Title: Healdsburg Vacation Home Rentals from CA $273: Search Top Private Vacation Homes for Rent | 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 showing signage](https://images.trvl-media.com/place/6240812/8658489b-fa3e-4a38-b1bf-af5bdb5d9bd5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/6240812/8658489b-fa3e-4a38-b1bf-af5bdb5d9bd5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](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 [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. 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[Book now](https://expedia.ca/deals?rfrr=AA_SPRING_PROMO_8322) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Healdsburg%2C+California%2C+United+States+of+America®ionId=8322&latLong=38.610466%2C-122.869163&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Healdsburg%2C+California%2C+United+States+of+America®ionId=8322&latLong=38.610466%2C-122.869163&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=APART_HOTEL) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Healdsburg%2C+California%2C+United+States+of+America®ionId=8322&latLong=38.610466%2C-122.869163&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=COTTAGE) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Healdsburg%2C+California%2C+United+States+of+America®ionId=8322&latLong=38.610466%2C-122.869163&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=APARTMENT) Villas [](https://www.expedia.ca/Hotel-Search?destination=Healdsburg%2C+California%2C+United+States+of+America®ionId=8322&latLong=38.610466%2C-122.869163&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=VILLA) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Healdsburg%2C+California%2C+United+States+of+America®ionId=8322&latLong=38.610466%2C-122.869163&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=CABIN) Condos [](https://www.expedia.ca/Hotel-Search?destination=Healdsburg%2C+California%2C+United+States+of+America®ionId=8322&latLong=38.610466%2C-122.869163&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=CONDO) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Healdsburg%2C+California%2C+United+States+of+America®ionId=8322&latLong=38.610466%2C-122.869163&adults=2&startDate=2026-05-25&d1=2026-05-25&endDate=2026-05-28&d2=2026-05-28&lodging=CHALET) ![](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-Private-Vacation-Homes.d8322-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHealdsburg-Private-Vacation-Homes.d8322-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Healdsburg Hotel Reviews ![Best Western Dry Creek Inn](https://images.trvl-media.com/lodging/1000000/20000/19400/19399/5ab8ae96_y.jpg) ### Best Western Dry Creek Inn 10/10 Excellent "We had a very good stay at Dry Creek Inn! The rooms were clean and the staff was helpful with our questions and friendly. It's a great location and we have stayed here several times. We appreciate the discount at the restaurant next to the Inn as well. We come out every couple of years and will check back with your property again. Glad you are there!" [](https://expedia.ca/Healdsburg-Hotels-Dry-Creek-Inn-MOD-Collection-By-Sonesta.h19399.Hotel-Information) ![Fairview Inn and Suites](https://images.trvl-media.com/lodging/2000000/1120000/1111500/1111427/55aee5ca_y.jpg) ### Fairview Inn and Suites 10/10 Excellent "The room was spotless and the bed was extremely comfortable. Staff was very friendly and accommodating. " [](https://expedia.ca/Healdsburg-Hotels-Fairview-Inn-And-Suites.h1111427.Hotel-Information) ![Appellation Healdsburg](https://images.trvl-media.com/lodging/119000000/118740000/118739000/118738917/4fc40d21_y.jpg) ### Appellation Healdsburg 10/10 Excellent "Beautiful property " [](https://expedia.ca/Healdsburg-Hotels-Appellation-Healdsburg.h118738917.Hotel-Information) ![The Madrona](https://images.trvl-media.com/lodging/1000000/460000/451700/451693/ac03bc94_y.jpg) ### The Madrona 10/10 Excellent "What a lovely place. Great staff, grounds and amenities. We will be back!!" [](https://expedia.ca/Healdsburg-Hotels-The-Madrona.h451693.Hotel-Information) ![Calderwood Inn](https://images.trvl-media.com/lodging/7000000/6950000/6948800/6948795/a77aa9d4_y.jpg) ### Calderwood Inn 10/10 Excellent "The place has a historical charm. The furniture and amenities are a bit aged, but the overall experience is great. Love the breakfast in the beautiful dining room." [](https://expedia.ca/Healdsburg-Hotels-Calderwood-Inn.h6948795.Hotel-Information) ![Cottages at Little Saint](https://images.trvl-media.com/lodging/31000000/30060000/30058500/30058405/9ce26d13_y.jpg) ### Cottages at Little Saint 10/10 Excellent "Beautiful property and super comfortable beds." [](https://expedia.ca/Healdsburg-Hotels-Cottages-At-Healdsburg.h30058405.Hotel-Information) ![Hotel Healdsburg](https://images.trvl-media.com/lodging/1000000/790000/786900/786805/9d93bedd_y.jpg) ### Hotel Healdsburg 10/10 Excellent "Great hotel! " [](https://expedia.ca/Healdsburg-Hotels-Hotel-Healdsburg.h786805.Hotel-Information) ![The Lodge at Healdsburg, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/84000000/83700000/83691500/83691429/540cf294_y.jpg) ### The Lodge at Healdsburg, Tapestry Collection by Hilton 10/10 Excellent "amazing. 10/10" [](https://expedia.ca/Healdsburg-Hotels-The-Lodge-At-Healdsburg.h83691429.Hotel-Information) ![Hotel Trio Healdsburg](https://images.trvl-media.com/lodging/24000000/23260000/23251300/23251292/b5cf89bc_y.jpg) ### Hotel Trio Healdsburg 10/10 Excellent "Friendly staff, clean and fresh rooms" [](https://expedia.ca/Healdsburg-Hotels-Hotel-Trio-Healdsburg.h23251292.Hotel-Information) ## Find out more about Healdsburg ## Healdsburg Vacation Homes information | Number of reviews | 434 | | ----------------- | ------------------ | | Accommodation | 231 Vacation Homes | | Lowest Price | CA $273 | | Highest Price | CA $2,448 | ## Explore a world of travel with Expedia - Lodging - 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