Title: Middletown Guest Houses from CA $258 | Expedia.ca [Hotels in Middletown](https://expedia.ca/Middletown-Hotels.d180934.Travel-Guide-Hotels)[Vacation Rentals in Middletown](https://expedia.ca/Middletown-Vacation-Rentals.d180934.Travel-Guide-VacationRentals)[Middletown Car Rentals](https://expedia.ca/Car-Rentals-In-Middletown.d180934.Car-Rental-Guide)[Middletown Vacation Packages](https://expedia.ca/Middletown.d180934.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/7d3c785c1b89812c0f51c3c641644805.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Shannon Willitts # Search Guest Houses in Middletown 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=180934&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=180934&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=180934&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=180934&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Middletown Guest Houses ![Property grounds](https://images.trvl-media.com/lodging/8000000/7330000/7326600/7326527/0132d592.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) ![30-inch TV with cable channels, fireplace](https://images.trvl-media.com/lodging/8000000/7330000/7326600/7326527/d5a93698.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) ### 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) ![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) ![Reception](https://images.trvl-media.com/lodging/7000000/6950000/6948800/6948795/ca9bff2e.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) ![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) ![Dining](https://images.trvl-media.com/lodging/105000000/104530000/104524200/104524141/9d7175fb.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) ![Exterior](https://images.trvl-media.com/lodging/105000000/104520000/104519400/104519399/f36444a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/105000000/104520000/104519400/104519399/355f0d84.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) ![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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104500000/104495100/104495082/86b870fc.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) 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=180934&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%2FMiddletown-Guest-Houses.d180934-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMiddletown-Guest-Houses.d180934-aaGuestHouses.Travel-Guide-Accommodation) ## Top Middletown Hotel Reviews ![El Bonita Motel](//images.trvl-media.com/lodging/10000000/9450000/9444400/9444378/w650h427x0y0-bb96c582_y.jpg) ### El Bonita Motel 10/10 Excellent "Great clean affordable motel in Napa Valley! Would recommend to friends and family " [](https://expedia.ca/St-Helena-Hotels-El-Bonita-Motel.h9444378.Hotel-Information) ![Golden Haven Hot Springs](//images.trvl-media.com/lodging/10000000/9860000/9857000/9856954/cde0eb66_y.jpg) ### Golden Haven Hot Springs 10/10 Excellent "Accommodating, friendly, very relaxing. Can’t ask for anything more when staying at a spa!" [](https://expedia.ca/Calistoga-Hotels-Golden-Haven-Hot-Springs.h9856954.Hotel-Information) ![Harvest Inn](//images.trvl-media.com/lodging/1000000/530000/527100/527073/1943198c_y.jpg) ### Harvest Inn 10/10 Excellent "We thought the meals were fine but not outstanding. We loved the property. So beautiful!! " [](https://expedia.ca/St-Helena-Hotels-Harvest-Inn.h527073.Hotel-Information) ![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) ![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) ![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) ![Hotel E](//images.trvl-media.com/lodging/33000000/32790000/32786000/32785942/b9103eda_y.jpg) ### Hotel E 10/10 Excellent "Clean room, they let us check in early. Not much to do around town, everything closes late and closes early. Lots of homeless around property in the plaza do not recommend walking around " [](https://expedia.ca/Santa-Rosa-Hotels-Hotel-E.h32785942.Hotel-Information) ## Find out more about Middletown ## Middletown Guest Houses information | Number of reviews | 998 | | --- | --- | | Accommodation | 14 Guest Houses | | Lowest Price | CA $258 | | Highest Price | CA $2,406 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [5 Star Hotels in Calistoga](https://www.expedia.ca/5Star-Calistoga-Hotels.s50-0-d6668.Travel-Guide-Filter-Hotels) - [Aetna Springs Hotels](https://www.expedia.ca/Aetna-Springs-Hotels.d553248635975873533.Travel-Guide-Hotels) - [Resorts in Aetna Springs](https://www.expedia.ca/Aetna-Springs-Resort-Hotels.d553248635975873533-aaResortHotels.Travel-Guide-Accommodation) - [Apartments in Angel Island](https://www.expedia.ca/Angel-Island-Apartments.d502570-aaApartments.Travel-Guide-Accommodation) - [Condo Rentals in Angel Island](https://www.expedia.ca/Angel-Island-Condos.d502570-aaCondos.Travel-Guide-Accommodation) - 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