Title: Hillsboro Vacation Home Rentals from CA $578: Search Top Private Vacation Homes for Rent | Expedia.ca [Hotels in Hillsboro](https://expedia.ca/Hillsboro-Hotels.d553248634999258593.Travel-Guide-Hotels)[Vacation Rentals in Hillsboro](https://expedia.ca/Hillsboro-Vacation-Rentals.d553248634999258593.Travel-Guide-VacationRentals)[Hillsboro Car Rentals](https://expedia.ca/Car-Rentals-In-Hillsboro.d553248634999258593.Car-Rental-Guide)[Hillsboro Vacation Packages](https://expedia.ca/Hillsboro.d553248634999258593.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Hillsboro 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=553248634999258593&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248634999258593&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248634999258593&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248634999258593&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=VACATION_HOME&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Hillsboro Vacation Homes ![Property grounds](https://images.trvl-media.com/lodging/72000000/71760000/71756700/71756692/a1d87464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/72000000/71760000/71756700/71756692/cc67a3c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/72000000/71760000/71756700/71756692/f9a95f78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71760000/71756700/71756692/7fda792d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Turnbridge Manor Denton 9.8/10 Exceptional (12) "We rented this wonderful home for Christmas and had the most relaxing time. The house is just as advertised and the owner a delight to work with. We especially loved the proximity to the square and how walkable it was to everything. I can’t wait to rent it again during warm weather to enjoy all the wonderful porches and the outdoor area." CA $504 CA $854 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Denton-Hotels-Turnbridge-Manor.h71756692.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/ee0975c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/9eb7ac3d.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/103000000/102640000/102631200/102631144/259066d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/103000000/102640000/102631200/102631144/25541a3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### HGTV quality, private guest suite, country getaway with hot tub & fire pit Centreville 10/10 Exceptional (6) "Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!" CA $307 CA $661 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Centreville-Hotels-Private.h102631144.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/737f2153.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/23f1d475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/30ebd57e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/100000000/99840000/99830400/99830322/2a64ee56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious 2 bedroom duplex located conveniently near Route 50 East and West. Grasonville 9.6/10 Exceptional (12) "Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. " CA $350 CA $578 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Spacious-2-Bedroom-Duplex-Located-Conveniently-Near-Route-50-East-And-West.h99830322.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=553248634999258593&adults=2&lodging=VACATION_HOME&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%2FHillsboro-Private-Vacation-Homes.d553248634999258593-aaPrivateVacationHomes.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHillsboro-Private-Vacation-Homes.d553248634999258593-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Hillsboro Hotel Reviews ![Best Western Kent Narrows Inn](//images.trvl-media.com/lodging/1000000/20000/11300/11278/3968d160_y.jpg) ### Best Western Kent Narrows Inn 10/10 Excellent "Clean room and good location to biking trail." [](https://expedia.ca/Grasonville-Hotels-Best-Western-Kent-Narrows-Inn.h11278.Hotel-Information) ![Holiday Inn Express Annapolis East-Kent Island by IHG](//images.trvl-media.com/lodging/1000000/120000/117000/116919/a8fad934_y.jpg) ### Holiday Inn Express Annapolis East-Kent Island by IHG 10/10 Excellent "Very clean nice hotel next to the inland waterway , beautiful view on rear patio " [](https://expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![Cass-N-Reel Luxury Houseboat](//images.trvl-media.com/lodging/95000000/94680000/94672700/94672644/w1799h1199x1y1-608c1c0e_y.jpg) ### Cass-N-Reel Luxury Houseboat 10/10 Excellent "Place was lovely, great view, relaxing atmosphere, walk to local restaurants and marinas, fantastic!" [](https://expedia.ca/Grasonville-Hotels-Cass-N-Reel-Luxury-Houseboat.h94672644.Hotel-Information) ![The Wildset](//images.trvl-media.com/lodging/65000000/64420000/64410600/64410566/38a42051_y.jpg) ### The Wildset 10/10 Excellent "very clean - super friendly staff and wonderful vibe. Bed was super comfy as well! Only issue was someone’s takeout box with leftover food was left in the room fridge. " [](https://expedia.ca/St-Michaels-Hotels-The-Wildset.h64410566.Hotel-Information) ![St Michaels Inn](//images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg) ### St Michaels Inn 10/10 Excellent "Room was clean, Staff was very friendly and welcoming. " [](https://expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ![Best Western Plus Easton Inn & Suites](//images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/bedcc35b_y.jpg) ### Best Western Plus Easton Inn & Suites 10/10 Excellent "Excellent staff, very clean room, good hotel breakfast " [](https://expedia.ca/Easton-Hotels-Best-Western-Plus-Easton-Inn-Suites.h6846089.Hotel-Information) ![Best Western Denton Inn](//images.trvl-media.com/lodging/2000000/1110000/1101900/1101833/9475aafe_y.jpg) ### Best Western Denton Inn 10/10 Excellent "Friendly staff, excellent breakfast." [](https://expedia.ca/Denton-Hotels-Best-Western-Denton-Inn.h1101833.Hotel-Information) ![Hilton Garden Inn Kent Island Marina](//images.trvl-media.com/lodging/2000000/1230000/1222200/1222176/367a733a_y.jpg) ### Hilton Garden Inn Kent Island Marina 10/10 Excellent "This is also a relatively new hotel to area and has an excellent lounge and it okay dining options. The rooms were clean and wonderfully decorated. The location is superb. " [](https://expedia.ca/Grasonville-Hotels-Hilton-Garden-Inn-Kent-Island.h1222176.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/20000/11400/11364/fbc96e63_y.jpg) ### Quality Inn 10/10 Excellent "the room was spacious and relaxing. it was nice and very comfortable. I would stay here again" [](https://expedia.ca/Easton-Hotels-Quality-Inn.h11364.Hotel-Information) ## Find out more about Hillsboro ## Hillsboro Vacation Homes information | Number of reviews | 29 | | --- | --- | | Accommodation | 92 Vacation Homes | | Lowest Price | CA $578 | | Highest Price | CA $854 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Eastern Shore](https://www.expedia.ca/4Star-Eastern-Shore-Hotels.s40-0-d6025644.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Eastern Shore](https://www.expedia.ca/5Star-Eastern-Shore-Hotels.s50-0-d6025644.Travel-Guide-Filter-Hotels) - [Hotels near Avalon Theatre](https://www.expedia.ca/Avalon-Theatre-Hotels.0-l6286426-0.Travel-Guide-Filter-Hotels) - [Farmstay in Centreville](https://www.expedia.ca/Centreville-Agritourism.d88125-aaAgritourism.Travel-Guide-Accommodation) - [Chalets in Centreville](https://www.expedia.ca/Centreville-Chalets.d88125-aaChalets.Travel-Guide-Accommodation) - 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[Rental cars Easton - Newnam airport](https://www.expedia.ca/Car-Rentals-In-Easton-Newnam.d6027707.Car-Rental-Guide) - [Car rental Easton](https://www.expedia.ca/Car-Rentals-In-Easton.d7120.Car-Rental-Guide) - [Car rental Queenstown](https://www.expedia.ca/Car-Rentals-In-Queenstown.d56094.Car-Rental-Guide) - [Enterprise Rental Cars in Eastern Shore](https://www.expedia.ca/Enterprise-Car-Rentals-In-Eastern-Shore.d6025644-c15.Car-Rental-Guide-Suppliers) - [Rent A Wreck Rental Cars in Eastern Shore](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-Eastern-Shore.d6025644-c33.Car-Rental-Guide-Suppliers) - [Thrifty Car Rental Rental Cars in Eastern Shore](https://www.expedia.ca/Thrifty-Car-Rental-Car-Rentals-In-Eastern-Shore.d6025644-c45.Car-Rental-Guide-Suppliers) - [Centreville Vacation Rentals](https://www.expedia.ca/Centreville-Vacation-Rentals.d88125.Travel-Guide-VacationRentals) - [Eastern Shore Vacation Rentals](https://www.expedia.ca/Eastern-Shore-Vacation-Rentals.d6025644.Travel-Guide-VacationRentals) - [Easton Vacation Rentals](https://www.expedia.ca/Easton-Vacation-Rentals.d7120.Travel-Guide-VacationRentals) - [Book Vacation Homes in Hillsboro on Expedia.com](https://www.expedia.com/Hillsboro-Private-Vacation-Homes.d553248634999258593-aaPrivateVacationHomes.Travel-Guide-Accommodation)