautiful property, outstanding staff & incredible breakfast!" [](https://expedia.ca/Healdsburg-Hotels-The-Ruse.h89177143.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) ![Hotel Trio Healdsburg](//images.trvl-media.com/lodging/24000000/23260000/23251300/23251292/b5cf89bc_y.jpg) ### Hotel Trio Healdsburg 10/10 Excellent "Everything was amazing here we happened to make the thursday tasting in the lobby staff was very helpful. The room comes with self help wine station credits we didnt get to try but breakfast was very nice. We were assigned to an ADA room very spacious the only thing was water pressure and temperature of the shower, not the warmest shower probably because we were on top floor. Overall still great we will definitely come back." [](https://expedia.ca/Healdsburg-Hotels-Hotel-Trio-Healdsburg.h23251292.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) ![Montage Healdsburg](//images.trvl-media.com/lodging/58000000/57180000/57174000/57173926/a19e59f7_y.jpg) ### Montage Healdsburg 10/10 Excellent "We celebrated our 30th wedding anniversary and stayed at Montage Healdsburg, a very nice property for sure!! Staff was welcoming and very courteous. My wife & I enjoyed our stay and highly recommend!!" [](https://expedia.ca/Healdsburg-Hotels-Montage-Healdsburg.h57173926.Hotel-Information) ## Find out more about Healdsburg ## Healdsburg Villas information | Number of reviews | 171 | | --- | --- | | Accommodation | 5 Villas | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [1 Star Hotels in Foss Creek Pathway](https://www.expedia.ca/1Star-Foss-Creek-Pathway-Hotels.s10-0-d832563055564120064.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Foss Creek Pathway](https://www.expedia.ca/4Star-Foss-Creek-Pathway-Hotels.s40-0-d832563055564120064.Travel-Guide-Filter-Hotels) - [Aparthotels in Alexander Valley](https://www.expedia.ca/Alexander-Valley-Apart-Hotels.d736344212904407040-aaApartHotels.Travel-Guide-Accommodation) - [Chalets in Alexander Valley](https://www.expedia.ca/Alexander-Valley-Chalets.d736344212904407040-aaChalets.Travel-Guide-Accommodation) - [Condo Rentals in Alexander Valley](https://www.expedia.ca/Alexander-Valley-Condos.d736344212904407040-aaCondos.Travel-Guide-Accommodation) - 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[Flights from Windsor](https://www.expedia.ca/lp/flights/9542/flights-from-windsor) - [Dry Creek Vineyard](https://www.expedia.ca/Dry-Creek-Vineyard-Healdsburg.d6240812.Vacation-Attraction) - [Visit Foss Creek Pathway](https://www.expedia.ca/Foss-Creek-Pathway.dx832563055564120064) - [Francis Ford Coppola Winery](https://www.expedia.ca/Francis-Ford-Coppola-Winery-Geyserville.d553248621532640800.Vacation-Attraction) - [Mazzocco Winery](https://www.expedia.ca/Mazzocco-Winery-Healdsburg.d6324652.Vacation-Attraction) - [Soda Rock Winery](https://www.expedia.ca/Soda-Rock-Winery-Healdsburg.d6324674.Vacation-Attraction) - [Windsor Oaks Vineyards](https://www.expedia.ca/Windsor-Oaks-Vineyards-Windsor.d6327443.Vacation-Attraction) - [Windsor Vacations](https://www.expedia.ca/Windsor.d9542.Destination-Travel-Guides) - [Visit Windsor](https://www.expedia.ca/Windsor.dx9542) - [Car rentals near Matrix Winery](https://www.expedia.ca/Car-Rentals-In-Matrix-Winery.d6324682.Car-Rental-Guide) - [Car rental Windsor](https://www.expedia.ca/Car-Rentals-In-Windsor.d9542.Car-Rental-Guide) - 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