Title: Windsor Guest Houses from CA $258 | Expedia.ca [Windsor Travel Guide](https://expedia.ca/Windsor.dx9542)[Hotels in Windsor](https://expedia.ca/Windsor-Hotels.d9542.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.ca/Windsor-Vacation-Rentals.d9542.Travel-Guide-VacationRentals)[Things to do in Windsor](https://expedia.ca/Things-To-Do-In-Windsor.d9542.Travel-Guide-Activities)[Windsor Car Rentals](https://expedia.ca/Car-Rentals-In-Windsor.d9542.Car-Rental-Guide)[Windsor Vacation Packages](https://expedia.ca/Windsor.d9542.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/8198ad1ad279b2f1094cf055187bc546.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Jennifer Hill # Search Guest Houses in Windsor from CA $258 ![](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 Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=9542&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=9542&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=9542&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=9542&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Windsor Guest Houses ![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) ![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 | Terrace/patio](https://images.trvl-media.com/lodging/7000000/6950000/6948800/6948795/96f03827.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 (243) "Great front porch sitting area. Cookies. Wine in living room. " CA $223 CA $258 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Healdsburg-Hotels-Calderwood-Inn.h6948795.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/8000000/7330000/7326600/7326527/0132d592.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/8000000/7330000/7326600/7326527/4a1aa170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7330000/7326600/7326527/ff6e1485.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/8000000/7330000/7326600/7326527/48c0432a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vineyard Country Inn St. Helena 9.2/10 Wonderful (708) "Great place with very friendly staff." CA $303 CA $349 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/St-Helena-Hotels-Vineyard-Country-Inn.h7326527.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/9000000/8690000/8680700/8680661/3e3f8505.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/9000000/8690000/8680700/8680661/w460h290x5y5-cc710333.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/9000000/8690000/8680700/8680661/w461h291x5y4-6f825f83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/9000000/8690000/8680700/8680661/6ff5f8ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Guerneville Lodge Guerneville 8.4/10 Very good (325) "Al was great to work with, very flexible and accommodating. Sweet room, comfy bed and amazing library!" CA $349 CA $398 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Guerneville-Hotels-Guerneville-Lodge.h8680661.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99400000/99391600/99391569/a170c2d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/100000000/99400000/99391600/99391569/f0f0b083.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/100000000/99400000/99391600/99391569/f9f32817.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99400000/99391600/99391569/5b57f509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quiet, Cozy, Russian River Retreat in the Redwoods. Private Garden View Unit Guerneville 10/10 Exceptional (19) "We thoroughly enjoyed our three-day stay here. The place is conveniently located to Guerneville, the Russian River Beaches, and the coast. Located in the redwoods a short way up a road off the River Road, it is a quiet and relaxing getaway while minutes away from the fun and charms of the Russian River recreational and scenic areas. " CA $223 CA $415 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Guerneville-Hotels-Quiet.h99391569.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104530000/104524200/104524141/877bd48a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/105000000/104530000/104524200/104524141/c86d228a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/105000000/104530000/104524200/104524141/be8dec30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/105000000/104530000/104524200/104524141/be7c5c09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Honeymoon Suite w/ 2 Beds & Private Kitchen Saint Helena 10/10 Exceptional (21) "We had an outstanding time staying in St Helena am most importantly in this beautiful villa at the Inn of St Helena. Totally private and serene. This was a perfect place to stay to kick off my birthday trip. I hope we can come back. " CA $413 CA $806 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/St-Helena-Hotels-8-Room-Bed-And-Breakfast-Located-In-Downtown-St-Helena.h104524141.Hotel-Information) ![5 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/105000000/104500000/104495100/104495082/2b7ea862.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/105000000/104500000/104495100/104495082/98706733.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/105000000/104500000/104495100/104495082/bc4b96ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, books](https://images.trvl-media.com/lodging/105000000/104500000/104495100/104495082/f07eb1fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Bed & Breakfast Whole House Rental w Breakfast Included Saint Helena 9.8/10 Exceptional (26) "Welcoming and comfortable " CA $1,401 CA $2,406 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/St-Helena-Hotels-Historic-Bed-Breakfast-Whole-House-Rental-W-Breakfast-Included.h104495082.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/105000000/104520000/104519400/104519399/f36444a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/105000000/104520000/104519400/104519399/47f2f273.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/105000000/104520000/104519400/104519399/efbf02d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/105000000/104520000/104519400/104519399/caf78214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Delightful Downtown Cottage House with Modern Amenities (Breakfast Possible) St. Helena 9.6/10 Exceptional (23) "Great location! Property needs updating. Manager needs better customer service. " CA $919 CA $1,794 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/St-Helena-Hotels-Delightful-Downtown-Cottage-House-With-Modern-Amenities.h104519399.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=2025-10-25&endDate=2025-10-26®ionId=9542&adults=2&lodging=GUEST_HOUSE&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%2FWindsor-Guest-Houses.d9542-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindsor-Guest-Houses.d9542-aaGuestHouses.Travel-Guide-Accommodation) ## Top Windsor Hotel Reviews ![The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/920000/919800/919721/6551e7d3_y.jpg) ### The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel 10/10 Excellent "Staff was super helpful and very nice 😊 " [](https://expedia.ca/Santa-Rosa-Hotels-The-Sandman.h919721.Hotel-Information) ![The Inn at the Tides](//images.trvl-media.com/lodging/1000000/20000/11800/11786/cb3cd68d_y.jpg) ### The Inn at the Tides 10/10 Excellent "We were able to park right outside our door or very nearby. The cleaning staff was excellent. We also enjoyed a wide variety of breakfast choices, from a complimentary continental breakfast to other discounted breakfasts. Great place to stay!" [](https://expedia.ca/Bodega-Bay-Hotels-The-Inn-At-The-Tides.h11786.Hotel-Information) ![La Quinta Inn & Suites Santa Rosa Sonoma](//images.trvl-media.com/lodging/52000000/51320000/51310500/51310420/ea57e76d_y.jpg) ### La Quinta Inn & Suites Santa Rosa Sonoma 10/10 Excellent "Clean rooms, friendly staff" [](https://expedia.ca/Santa-Rosa-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Santa-Rosa.h51310420.Hotel-Information) ![Hotel La Rose](//images.trvl-media.com/lodging/8000000/7300000/7292500/7292445/65a52794_y.jpg) ### Hotel La Rose 10/10 Excellent "Beat " [](https://expedia.ca/Santa-Rosa-Hotels-Hotel-La-Rose.h7292445.Hotel-Information) ![Holiday Inn Express® Windsor Sonoma Wine Country by IHG](//images.trvl-media.com/lodging/2000000/1280000/1273400/1273394/6e9c3a9c_y.jpg) ### Holiday Inn Express® Windsor Sonoma Wine Country by IHG 10/10 Excellent "perfect for us while passing through" [](https://expedia.ca/Windsor-Hotels-Holiday-Inn-Express-Windsor-Sonoma-Wine-Country.h1273394.Hotel-Information) ![Home2 Suites by Hilton Petaluma](//images.trvl-media.com/lodging/85000000/84210000/84202500/84202457/1d9acb2a_y.jpg) ### Home2 Suites by Hilton Petaluma 10/10 Excellent "My stay was overall great. The staff and room was nice. I am super picky with cleanliness. There were a few hairs in the shower but other than that, it was super clean. Also, there was a problem with the room card system but the staff was great and tried to make an inconvenience very convenient. They were kind and patient and very welcoming." [](https://expedia.ca/Petaluma-Hotels-Home2-Suites-BY-Hilton-Petaluma.h84202457.Hotel-Information) ![Sonoma Winegrower's Inn](//images.trvl-media.com/lodging/1000000/10000/3900/3821/c006ddb7_y.jpg) ### Sonoma Winegrower's Inn 10/10 Excellent "The breakfast was good " [](https://expedia.ca/Rohnert-Park-Hotels-Best-Western-Sonoma-Winegrowers-Inn.h3821.Hotel-Information) ![Oxford Suites Sonoma County](//images.trvl-media.com/lodging/16000000/15930000/15927800/15927732/03c264d1_y.jpg) ### Oxford Suites Sonoma County 10/10 Excellent "Perfect location for Grayton casino. They offer free Shuttle rides to the casino also. rooms are nice and clean. Service is excellent. Recommended." [](https://expedia.ca/Rohnert-Park-Hotels-Oxford-Suites-Sonoma-County.h15927732.Hotel-Information) ![Hotel Centro Sonoma Wine Country, Tapestry Collection Hilton](//images.trvl-media.com/lodging/39000000/38320000/38318300/38318220/w3840h2634x0y0-aa114b9a_y.jpg) ### Hotel Centro Sonoma Wine Country, Tapestry Collection Hilton 10/10 Excellent "Clean room, nice bathroom, big fireplace in lobby, EV charger " [](https://expedia.ca/Rohnert-Park-Hotels-Hotel-Centro-Sonoma-Wine-Country.h38318220.Hotel-Information) ## Find out more about Windsor ## Windsor Guest Houses information | Number of reviews | 1,342 | | --- | --- | | Accommodation | 18 Guest Houses | | Lowest Price | CA $258 | | Highest Price | CA $2,406 | ## Explore a world of travel with Expedia - Lodging - Flights - Cars - More ways to book - [4 Star Hotels in Chalk Hill](https://www.expedia.ca/4Star-Chalk-Hill-Hotels.s40-0-d736342871657291776.Travel-Guide-Filter-Hotels) - [Apartments in Angel Island](https://www.expedia.ca/Angel-Island-Apartments.d502570-aaApartments.Travel-Guide-Accommodation) - 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[Aparthotels in Treasure Island](https://www.expedia.ca/Treasure-Island-Apart-Hotels.d506142-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Treasure Island](https://www.expedia.ca/Treasure-Island-Bed-And-Breakfast.d506142-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Treasure Island](https://www.expedia.ca/Treasure-Island-Cabins.d506142-aaCabins.Travel-Guide-Accommodation) - [Capsule Hotels in Treasure Island](https://www.expedia.ca/Treasure-Island-Capsule-Hotels.d506142-aaCapsuleHotels.Travel-Guide-Accommodation) - [Guest Houses in Treasure Island](https://www.expedia.ca/Treasure-Island-Guest-Houses.d506142-aaGuestHouses.Travel-Guide-Accommodation) - [Holiday Park Resorts in Treasure Island](https://www.expedia.ca/Treasure-Island-Holiday-Parks.d506142-aaHolidayParks.Travel-Guide-Accommodation) - [Hostels in Treasure Island](https://www.expedia.ca/Treasure-Island-Hostels.d506142-aaHostels.Travel-Guide-Accommodation) - [Inns in Treasure Island](https://www.expedia.ca/Treasure-Island-Inns.d506142-aaInns.Travel-Guide-Accommodation) - 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