Title: Middletown Condo Rentals from CA $782 | 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) ![Awesome place just to relax. ](https://images.trvl-media.com/place/180934/0cf53fed-8c67-4d1d-be6d-adcfe858199c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Matthew Walls # Search Condos Rentals in Middletown from CA $782 - ![](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 [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=180934&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=180934&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=180934&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 two months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=180934&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 Middletown Condo Rentals ![Exterior](https://images.trvl-media.com/lodging/35000000/34280000/34274800/34274712/61de8372.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/35000000/34280000/34274800/34274712/abbea1a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/35000000/34280000/34274800/34274712/c0ad68e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34280000/34274800/34274712/521f9417.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sip, Taste, Hot Tub, Repeat - Full Resort Access - Sleeps 6 Windsor 9.2/10 Wonderful (43) "Check-in was a little difficult, but the condo itself was convenient and a great stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) SB L. CA $314 CA $782 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Windsor-Hotels-Sip.h34274712.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=2025-12-17&endDate=2025-12-18®ionId=180934&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_180934) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+California%2C+United+States+of+America®ionId=180934&latLong=38.752403%2C-122.614983&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=CABIN) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+California%2C+United+States+of+America®ionId=180934&latLong=38.752403%2C-122.614983&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=COTTAGE) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+California%2C+United+States+of+America®ionId=180934&latLong=38.752403%2C-122.614983&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+California%2C+United+States+of+America®ionId=180934&latLong=38.752403%2C-122.614983&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=APARTMENT) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+California%2C+United+States+of+America®ionId=180934&latLong=38.752403%2C-122.614983&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=VACATION_HOME) Condos [](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+California%2C+United+States+of+America®ionId=180934&latLong=38.752403%2C-122.614983&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+California%2C+United+States+of+America®ionId=180934&latLong=38.752403%2C-122.614983&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&lodging=VILLA) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Middletown%2C+California%2C+United+States+of+America®ionId=180934&latLong=38.752403%2C-122.614983&adults=2&startDate=2026-03-03&d1=2026-03-03&endDate=2026-03-06&d2=2026-03-06&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%2FMiddletown-Condos.d180934-aaCondos.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FMiddletown-Condos.d180934-aaCondos.Travel-Guide-Accommodation) ## Top Middletown Hotel Reviews ![Appellation Healdsburg](https://images.trvl-media.com/lodging/119000000/118740000/118739000/118738917/4fc40d21_y.jpg) ### Appellation Healdsburg 10/10 Excellent "Love the facility, dinner menu, and their hospitality from checked in, food service and valet. " [](https://expedia.ca/Healdsburg-Hotels-Appellation-Healdsburg.h118738917.Hotel-Information) ![Calistoga Motor Lodge and Spa](https://images.trvl-media.com/lodging/1000000/100000/94200/94121/0c2722fb_y.jpg) ### Calistoga Motor Lodge and Spa 10/10 Excellent "Great room. Wonderful restaurants. Pools are clean and well maintained." [](https://expedia.ca/Calistoga-Hotels-Calistoga-Motor-Lodge-And-Spa.h94121.Hotel-Information) ![Harvest Inn](https://images.trvl-media.com/lodging/1000000/530000/527100/527073/1943198c_y.jpg) ### Harvest Inn 10/10 Excellent "Clean, great location and staff was great." [](https://expedia.ca/St-Helena-Hotels-Harvest-Inn.h527073.Hotel-Information) ![El Bonita Motel](https://images.trvl-media.com/lodging/10000000/9450000/9444400/9444378/f785b229_y.jpg) ### El Bonita Motel 10/10 Excellent "Ideal location, dog friendly, big rooms, great value!" [](https://expedia.ca/St-Helena-Hotels-El-Bonita-Motel.h9444378.Hotel-Information) ![Hotel La Rose](https://images.trvl-media.com/lodging/8000000/7300000/7292500/7292445/65a52794_y.jpg) ### Hotel La Rose 10/10 Excellent "Hotel La Rose is such a sweet and charming place to stay. I felt like I stepped into a hallmark Christmas movie! Loved it. Quiet, nice location, and very cool room. " [](https://expedia.ca/Santa-Rosa-Hotels-Hotel-La-Rose.h7292445.Hotel-Information) ![Holiday Inn Windsor Wine Country by IHG](https://images.trvl-media.com/lodging/14000000/13240000/13235900/13235845/48ef5836_y.jpg) ### Holiday Inn Windsor Wine Country by IHG 10/10 Excellent "Everything was perfect.. the room was clean the bathroom was excellent. Except the door squeaked which was kind of scary. Lol but overall the hotel was perfect" [](https://expedia.ca/Windsor-Hotels-Holiday-Inn-Windsor-Wine-Country.h13235845.Hotel-Information) ![The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/920000/919800/919721/6551e7d3_y.jpg) ### The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel 10/10 Excellent "We will be back , it is a perfect location when heading to SF , it was a nice room and nice amenties, close to pool, breakfast and fire pit" [](https://expedia.ca/Santa-Rosa-Hotels-The-Sandman.h919721.Hotel-Information) ![Art House Hotel and Suites](https://images.trvl-media.com/lodging/67000000/66160000/66153800/66153742/4c9b91b9_y.jpg) ### Art House Hotel and Suites 10/10 Excellent "Rooms are clean and modern. The staff is very friendly. " [](https://expedia.ca/Santa-Rosa-Hotels-Art-House-Hotel.h66153742.Hotel-Information) ![Hotel E](https://images.trvl-media.com/lodging/33000000/32790000/32786000/32785942/b9103eda_y.jpg) ### Hotel E 10/10 Excellent "Hotel room was very clean. Nice spacious bathroom, with good water pressure. Staff was informative and friendly. Will definitely come back again. " [](https://expedia.ca/Santa-Rosa-Hotels-Hotel-E.h32785942.Hotel-Information) ## Find out more about Middletown ## Middletown Condo Rentals information | Number of reviews | 44 | | --- | --- | | Accommodation | 23 Condo Rentals | | Lowest Price | CA $782 | | Highest Price | CA $782 | ## Frequently asked questions ### Why book your condo in Middletown with Expedia? > Vacationing shouldn't be difficult, so if you're in search of condos at a great price, Expedia has your back. Save cash and select something cheap and cheerful, or splurge on a 5-star condo and really spoil your crew. Use our convenient search filters to find a stay in Middletown that suits your style. ### How can I find cheap condos in Middletown? > The best way to locate cheap condos in Middletown is with Expedia's easy-to-use filter tool. Refine your search results by budget, amenities and star rating to nab unbeatable rates with only a few clicks. ### What is there to do in Middletown near my condo? > After you've unpacked your bags, set out and explore the fantastic things Middletown has to offer. 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