Title: Winchester Villas from CA $111 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d553248635975872164.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d553248635975872164.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d553248635975872164.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d553248635975872164.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Winchester Villa Rentals from CA $111 ![](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 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635975872164&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635975872164&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635975872164&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635975872164&startDate=2026-02-06&endDate=2026-02-08&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester Villas We don't have any properties that match your exact search [See all properties in Winchester](https://expedia.ca/Hotel-Search?startDate=2025-10-29&endDate=2025-10-30®ionId=553248635975872164&adults=2) ## Recommended hotels in Winchester ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/11300/11260/8c4bdae3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11300/11260/01da12a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lockers](https://images.trvl-media.com/lodging/1000000/20000/11300/11260/0383cc4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 2 Double Beds, Non Smoking, Kitchenette](https://images.trvl-media.com/lodging/1000000/20000/11300/11260/bca43f6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn Perryville Perryville 9.2/10 Wonderful (73) "Amazing location, staff and cleanliness is top notch. " CA $100 CA $112 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Perryville-Hotels-Red-Roof-Inn-Perryville.h11260.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/53ee3fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, free WiFi, bed sheets](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/fe97576e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/a0c80d79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/82000000/81270000/81261300/81261283/879c8a94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Middletown Middletown 9.2/10 Wonderful (293) "One of the best hotels I have ever stayed " CA $147 CA $164 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Middletown-Hotels-Fairfield-Inn-Suites-By-Marriott-Middletown.h81261283.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/1feae509.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/3cc8ea80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/dc410dcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34800000/34796100/34796045/0669e46a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Middletown by IHG Middletown 9.2/10 Wonderful (628) "This was a great relaxing stay" CA $145 CA $161 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Wilmington-Hotels-Holiday-Inn-Express-And-Suites-Middletown.h34796045.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1290000/1283800/1283746/68f18dfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1290000/1283800/1283746/444bee4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1290000/1283800/1283746/051e307b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 2 Double Beds, Non Smoking (Oversized)](https://images.trvl-media.com/lodging/2000000/1290000/1283800/1283746/eceeb6c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Newark - Elkton Elkton 9.0/10 Wonderful (1005) "Good coffee and nice room" CA $124 CA $139 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Elkton-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Newark-Elkton.h1283746.Hotel-Information) ![Interior entrance](https://images.trvl-media.com/lodging/103000000/102740000/102739400/102739320/a4e2953f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, designer toiletries, hair dryer, slippers](https://images.trvl-media.com/lodging/103000000/102740000/102739400/102739320/19ccd7c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch Smart TV with digital channels](https://images.trvl-media.com/lodging/103000000/102740000/102739400/102739320/2b79390d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch Smart TV with digital channels](https://images.trvl-media.com/lodging/103000000/102740000/102739400/102739320/0e0598f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Artelo Kennett Square 9.8/10 Exceptional (61) "Beautiful room, wonderful area!" CA $177 CA $197 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Kennett-Square-Hotels-Artelo.h102739320.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/9000000/8510000/8507200/8507156/4b20ab4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/9000000/8510000/8507200/8507156/bed177a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/9000000/8510000/8507200/8507156/e7f5d4e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Soundproofing, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/9000000/8510000/8507200/8507156/8a6d85fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites Wilmington New Castle New Castle 8.8/10 Excellent (894) "Great hotel close to a lot of amenities " CA $147 CA $163 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Wilmington-Hotels-Fairfield-Inn-Suites-Wilmington-New-Castle.h8507156.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12000/11904/ea219a4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/12000/11904/6f7fa604.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/12000/11904/90c843ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/12000/11904/e4d0d0d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Newark - Wilmington Newark 9.0/10 Wonderful (1018) "Staff was very helpful during the check in process." CA $135 CA $150 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Wilmington-Hotels-Comfort-Inn-Suites-Newark-Wilmington.h11904.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/42000/41973/8470a785.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/1000000/50000/42000/41973/da8840fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/50000/42000/41973/b4ea9c0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/50000/42000/41973/b371460e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baymont by Wyndham Newark at University of Delaware Newark 7.8/10 Good (1013) "Very pleasant place to stay" CA $104 CA $115 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Wilmington-Hotels-Baymont-By-Wyndham-Newark-At-University-Of-Delaware.h41973.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/117000000/116860000/116852300/116852262/w1214h810x0y0-62841e7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/117000000/116860000/116852300/116852262/12e386c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/117000000/116860000/116852300/116852262/0e7e3fe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/117000000/116860000/116852300/116852262/957d7713.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn by Marriott Newark, DE Newark 9.8/10 Exceptional (6) CA $178 CA $198 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Newark-Hotels-Residence-Inn-By-Marriott-Newark.h116852262.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/9400/9312/f1191985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9400/9312/00ed810e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/9400/9312/629fbb29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/9400/9312/cb46b611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ramada by Wyndham Newark/Wilmington Newark 7.0/10 Good (1012) "Ashley & staff were excellent here i'd highly recommend for people to book here " CA $100 CA $111 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Wilmington-Hotels-Ramada-By-Wyndham-NewarkWilmington.h9312.Hotel-Information) ![Free self parking](https://images.trvl-media.com/lodging/116000000/115150000/115145600/115145541/b4a95140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/116000000/115150000/115145600/115145541/cf6aa34e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Studio, Garden View](https://images.trvl-media.com/lodging/116000000/115150000/115145600/115145541/bc80087c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/116000000/115150000/115145600/115145541/0f03c620.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Elkton Lodge - Newark - Elkton - University Gateway Elkton 8.4/10 Very good (15) "Affordable clean place to stay. " CA $138 CA $155 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/Elkton-Hotels-Elkton-Lodge.h115145541.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/990000/984900/984873/96caeac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/990000/984900/984873/628c8639.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/990000/984900/984873/75af64ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/1000000/990000/984900/984873/cb5cfe40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express North East by IHG North East 8.4/10 Very good (521) "I like the great hospitality and it was very clean good breakfast also" CA $156 CA $175 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/North-East-Hotels-Holiday-Inn-Express-North-East.h984873.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/98000000/97870000/97861600/97861549/22ee9748.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/98000000/97870000/97861600/97861549/93754896.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/98000000/97870000/97861600/97861549/a9d0f8e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/98000000/97870000/97861600/97861549/8d778bf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard By Marriott New Castle New Castle 8.6/10 Excellent (226) "Great place" CA $160 CA $178 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Courtyard-By-Marriott-New-Castle.h97861549.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119450000/119444000/119443969/b2d822f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi](https://images.trvl-media.com/lodging/120000000/119450000/119444000/119443969/6a8f522f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/120000000/119450000/119444000/119443969/d4c4f3bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi](https://images.trvl-media.com/lodging/120000000/119450000/119444000/119443969/09c9b155.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Woodspring Suites Wilmington Riverfront Wilmington CA $126 CA $139 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Wilmington-Hotels-Woodspring-Suites-Wilmington-Riverfront.h119443969.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892600/892594/936a8c33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One bedroom suite one king non smoking](https://images.trvl-media.com/lodging/1000000/900000/892600/892594/ebc9c9e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892600/892594/9665cb6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily self-serve breakfast](https://images.trvl-media.com/lodging/1000000/900000/892600/892594/05ce901b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Elkton Elkton 8.6/10 Excellent (728) "Great staff!" CA $126 CA $141 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Elkton-Hotels-Hampton-Inn-Elkton.h892594.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/900500/900419/6179b7b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Refrigerator & Microwave (with Sofabed)](https://images.trvl-media.com/lodging/1000000/910000/900500/900419/10fce65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/910000/900500/900419/1f832bfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/910000/900500/900419/a4f6753f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Newark/Christiana Inn Bear 7.2/10 Good (1015) "A good stay " CA $124 CA $138 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Wilmington-Hotels-Best-Western-Plus-NewarkChristiana-Inn.h900419.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/870000/861400/861316/7a1b8834.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/870000/861400/861316/bf528c84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/1000000/870000/861400/861316/04e8b2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/870000/861400/861316/04ab1eb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Mendenhall Chadds Ford 9.0/10 Wonderful (1009) "Staff are very friendly." CA $195 CA $217 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Exton-Hotels-Inn-At-Mendenhall.h861316.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/6a6a4995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/6cc4a825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/50463ffe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, blackout drapes, iron/ironing board, cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1490000/1485700/1485615/c38ba9d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Middletown Middletown 8.8/10 Excellent (841) "Enjoyed the amenities and great location for shops nearby " CA $149 CA $165 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Wilmington-Hotels-Hampton-Inn-Middletown.h1485615.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2810000/2804200/2804110/b3bb2c7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2810000/2804200/2804110/bb33cd98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2810000/2804200/2804110/71317bb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/2810000/2804200/2804110/99b0adb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn by Marriott Kennett Square Brandywine Valley Kennett Square 8.8/10 Excellent (1009) "One of the best places to stay with convenience to longwood gardens and many restaurants ." CA $178 CA $198 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Exton-Hotels-Fairfield-Inn-By-Marriott-Kennett-Square-Brandywine-Valley.h2804110.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/16000000/15090000/15082800/15082750/244a9df9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/16000000/15090000/15082800/15082750/c03fee2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Chesapeake Haven)](https://images.trvl-media.com/lodging/16000000/15090000/15082800/15082750/90041687.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/16000000/15090000/15082800/15082750/a3733b24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn At The Canal Bed & Breakfast Chesapeake City 8.6/10 Excellent (504) "The property owner, Ed, was fabulous. I cannot say enough wonderful things about his hospitality and the Inn is in a perfect location." CA $232 CA $246 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Chesapeake-City-Hotels-Inn-At-The-Canal-Bed-Breakfast.h15082750.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=2025-10-29&endDate=2025-10-30®ionId=553248635975872164&adults=2&lodging=VILLA&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%2FWinchester-Villas.d553248635975872164-aaVillas.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Villas.d553248635975872164-aaVillas.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Embassy Suites by Hilton Newark Wilmington South](//images.trvl-media.com/lodging/1000000/330000/327600/327586/b7951f6a_y.jpg) ### Embassy Suites by Hilton Newark Wilmington South 10/10 Excellent "Much nicer than I expected. It was parents weekend, so cost more than it should. " [](https://expedia.ca/Wilmington-Hotels-Embassy-Suites-Newark-WilmingtonSouth.h327586.Hotel-Information) ![Staybridge Suites Wilmington Downtown by IHG](//images.trvl-media.com/lodging/82000000/81880000/81875700/81875625/d8ff2a29_y.jpg) ### Staybridge Suites Wilmington Downtown by IHG 10/10 Excellent "Great property, new and clean, friendly staff" [](https://expedia.ca/Wilmington-Hotels-Staybridge-Suites-Wilmington-Downtown.h81875625.Hotel-Information) ![Sheraton Suites Wilmington Downtown](//images.trvl-media.com/lodging/1000000/10000/4700/4693/72ec9ef5_y.jpg) ### Sheraton Suites Wilmington Downtown 10/10 Excellent "Clean room, great service. Parking slots in the garage are extremely narrow for today’s cars." [](https://expedia.ca/Wilmington-Hotels-Sheraton-Suites-Wilmington-Downtown.h4693.Hotel-Information) ![Sonesta Select Newark Christiana Mall](//images.trvl-media.com/lodging/1000000/10000/2100/2091/5b01ae08_y.jpg) ### Sonesta Select Newark Christiana Mall 10/10 Excellent "It was perfect for a night of a ling day driving. Convenient and quite." [](https://expedia.ca/Wilmington-Hotels-Sonesta-Select-Newark.h2091.Hotel-Information) ![Quality Inn Newark - Wilmington](//images.trvl-media.com/lodging/1000000/30000/25100/25008/e605848f_y.jpg) ### Quality Inn Newark - Wilmington 10/10 Excellent "Staff are kind and are respectful and polite ." [](https://expedia.ca/Wilmington-Hotels-Quality-Inn.h25008.Hotel-Information) ![Fairfield Inn by Marriott Kennett Square Brandywine Valley](//images.trvl-media.com/lodging/3000000/2810000/2804200/2804110/06c01027_y.jpg) ### Fairfield Inn by Marriott Kennett Square Brandywine Valley 10/10 Excellent "We were in town for a wedding and our stay was a pleasure. Our room was well apportioned and the bed was very comfortable. We appreciated the healthy and delicious breakfast choices." [](https://expedia.ca/Exton-Hotels-Fairfield-Inn-By-Marriott-Kennett-Square-Brandywine-Valley.h2804110.Hotel-Information) ![Best Western Plus Newark/Christiana Inn](//images.trvl-media.com/lodging/1000000/910000/900500/900419/bb536b3a_y.jpg) ### Best Western Plus Newark/Christiana Inn 10/10 Excellent "Raymond at the front desk was so friendly and accommodating. He explained everything and made recommendations for food. He seriously deserves a raise!! " [](https://expedia.ca/Wilmington-Hotels-Best-Western-Plus-NewarkChristiana-Inn.h900419.Hotel-Information) ![Sonesta ES Suites Wilmington - Newark](//images.trvl-media.com/lodging/1000000/20000/19100/19062/98de1f1c_y.jpg) ### Sonesta ES Suites Wilmington - Newark 10/10 Excellent "Good" [](https://expedia.ca/Wilmington-Hotels-Sonesta-ES-Suites-Wilmington-Newark.h19062.Hotel-Information) ![Baymont by Wyndham Newark at University of Delaware](//images.trvl-media.com/lodging/1000000/50000/42000/41973/b371460e_y.jpg) ### Baymont by Wyndham Newark at University of Delaware 10/10 Excellent "Well woorth the price. THE most important thing in a hotel room: shower....water pressure was awesome!🙂" [](https://expedia.ca/Wilmington-Hotels-Baymont-By-Wyndham-Newark-At-University-Of-Delaware.h41973.Hotel-Information) ## Find out more about Winchester ## Winchester Villas information | Number of reviews | 11,414 | | --- | --- | | Accommodation | 1 Villas | | Lowest Price | CA $111 | | Highest Price | CA $246 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Chesapeake City](https://www.expedia.ca/4Star-Chesapeake-City-Hotels.s40-0-d177517.Travel-Guide-Filter-Hotels) - [Apartments in Arundel](https://www.expedia.ca/Arundel-Apartments.d553248635975849826-aaApartments.Travel-Guide-Accommodation) - [Hotels near Bulle Rock Golf Course](https://www.expedia.ca/Bulle-Rock-Golf-Course-Hotels.0-l6091695-0.Travel-Guide-Filter-Hotels) - [B&B in Charlestown](https://www.expedia.ca/Charlestown-Bed-And-Breakfast.d553248634999088358-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Charlestown](https://www.expedia.ca/Charlestown-Guest-Houses.d553248634999088358-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in Charlestown](https://www.expedia.ca/Charlestown-Hotels-Cheap-Hotels.0-0-d553248634999088358-tCheapHotels.Travel-Guide-Filter-Hotels) - [Charlestown Hotels](https://www.expedia.ca/Charlestown-Hotels.d553248634999088358.Travel-Guide-Hotels) - [B&B in Chesapeake City](https://www.expedia.ca/Chesapeake-City-Bed-And-Breakfast.d177517-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cheap Hotels in Chesapeake City](https://www.expedia.ca/Chesapeake-City-Hotels-Cheap-Hotels.0-0-d177517-tCheapHotels.Travel-Guide-Filter-Hotels) - [Golf Hotels in Chesapeake City](https://www.expedia.ca/Chesapeake-City-Hotels-Golf-Hotel.0-0-d177517-tGolfHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Chesapeake City](https://www.expedia.ca/Chesapeake-City-Hotels-Luxury-Hotel.0-0-d177517-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Marriott Hotels & Resorts in Chesapeake City](https://www.expedia.ca/Chesapeake-City-Hotels-Marriott-Hotels-Resorts.0-0-d177517--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - [Spa Hotels in Chesapeake City](https://www.expedia.ca/Chesapeake-City-Hotels-Spa-Hotel.0-0-d177517-tSpaHotel.Travel-Guide-Filter-Hotels) - [Chesapeake City Hotels](https://www.expedia.ca/Chesapeake-City-Hotels.d177517.Travel-Guide-Hotels) - [Inns in Chesapeake City](https://www.expedia.ca/Chesapeake-City-Inns.d177517-aaInns.Travel-Guide-Accommodation) - [Farmstay in Childs](https://www.expedia.ca/Childs-Agritourism.d3000347838-aaAgritourism.Travel-Guide-Accommodation) - [Hotels with a Pool in Childs](https://www.expedia.ca/Childs-Hotels-Hotel-With-Pool.0-0-d3000347838-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Childs](https://www.expedia.ca/Childs-Hotels-Luxury-Hotel.0-0-d3000347838-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Childs Hotels](https://www.expedia.ca/Childs-Hotels.d3000347838.Travel-Guide-Hotels) - [Motels in Childs](https://www.expedia.ca/Childs-Motels.d3000347838-aaMotels.Travel-Guide-Accommodation) - [Resorts in Childs](https://www.expedia.ca/Childs-Resort-Hotels.d3000347838-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near Conowingo Dam](https://www.expedia.ca/Conowingo-Dam-Hotels.0-l553248621532662920-0.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Conowingo](https://www.expedia.ca/Conowingo-Hotels-Cheap-Hotels.0-0-d3000748811-tCheapHotels.Travel-Guide-Filter-Hotels) - [Conowingo Hotels](https://www.expedia.ca/Conowingo-Hotels.d3000748811.Travel-Guide-Hotels) - [Cecil County Hotels](https://www.expedia.ca/Destinations-In-Cecil-County.d553248635976434204.Hotel-Destinations) - [Earleville Hotels](https://www.expedia.ca/Earleville-Hotels.d6359189.Travel-Guide-Hotels) - [Apartments in Elk Mills](https://www.expedia.ca/Elk-Mills-Apartments.d3000347868-aaApartments.Travel-Guide-Accommodation) - [B&B in Elk Mills](https://www.expedia.ca/Elk-Mills-Bed-And-Breakfast.d3000347868-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Elk Mills Hotels](https://www.expedia.ca/Elk-Mills-Hotels.d3000347868.Travel-Guide-Hotels) - [Hotels near Elk Neck State Park](https://www.expedia.ca/Elk-Neck-State-Park-Hotels.0-l553248621532662916-0.Travel-Guide-Filter-Hotels) - [Cabin Rentals in Elkton](https://www.expedia.ca/Elkton-Cabins.d7834-aaCabins.Travel-Guide-Accommodation) - [Business Hotels in Elkton](https://www.expedia.ca/Elkton-Hotels-Business-Hotel.0-0-d7834-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Elkton](https://www.expedia.ca/Elkton-Hotels-Cheap-Hotels.0-0-d7834-tCheapHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Elkton](https://www.expedia.ca/Elkton-Hotels-Pet-Friendly-Hotel.0-0-d7834-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Elkton](https://www.expedia.ca/Elkton-Hotels-Spa-Hotel.0-0-d7834-tSpaHotel.Travel-Guide-Filter-Hotels) - [Elkton Hotels](https://www.expedia.ca/Elkton-Hotels.d7834.Travel-Guide-Hotels) - [Motels in Elkton](https://www.expedia.ca/Elkton-Motels.d7834-aaMotels.Travel-Guide-Accommodation) - [Hotels near Fair Hill State Natural Resources Management Area](https://www.expedia.ca/Fair-Hill-State-Natural-Resources-Management-Area-Hotels.0-l6187511-0.Travel-Guide-Filter-Hotels) - [B&B in Havre De Grace](https://www.expedia.ca/Havre-De-Grace-Bed-And-Breakfast.d55750-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cheap Hotels in Havre De Grace](https://www.expedia.ca/Havre-De-Grace-Hotels-Cheap-Hotels.0-0-d55750-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in Havre De Grace](https://www.expedia.ca/Havre-De-Grace-Hotels-Hotels-With-Smoking-Rooms.0-0-d55750-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Lgbt Friendly Hotels in Havre De Grace](https://www.expedia.ca/Havre-De-Grace-Hotels-LGBT-Friendly-Hotel.0-0-d55750-tLGBTFriendlyHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Havre De Grace](https://www.expedia.ca/Havre-De-Grace-Hotels-Luxury-Hotel.0-0-d55750-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Havre De Grace Hotels](https://www.expedia.ca/Havre-De-Grace-Hotels.d55750.Travel-Guide-Hotels) - [Motels in Havre De Grace](https://www.expedia.ca/Havre-De-Grace-Motels.d55750-aaMotels.Travel-Guide-Accommodation) - [Hotels near Havre de Grace Promenade](https://www.expedia.ca/Havre-De-Grace-Promenade-Hotels.0-l553248621532662835-0.Travel-Guide-Filter-Hotels) - [Townhomes in Havre De Grace](https://www.expedia.ca/Havre-De-Grace-Townhomes.d55750-aaTownhomes.Travel-Guide-Accommodation) - [Hotels near Historical Society of Cecil County](https://www.expedia.ca/Historical-Society-Of-Cecil-County-Hotels.0-l553248621561879715-0.Travel-Guide-Filter-Hotels) - [B&B in North East](https://www.expedia.ca/North-East-Bed-And-Breakfast.d139151-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Honeymoon Resorts and in North East](https://www.expedia.ca/North-East-Hotels-Honeymoon-Hotels.0-0-d139151-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in North East](https://www.expedia.ca/North-East-Hotels-Hotels-With-Hot-Tubs.0-0-d139151-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Luxury Hotels in North East](https://www.expedia.ca/North-East-Hotels-Luxury-Hotel.0-0-d139151-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in North East](https://www.expedia.ca/North-East-Hotels-Pet-Friendly-Hotel.0-0-d139151-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in North East](https://www.expedia.ca/North-East-Hotels-Spa-Hotel.0-0-d139151-tSpaHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in North East](https://www.expedia.ca/North-East-Hotels-Waterpark-Hotels.0-0-d139151-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in North East](https://www.expedia.ca/North-East-Hotels-Wedding-Hotels.0-0-d139151-tWeddingHotels.Travel-Guide-Filter-Hotels) - [North East Hotels](https://www.expedia.ca/North-East-Hotels.d139151.Travel-Guide-Hotels) - [Motels in North East](https://www.expedia.ca/North-East-Motels.d139151-aaMotels.Travel-Guide-Accommodation) - [Resorts in North East](https://www.expedia.ca/North-East-Resort-Hotels.d139151-aaResortHotels.Travel-Guide-Accommodation) - [Villas in Perry Point](https://www.expedia.ca/Perry-Point-Villas.d553248635975852837-aaVillas.Travel-Guide-Accommodation) - [La Quinta Inn & Suites Hotels in Perryville](https://www.expedia.ca/Perryville-Hotels-La-Quinta-Inn-Suites.0-0-d8217--bLaQuintaInnSuites.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Perryville](https://www.expedia.ca/Perryville-Hotels-Pet-Friendly-Hotel.0-0-d8217-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Perryville](https://www.expedia.ca/Perryville-Hotels-Spa-Hotel.0-0-d8217-tSpaHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Perryville](https://www.expedia.ca/Perryville-Hotels-Waterpark-Hotels.0-0-d8217-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Perryville Hotels](https://www.expedia.ca/Perryville-Hotels.d8217.Travel-Guide-Hotels) - [Port Deposit Hotels](https://www.expedia.ca/Port-Deposit-Hotels.d553248634999380172.Travel-Guide-Hotels) - [Red Point Hotels](https://www.expedia.ca/Red-Point-Hotels.d553248635975869447.Travel-Guide-Hotels) - [B&B in Rising Sun](https://www.expedia.ca/Rising-Sun-Bed-And-Breakfast.d6153612-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Casino Hotels in Rising Sun](https://www.expedia.ca/Rising-Sun-Hotels-Casino-Hotel.0-0-d6153612-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Rising Sun Hotels](https://www.expedia.ca/Rising-Sun-Hotels.d6153612.Travel-Guide-Hotels) - [Resorts in Rising Sun](https://www.expedia.ca/Rising-Sun-Resort-Hotels.d6153612-aaResortHotels.Travel-Guide-Accommodation) - [Villas in Rising Sun](https://www.expedia.ca/Rising-Sun-Villas.d6153612-aaVillas.Travel-Guide-Accommodation) - [Hotels near Susquehanna State Park](https://www.expedia.ca/Susquehanna-State-Park-Hotels.0-l553248621558141377-0.Travel-Guide-Filter-Hotels) - [B&B in Warwick](https://www.expedia.ca/Warwick-Bed-And-Breakfast.d553248635975870671-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Warwick](https://www.expedia.ca/Warwick-Guest-Houses.d553248635975870671-aaGuestHouses.Travel-Guide-Accommodation) - [Resorts in Warwick](https://www.expedia.ca/Warwick-Resort-Hotels.d553248635975870671-aaResortHotels.Travel-Guide-Accommodation) - [Aparthotels in White Crystal Beach](https://www.expedia.ca/White-Crystal-Beach-Apart-Hotels.d553248635975865930-aaApartHotels.Travel-Guide-Accommodation) - [B&B in White Crystal Beach](https://www.expedia.ca/White-Crystal-Beach-Bed-And-Breakfast.d553248635975865930-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cottages in White Crystal Beach](https://www.expedia.ca/White-Crystal-Beach-Cottages.d553248635975865930-aaCottages.Travel-Guide-Accommodation) - [White Crystal Beach Hotels](https://www.expedia.ca/White-Crystal-Beach-Hotels.d553248635975865930.Travel-Guide-Hotels) - [Motels in White Crystal Beach](https://www.expedia.ca/White-Crystal-Beach-Motels.d553248635975865930-aaMotels.Travel-Guide-Accommodation) - [Resorts in White Crystal Beach](https://www.expedia.ca/White-Crystal-Beach-Resort-Hotels.d553248635975865930-aaResortHotels.Travel-Guide-Accommodation) - [Flights to Elkton](https://www.expedia.ca/Cheap-Flights-To-Elkton.d7834.Travel-Guide-Flights) - [Flights to North East](https://www.expedia.ca/Cheap-Flights-To-North-East.d139151.Travel-Guide-Flights) - [Flights to Perryville](https://www.expedia.ca/Cheap-Flights-To-Perryville.d8217.Travel-Guide-Flights) - [Flights from North East](https://www.expedia.ca/lp/flights/139151/flights-from-north-east) - [Flights from Port Deposit](https://www.expedia.ca/lp/flights/553248634999380172/flights-from-port-deposit) - [Flights from Rising Sun](https://www.expedia.ca/lp/flights/6153612/flights-from-rising-sun) - [Flights from Elkton](https://www.expedia.ca/lp/flights/7834/flights-from-elkton) - [Bulle Rock Golf Course](https://www.expedia.ca/Bulle-Rock-Golf-Course-Havre-De-Grace.d6091695.Vacation-Attraction) - [Visit Chesapeake City](https://www.expedia.ca/Chesapeake-City.dx177517) - [Visit Elkton](https://www.expedia.ca/Elkton.dx7834) - [Harford Memorial Hospital](https://www.expedia.ca/Harford-Memorial-Hospital-Havre-De-Grace.d6289021.Vacation-Attraction) - [Visit Havre De Grace](https://www.expedia.ca/Havre-De-Grace.dx55750) - [North East Vacations](https://www.expedia.ca/North-East.d139151.Destination-Travel-Guides) - [Budget Rental Cars in Elkton](https://www.expedia.ca/Budget-Car-Rentals-In-Elkton.d7834-c39.Car-Rental-Guide-Suppliers) - [Car rentals in Budget Santa Maria Public Airport - 3249 Terminal Dr](https://www.expedia.ca/Budget-at-Santa-Maria-Public-Airport-3249-Terminal-Dr-Santa-Maria-California-USA.v7834.Car-Rental-Guide-Location) - [Car rental Elkton](https://www.expedia.ca/Car-Rentals-In-Elkton.d7834.Car-Rental-Guide) - [Car rental Havre De Grace](https://www.expedia.ca/Car-Rentals-In-Havre-De-Grace.d55750.Car-Rental-Guide) - [North East Vacation Rentals](https://www.expedia.ca/North-East-Vacation-Rentals.d139151.Travel-Guide-VacationRentals) - [Book Villas in Winchester on Expedia.com](https://www.expedia.com/Winchester-Villas.d553248635975872164-aaVillas.Travel-Guide-Accommodation)