Title: Healdsburg Vacation Home Rentals from CA $292: 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 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) # Healdsburg Vacation Rentals ![](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 [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=8322&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Healdsburg Vacation Homes ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111910000/111903100/111903019/68f52a9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/112000000/111910000/111903100/111903019/b9e31119.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/112000000/111910000/111903100/111903019/1b0babd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111910000/111903100/111903019/da7e8eea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vineyard Oasis: Luxury Home in the Heart of Sonoma. Healdsburg 10/10 Exceptional (7) "We had a great time!The house was perfect for our needs!" CA $181 CA $475 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Santa-Rosa-Hotels-Vineyard-Oasis-Luxury-Home-In-The-Heart-Of-Sonoma.h111903019.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/111000000/110950000/110941300/110941239/369a8941.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/111000000/110950000/110941300/110941239/11f87e8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110950000/110941300/110941239/b5c48e96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/111000000/110950000/110941300/110941239/b4681054.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW Gurneville Backyard Oasis + Spa + Firepit + Dog Friendly + Wi-Fi Guerneville 10/10 Exceptional (1) "The cabin is thoughtfully and beautifully appointed. Perfectly cozy for our group of three (two adults, one tween) and a dog. We really enjoyed our stay. Very close to a lot of fun activities and peaceful. Host Mike was awesome and communicative." CA $221 CA $570 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Guerneville-Hotels-NEW-Gurneville-Backyard-Oasis-Spa-Firepit-Dog-Friendly-Wi-Fi.h110941239.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/101000000/101000000/100995400/100995386/f38842a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/101000000/101000000/100995400/100995386/77ee18dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/101000000/100995400/100995386/11c6dd8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/101000000/100995400/100995386/36907a6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Walk to Russian River - Casa Del Rio - Unit A Forestville 9.2/10 Wonderful (37) "Bright and cheerful home, 1 minute walk to the river. Our family had such a great trip. Thanks!" CA $154 CA $547 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Forestville-Hotels-Walk-To-Russian-River-Casa-Del-Rio-Unit-A.h100995386.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/64000000/63170000/63163000/63162961/5d409705.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/64000000/63170000/63163000/63162961/00d89a28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/64000000/63170000/63163000/63162961/002973d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/64000000/63170000/63163000/63162961/6854334d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winemaker's Delight: 3BD/3BA Russian River Valley Northwest Santa Rosa 9.8/10 Exceptional (69) "Excellent location to Sonoma Valley, good size rooms, quiet location, very comfy home." CA $303 CA $703 total includes taxes & fees Oct 21 - Oct 22 [](https://www.expedia.ca/Santa-Rosa-Hotels-Winemakers-Delight-3BD3BA-Russian-River-Valley.h63162961.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/97000000/96830000/96826500/96826435/42b00b7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/97000000/96830000/96826500/96826435/69210f26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/97000000/96830000/96826500/96826435/eb86b88b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96830000/96826500/96826435/987e7a4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Puccioni Paradise | A Wine Country Escape Healdsburg 10/10 Exceptional (2) "Was a great stay. Very much appreciated the location, amenities and communication." CA $274 CA $971 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Healdsburg-Hotels-Secluded-Retreat-Only-10-Minutes-From-The-Healdsburg-Plaza.h96826435.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/35000000/34120000/34110800/34110780/4fe30ec6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34120000/34110800/34110780/b3eef42f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34120000/34110800/34110780/w445h350x0y0-f448777c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, music library](https://images.trvl-media.com/lodging/35000000/34120000/34110800/34110780/de315663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 𝑳𝒖𝒙𝒖𝒓𝒚 𝑷𝒓𝒊𝒗𝒂𝒕𝒆 𝑬𝒔𝒕𝒂𝒕𝒆 𝒂𝒕 𝒁𝒐𝒆𝒍𝒍𝒂 𝑽𝒊𝒏𝒆𝒚𝒂𝒓𝒅.𝑷𝑶𝑶𝑳&𝑺𝑷𝑨!𝑮𝑨𝑴𝑬𝑹𝑶𝑶𝑴! Healdsburg 9.6/10 Exceptional (62) "Great location next to some awesome wineries. Great place to relax after a day of wine tasting!" CA $2,011 CA $2,982 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Healdsburg-Hotels-Luxury-Private-Estate-At-Zoella-VineyardPOOLSPAGAMEROOM.h34110780.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/100000000/99240000/99230200/99230158/e904b73a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99240000/99230200/99230158/dbddd4a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99240000/99230200/99230158/f7c1ac80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/100000000/99240000/99230200/99230158/16654dfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Farpoint: Heated Infinity Pool, Mountain Views Santa Rosa 9.8/10 Exceptional (7) "Great location with lots of amenities. Very calming atmosphere. Very attentive staff. Can’t wait to go back." CA $672 CA $1,378 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Santa-Rosa-Hotels-Farpoint-Heated-Infinity-Pool.h99230158.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/98000000/97080000/97078500/97078495/3c2d3a8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/98000000/97080000/97078500/97078495/0928c2ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97080000/97078500/97078495/w2999h1999x1y1-c4637e37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/98000000/97080000/97078500/97078495/w3000h1999x0y1-14631996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dragonfly Healdsburg | A Wine Country Escape Healdsburg 10/10 Exceptional (6) "The pictures didn’t do justice to how wonderful the property is. The outdoor space is amazing. Just wish the weather was warmer to enjoy it more. We will definitely be booking another stay here. Communication with property owner was responsive and helpful. " CA $815 CA $1,839 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Healdsburg-Hotels-The-Dragonfly-Healdsburg-Oasis-With-Infinity-Pool.h97078495.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/110000000/109800000/109790500/109790438/e518274e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109800000/109790500/109790438/f9a63ef3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/110000000/109800000/109790500/109790438/9262173b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109800000/109790500/109790438/f9fe9b51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Estate Awaits: Your Ultimate Vineyard Escape Windsor CA $909 CA $1,766 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Windsor-Hotels-Luxury-Estate-Awaits-Your-Ultimate-Vineyard-Escape.h109790438.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/103000000/102860000/102856900/102856893/94f1299f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102860000/102856900/102856893/b0cd49fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102860000/102856900/102856893/962d1456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/103000000/102860000/102856900/102856893/c723dab0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bright and modern - Water views - Close to beach Dillon Beach 10/10 Exceptional (15) "Our stay at Kellie's Dillon Beach home was so very comfortable and had everything we needed. Super comfortable bed, awesome kitchen and loved the patios!" CA $241 CA $664 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Dillon-Beach-Hotels-Bright-And-Modern-Water-Views-Close-To-Beach.h102856893.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/113000000/112770000/112768500/112768479/131aac38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/113000000/112770000/112768500/112768479/16fc075a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112770000/112768500/112768479/4102bb3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112770000/112768500/112768479/44197490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lovely Russian River Bungalow-2BR 1 BA New Remodel Forestville 10/10 Exceptional (3) "Darling small bungalow style home that was nicely decorated and comfortable. Bonus outdoor patio that we really enjoyed. Good location. Road to home had some twist and turns. Just be cautious and drive slowly. Definitely recommend! We loved our stay here." CA $179 CA $569 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Forestville-Hotels-Lovely-Russian-River-Bungalow-2BR-1-BA-New-Remodel.h112768479.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/119000000/118950000/118942400/118942367/0e78fe39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/119000000/118950000/118942400/118942367/da41834a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118950000/118942400/118942367/b093a976.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118950000/118942400/118942367/9971a214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Lake Escape 2-bedroom house with WiFi, AC in delightful Clearlake Clearlake 10/10 Exceptional (1) "Sarah was very helpful and responded to my enqueries very promptly. " CA $179 CA $360 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Clearlake-Hotels-Cozy-Lake-Escape-2-Bedroom-House-With-WiFi.h118942367.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/94000000/93010000/93000100/93000043/w1280h852x0y1-f46135d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/94000000/93010000/93000100/93000043/w1280h852x0y1-7bfaeb85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/94000000/93010000/93000100/93000043/c5554be3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/94000000/93010000/93000100/93000043/2422fa68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Glen Ellen Retreat #1 Hot Tub and King Beds Glen Ellen 10/10 Exceptional (72) "Extremely nice property in lovely quaint Glen Ellen." CA $254 CA $604 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Glen-Ellen-Hotels-Glen-Ellen-Retreat-1-King-Beds.h93000043.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/79000000/78540000/78538200/78538149/e92d608a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/79000000/78540000/78538200/78538149/83e2e758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/79000000/78540000/78538200/78538149/05e1da79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/79000000/78540000/78538200/78538149/12fc56ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Hidden Wine Country Gem Upstairs Unit Scenic Brush Creek 9.6/10 Exceptional (20) "We enjoyed our stay and would certainly use this rental again if we're ever in the area. " CA $251 CA $492 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Santa-Rosa-Hotels-2-Hidden-Wine-Country-Gem-Upstairs-Unit.h78538149.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/96000000/95820000/95819000/95818932/2d45ff45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/96000000/95820000/95819000/95818932/w1024h681x0y0-eedc090b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95820000/95819000/95818932/w1024h678x0y3-813a6dba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, computer monitors](https://images.trvl-media.com/lodging/96000000/95820000/95819000/95818932/w1024h679x0y2-5543a4db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cobb Mountain Chalet Main For Cobb 9.6/10 Exceptional (14) "A always a great stay this is my fourth stay." CA $136 CA $292 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Kelseyville-Hotels-Cobb-Mountain-Chalet-Main-For.h95818932.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/107000000/106830000/106823900/106823878/ea1f04ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/107000000/106830000/106823900/106823878/141330f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106830000/106823900/106823878/9fb14866.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106830000/106823900/106823878/ffe521d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy cabin deep in the redwoods / WiFi & Hot Tub Guerneville 10/10 Exceptional (1) "We stayed the weekend with friends at this beautiful hideaway in the woods and had a wonderful time. The house was spotless, the jacuzzi was perfect, the lighting was fun and ethereal, the fireplace was cozy, tv was easy to operate and had Netflix (thanks!). The beds are on the soft side, and curtains are sheer, which didn’t bother us, but that might be hard for some folks. We had a great time! Thank you so much!!!" CA $182 CA $333 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Guerneville-Hotels-Cozy-Cabin-Deep-In-The-Redwoods-WiFi-Hot-Tub.h106823878.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/38000000/37620000/37620000/37619909/95a4f781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/38000000/37620000/37620000/37619909/w1280h852x0y1-641c34b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37620000/37620000/37619909/w1279h852x1y1-268bd65d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/38000000/37620000/37620000/37619909/w1280h852x0y1-9fa7a420.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Glen Ellen Retreat #2 King Beds Glen Ellen 10/10 Exceptional (153) "Had lovely stay. Home was cozy, clean, and close to everything. We would love to stay again :)" CA $210 CA $547 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Glen-Ellen-Hotels-Glen-Ellen-Retreat-2-King-Beds.h37619909.Hotel-Information) ![House, 3 Bedrooms | Property grounds](https://images.trvl-media.com/lodging/108000000/107980000/107978600/107978580/b4639236.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 3 Bedrooms | Interior](https://images.trvl-media.com/lodging/108000000/107980000/107978600/107978580/0a2dd277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 3 Bedrooms | Living area](https://images.trvl-media.com/lodging/108000000/107980000/107978600/107978580/ddee8f39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 3 Bedrooms | Private kitchen](https://images.trvl-media.com/lodging/108000000/107980000/107978600/107978580/df062f50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakeside Retreat With Private Boat Ramp 3 Bedroom Home by RedAwning Clearlake CA $212 CA $684 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Clearlake-Hotels-Lakeside-Retreat-With-Private-Boat-Ramp-3-Bedroom-Home.h107978580.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107450000/107449100/107449045/355f0309.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/108000000/107450000/107449100/107449045/afef7656.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107450000/107449100/107449045/1cd51066.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/108000000/107450000/107449100/107449045/1150ebe4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Russian River Retreat with Hot Tub, BBQ, & Deck Forestville 10/10 Exceptional (3) "We had a great time visiting the Russian River Valley. This property was as advertised and very comfortable. We had plenty of space and really enjoyed the kitchen, back deck, and hot tub. We had a toddler with us and found the place to be relatively toddler friendly, just had to hide some breakables and barricade the stairs, but she had a great time! Our only complaint was the level of road noise, but that probably comes with any property that is along River Road. " CA $221 CA $632 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Forestville-Hotels-Russian-River-Retreat-With-Hot-Tub.h107449045.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105360000/105356500/105356471/5b7aba8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105360000/105356500/105356471/6551c4de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105360000/105356500/105356471/adba7e9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105360000/105356500/105356471/5042f25b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful, charming, cottage in wine country. Beautiful yard! Sebastopol 9.8/10 Exceptional (7) "Kitchen overhead light broken, kitchen sink sprayer broken, window lock broken, complicated unfamiliar coffee maker with no instructions. " CA $194 CA $473 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Sebastopol-Hotels-Peaceful.h105356471.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=2025-10-27&endDate=2025-10-28®ionId=8322&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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-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 ![The Ruse](//images.trvl-media.com/lodging/90000000/89180000/89177200/89177143/5b83d9ce_y.jpg) ### The Ruse 10/10 Excellent "Comfortable room adjacent to main building. Gourmet breakfast. Parking at our front door. Free charger for EV on property. Helpful staff. Short drive to excellent restaurants and shopping." [](https://expedia.ca/Healdsburg-Hotels-The-Ruse.h89177143.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 "It's nice to be able to step out of your room and take a short walk to the comfortable outdoor hot tub but still be within the confines of the hotel's private space." [](https://expedia.ca/Healdsburg-Hotels-The-Lodge-At-Healdsburg.h83691429.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 "Great place to stay" [](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 "Absolutely stunning!!! " [](https://expedia.ca/Healdsburg-Hotels-Montage-Healdsburg.h57173926.Hotel-Information) ![Appellation Healdsburg](//images.trvl-media.com/lodging/119000000/118740000/118739000/118738917/c0eb31c7_y.jpg) ### Appellation Healdsburg 10/10 Excellent "What a great new property! Welcoming staff, very clean and fresh facilities. Bar staff could be friendlier and mire helpful. Valet, check in and restaurant staff very friendly." [](https://expedia.ca/Healdsburg-Hotels-Appellation-Healdsburg.h118738917.Hotel-Information) ![Camellia Inn](//images.trvl-media.com/lodging/20000000/19780000/19772300/19772287/902be535_y.jpg) ### Camellia Inn 10/10 Excellent "Quiet, charming, terrifically located inn within easy walking distance of Healdsburg's many downtown attractions." [](https://expedia.ca/Healdsburg-Hotels-Camellia-Inn.h19772287.Hotel-Information) ![Hotel Healdsburg](//images.trvl-media.com/lodging/1000000/790000/786900/786805/9d93bedd_y.jpg) ### Hotel Healdsburg 10/10 Excellent "Lovely hotel in the heart of Healdsburg. Wonderful stay. " [](https://expedia.ca/Healdsburg-Hotels-Hotel-Healdsburg.h786805.Hotel-Information) ![Hotel Trio Healdsburg](//images.trvl-media.com/lodging/24000000/23260000/23251300/23251292/b5cf89bc_y.jpg) ### Hotel Trio Healdsburg 10/10 Excellent "The room was perfect. Two rooms is so nice. Here for a wedding, bed super comfy, soft pillows. Nice decor. Nice little kitchen. LOVE coffee and water all day, needed it. Cute outside area. Great breakfast. All in all a great visit !" [](https://expedia.ca/Healdsburg-Hotels-Hotel-Trio-Healdsburg.h23251292.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 "good place to stay close to vineyards and restaurants " [](https://expedia.ca/Healdsburg-Hotels-Hotel-Vinea.h126590.Hotel-Information) ## Find out more about Healdsburg ## Healdsburg Vacation Homes information | Number of reviews | 437 | | --- | --- | | Accommodation | 246 Vacation Homes | | Lowest Price | CA $292 | | Highest Price | CA $2,982 | ## 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) - 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