Title: Book the Best HISTORIC Hotels in Winchester in 2026 | Expedia.ca [Winchester Travel Guide](https://expedia.ca/Winchester.dx5477)[Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d5477.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d5477.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d5477.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.ca/Things-To-Do-In-Winchester.d5477.Travel-Guide-Activities)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d5477.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d5477.Destination-Travel-Guides) ![Winchester which includes heritage architecture as well as a small group of people](https://images.trvl-media.com/place/5477/36ffd968-a708-44fd-a530-107c0f9501f1.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Winchester from CA $128 - ![](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 availability on Winchester Historic Hotels Tonight [Dec 14 - Dec 15](https://www.expedia.ca/Hotel-Search?regionId=5477&startDate=2025-12-14&endDate=2025-12-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 15 - Dec 16](https://www.expedia.ca/Hotel-Search?regionId=5477&startDate=2025-12-15&endDate=2025-12-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=5477&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=5477&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester historic hotels ![Terrace/patio](https://images.trvl-media.com/lodging/8000000/7730000/7728500/7728491/04abd54d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Suite](https://images.trvl-media.com/lodging/8000000/7730000/7728500/7728491/73acb33f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/8000000/7730000/7728500/7728491/6d21eba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/8000000/7730000/7728500/7728491/71414dd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel du Vin & Bistro Winchester [](https://www.expedia.ca/Winchester-Hotels-Hotel-Du-Vin-Bistro-Winchester.h7728491.Hotel-Information) Winchester 9.0/10 Wonderful (549) "The room was very clean, comfortable and it had everything I needed for my stay. " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Cliff CA $169 CA $203 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Winchester-Hotels-Hotel-Du-Vin-Bistro-Winchester.h7728491.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/23000000/22260000/22257700/22257620/dbf02c07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, 1 Double Bed, Ensuite, City View | View from room](https://images.trvl-media.com/lodging/23000000/22260000/22257700/22257620/6b5e1a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/23000000/22260000/22257700/22257620/b2424b86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, 1 Double Bed, Ensuite, City View](https://images.trvl-media.com/lodging/23000000/22260000/22257700/22257620/91f876b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Old Vine [](https://www.expedia.ca/Winchester-Hotels-The-Old-Vine.h22257620.Hotel-Information) Winchester 9.6/10 Exceptional (215) "Excellent restaurant. Very helpful staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Helen CA $231 CA $278 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Winchester-Hotels-The-Old-Vine.h22257620.Hotel-Information) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/20000/18600/18535/3b748348.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; British cuisine ](https://images.trvl-media.com/lodging/1000000/20000/18600/18535/eeef949f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/1000000/20000/18600/18535/ff71e235.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double or Twin Room, Garden View](https://images.trvl-media.com/lodging/1000000/20000/18600/18535/bfba6f62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winchester Royal Hotel [](https://www.expedia.ca/Winchester-Hotels-Winchester-Royal-Hotel.h18535.Hotel-Information) Winchester 8.4/10 Very good (1000) "Lovely clean room" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Jayne CA $167 CA $201 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Winchester-Hotels-Winchester-Royal-Hotel.h18535.Hotel-Information) ![Lunch and dinner served, international cuisine](https://images.trvl-media.com/lodging/1000000/10000/4800/4799/3ac6caac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/10000/4800/4799/c1f92a2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/1000000/10000/4800/4799/f5c213c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, soundproofing, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/10000/4800/4799/dbed426e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winchester Wessex Hotel by Sunday [](https://www.expedia.ca/Winchester-Hotels-Winchester-Wessex-Hotel-By-Sunday.h4799.Hotel-Information) Winchester 7.6/10 Good (1008) "Excellent staff service and great location of hotel" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Adam CA $107 CA $128 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Winchester-Hotels-Winchester-Wessex-Hotel-By-Sunday.h4799.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/5000000/4400000/4395300/4395298/04e7e74a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/5000000/4400000/4395300/4395298/abb48a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self parking](https://images.trvl-media.com/lodging/5000000/4400000/4395300/4395298/d36767fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4400000/4395300/4395298/36d3b4e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wykeham Arms [](https://www.expedia.ca/Winchester-Hotels-Wykeham-Arms.h4395298.Hotel-Information) Winchester 9.4/10 Exceptional (390) "Ideal place to stay for Winchester. So much so I should not be telling you about it. " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Douglas CA $206 CA $247 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Winchester-Hotels-Wykeham-Arms.h4395298.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2290000/2281600/2281514/9b5796f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room](https://images.trvl-media.com/lodging/3000000/2290000/2281600/2281514/af84305b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room](https://images.trvl-media.com/lodging/3000000/2290000/2281600/2281514/e48a09dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2290000/2281600/2281514/4ecf7017.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Westgate Winchester [](https://www.expedia.ca/Winchester-Hotels-Westgate-Winchester.h2281514.Hotel-Information) Winchester 8.2/10 Very good (244) "The staff made our stay amazing and the location can't be beat! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tricia CA $170 CA $205 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Winchester-Hotels-Westgate-Winchester.h2281514.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104530000/104521700/104521612/9f37fd6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104530000/104521700/104521612/46b660c6.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/105000000/104530000/104521700/104521612/bc0d0f96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104530000/104521700/104521612/ee350a31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rapunzel on Tower Stunning Period House in Central Winchester [](https://www.expedia.ca/Winchester-Hotels-Rapunzel-On-Tower-Stunning-Period-House-In-Central-Winchester.h104521612.Hotel-Information) Winchester 10/10 Exceptional (1) "Perfect location and layout for a family!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Casye M. CA $293 CA $523 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Winchester-Hotels-Rapunzel-On-Tower-Stunning-Period-House-In-Central-Winchester.h104521612.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/117000000/116100000/116099600/116099531/d2a39053.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/117000000/116100000/116099600/116099531/3de5128c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116100000/116099600/116099531/f410721d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/117000000/116100000/116099600/116099531/c95d5449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunday Winchester Wessex Cathedral Hotel | Compact [](https://www.expedia.ca/Winchester-Hotels-Sunday-Winchester-Wessex-Cathedral-Hotel-Compact.h116099531.Hotel-Information) Southampton CA $137 CA $137 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Winchester-Hotels-Sunday-Winchester-Wessex-Cathedral-Hotel-Compact.h116099531.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/117000000/116110000/116100900/116100858/e419fbec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/117000000/116110000/116100900/116100858/375b1564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/117000000/116110000/116100900/116100858/bcfb5431.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/117000000/116110000/116100900/116100858/d7bf1bfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunday Winchester Wessex Cathedral Hotel | Twin [](https://www.expedia.ca/Winchester-Hotels-Sunday-Winchester-Wessex-Cathedral-Hotel-Twin.h116100858.Hotel-Information) Winchester CA $176 CA $176 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Winchester-Hotels-Sunday-Winchester-Wessex-Cathedral-Hotel-Twin.h116100858.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/115000000/114480000/114476100/114476100/994ba05c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/115000000/114480000/114476100/114476100/69d568c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114480000/114476100/114476100/26334400.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/115000000/114480000/114476100/114476100/f21762e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunday Winchester Wessex Cathedral Hotel | Classic [](https://www.expedia.ca/Winchester-Hotels-Sunday-Winchester-Wessex-Cathedral-Hotel-Classic.h114476100.Hotel-Information) Winchester 6.0/10 (1) "Carpets and sofa in room were noticeably stained. Otherwise the view was great, bed was comfortable and clean. Staff were very helpful and professional " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Cathy CA $156 CA $156 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Winchester-Hotels-Sunday-Winchester-Wessex-Cathedral-Hotel-Classic.h114476100.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=2025-12-28&endDate=2025-12-29®ionId=5477&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![Leonardo Hotel Southampton ](https://images.trvl-media.com/lodging/2000000/1180000/1178300/1178290/0c96afed_y.jpg) ### Leonardo Hotel Southampton 10/10 Excellent "Nice room. Nice staff. Lewis was really friendly and made us feel welcome. He sorted out the missing hairdyer too. Give that man a pay rise!! " [](https://expedia.ca/Southampton-Hotels-Jurys-Inn-Southampton.h1178290.Hotel-Information) ![Holiday Inn Express Southampton M27 Jct7 by IHG](https://images.trvl-media.com/lodging/1000000/980000/977300/977282/fc514007_y.jpg) ### Holiday Inn Express Southampton M27 Jct7 by IHG 10/10 Excellent "Requested ground floor and got a great room on the ground level " [](https://expedia.ca/Southampton-Hotels-Holiday-Inn-Express-Southampton-M27-Jct7.h977282.Hotel-Information) ![Norton Park Hotel, Spa & Manor House](https://images.trvl-media.com/lodging/3000000/2780000/2773900/2773823/757d6db6_y.jpg) ### Norton Park Hotel, Spa & Manor House 10/10 Excellent "Ideal stay for Winchester or just a relaxing trip. The hotel is quite spread out so if disabled or can’t walk far I suggest asking for a room close to reception. Maintenance staff were fantastic. Cleaning staff great. Bar staff friendly. Highly recommend. Definitely going back. " [](https://expedia.ca/Winchester-Hotels-Norton-Park.h2773823.Hotel-Information) ![Novotel Southampton](https://images.trvl-media.com/lodging/1000000/10000/4500/4431/cebf2d75_y.jpg) ### Novotel Southampton 10/10 Excellent "Very friendly staff" [](https://expedia.ca/Southampton-Hotels-Novotel-Southampton.h4431.Hotel-Information) ![The Langstone Quays](https://images.trvl-media.com/lodging/1000000/10000/8600/8541/952fcd26_y.jpg) ### The Langstone Quays 10/10 Excellent "Room was immaculate, staff were friendly and polite. Breakfast was well presented and good quality" [](https://expedia.ca/Hayling-Island-Hotels-The-Langstone-Quays.h8541.Hotel-Information) ![The Winchester Hotel & Spa](https://images.trvl-media.com/lodging/1000000/30000/26100/26080/4127003a_y.jpg) ### The Winchester Hotel & Spa 10/10 Excellent "Friendly and helpful staff, comfy bed, lovely breakfast, great location and fabulous spa. " [](https://expedia.ca/Winchester-Hotels-The-Winchester-Hotel-Spa.h26080.Hotel-Information) ![Holiday Inn Portsmouth by IHG](https://images.trvl-media.com/lodging/1000000/30000/27200/27118/b7425f54_y.jpg) ### Holiday Inn Portsmouth by IHG 10/10 Excellent "Friendly staff, room clean and tidy. Good parking " [](https://expedia.ca/Portsmouth-Hotels-Holiday-Inn-Portsmouth.h27118.Hotel-Information) ![Leonardo Royal Southampton Grand Harbour](https://images.trvl-media.com/lodging/1000000/20000/20000/19955/662fccb6_y.jpg) ### Leonardo Royal Southampton Grand Harbour 10/10 Excellent "Hotel is very clean, facilities are great and all staff very friendly. The perfect 4 star experience. " [](https://expedia.ca/Southampton-Hotels-Leonardo-Royal-Southampton-Grand-Harbour.h19955.Hotel-Information) ![Winchester Wessex Hotel by Sunday](https://images.trvl-media.com/lodging/1000000/10000/4800/4799/3ac6caac_y.jpg) ### Winchester Wessex Hotel by Sunday 10/10 Excellent "Very friendly receptionist, great view of cathedral from our room and excellent location " [](https://expedia.ca/Winchester-Hotels-Winchester-Wessex-Hotel-By-Sunday.h4799.Hotel-Information) ## Frequently asked questions ### What should a history enthusiast expect from a trip to Winchester? ### How many historically relevant hotels are there in Winchester? ### What are the most important historical places and other sights in Winchester? ### What is a historic hotel like in Winchester? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Winchester have modern facilities? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - 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