Title: City of Winchester Vacation Rentals from CA $139: Short-Term Rentals for 2025 | Expedia.ca [City of Winchester Hotels](https://expedia.ca/Destinations-In-City-Of-Winchester.d553248635976006030.Hotel-Destinations)[City of Winchester Car Rentals](https://expedia.ca/Destinations-In-City-Of-Winchester.d553248635976006030.Car-Rental-Destinations)[City of Winchester Vacations](https://expedia.ca/City-Of-Winchester.d553248635976006030.Destination-Travel-Guides) ![Great Hall which includes signage](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/126000/126758-Winchester.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # City of Winchester 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 ## Top Cities in City of Winchester ![Southampton which includes château or palace, heritage elements and heritage architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/58000/58882-Southampton.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Southampton [](https://expedia.ca/Southampton-Vacation-Rentals.d3245.Travel-Guide-VacationRentals) ![Winchester featuring heritage architecture and a fountain](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/126000/126817-Winchester.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Winchester [](https://expedia.ca/Winchester-Vacation-Rentals.d5477.Travel-Guide-VacationRentals) ## Top Vacation Rentals in in City of Winchester ![Chalet, Garden View | Living area](https://images.trvl-media.com/lodging/121000000/120400000/120393800/120393715/00823c42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chalet, Garden View | Living area](https://images.trvl-media.com/lodging/121000000/120400000/120393800/120393715/e189127b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chalet, Garden View](https://images.trvl-media.com/lodging/121000000/120400000/120393800/120393715/b9b0417c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chalet, Garden View | Bathroom](https://images.trvl-media.com/lodging/121000000/120400000/120393800/120393715/fcb9a316.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hugo Stable- Cozy get away Waterlooville CA $175 CA $265 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Waterlooville-Hotels-The-Hugo-Stable-Cozy-Get-Away.h120393715.Hotel-Information) ![Apartment, 1 Bedroom, Patio, Garden View | Living area](https://images.trvl-media.com/lodging/121000000/120140000/120140000/120139981/20a6562e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/121000000/120140000/120140000/120139981/9bb6c8b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom, Patio, Garden View](https://images.trvl-media.com/lodging/121000000/120140000/120140000/120139981/1d1d6757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom, Patio, Garden View | Living area](https://images.trvl-media.com/lodging/121000000/120140000/120140000/120139981/50e82aab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rudley Ranch Waterlooville CA $194 CA $288 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Waterlooville-Hotels-Rudley-Ranch.h120139981.Hotel-Information) ![Apartment, Garden View](https://images.trvl-media.com/lodging/121000000/120620000/120614400/120614312/7f7f074c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120620000/120614400/120614312/a5ba39e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120620000/120614400/120614312/c427eb1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, Garden View](https://images.trvl-media.com/lodging/121000000/120620000/120614400/120614312/52a734f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Riley Stable- Cozy Getaway Waterlooville CA $194 CA $288 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Waterlooville-Hotels-The-Riley-Stable-Cozy-Getaway.h120614312.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/115000000/114100000/114092100/114092093/61d2ed89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, dishwasher, electric kettle, toaster](https://images.trvl-media.com/lodging/115000000/114100000/114092100/114092093/c372ed78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/115000000/114100000/114092100/114092093/4139ec3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/115000000/114100000/114092100/114092093/4087c90b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Squirrel's Leap Winchester CA $724 CA $869 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Winchester-Hotels-Squirrels-Leap.h114092093.Hotel-Information) ![Fridge, dishwasher, electric kettle, toaster](https://images.trvl-media.com/lodging/88000000/87730000/87725300/87725238/eba59246.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/88000000/87730000/87725300/87725238/6ae04938.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/88000000/87730000/87725300/87725238/e261e503.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/88000000/87730000/87725300/87725238/e6bd7c22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Barley Cottage Alresford CA $1,061 CA $1,274 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Alresford-Hotels-Barley-Cottage.h87725238.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114350000/114343400/114343350/4d3192ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114350000/114343400/114343350/9b26f142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/115000000/114350000/114343400/114343350/00916ced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, individually decorated, individually furnished, free WiFi](https://images.trvl-media.com/lodging/115000000/114350000/114343400/114343350/f2203821.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rivergem - Riverside Coach House Winchester [](https://www.expedia.ca/Winchester-Hotels-Rivergem-Riverside-Coach-House.h114343350.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/104000000/103490000/103487900/103487847/0b18ef56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/104000000/103490000/103487900/103487847/402c06c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/104000000/103490000/103487900/103487847/03616ef1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Video-game console](https://images.trvl-media.com/lodging/104000000/103490000/103487900/103487847/f10e2304.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coppice Hill House Southampton CA $1,833 CA $2,200 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Southampton-Hotels-Coppice-Hill-House.h103487847.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114110000/114104600/114104583/07a9bb5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, individually decorated, individually furnished, free WiFi](https://images.trvl-media.com/lodging/115000000/114110000/114104600/114104583/d3c4a885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/115000000/114110000/114104600/114104583/be6348b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/115000000/114110000/114104600/114104583/2d3060ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Suetts Farm Barns Southampton CA $1,263 CA $1,516 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Southampton-Hotels-Suetts-Farm-Barns.h114104583.Hotel-Information) ![Luxury Suite, Ensuite | Private kitchen](https://images.trvl-media.com/lodging/10000000/9370000/9360200/9360141/f5b45b40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, Ensuite | Private kitchen](https://images.trvl-media.com/lodging/10000000/9370000/9360200/9360141/14bd7196.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9370000/9360200/9360141/1f30f09c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, Ensuite](https://images.trvl-media.com/lodging/10000000/9370000/9360200/9360141/778e4cc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stonehenge Cottages Salisbury 9.8/10 Exceptional (105) "The property is beautifully designed. It is compact but well planned out and very tasteful. Everything you need is there. The breakfast basket is delightful! The cottage is attractive and in a lovely location. It is so easy to just walk across the road for dinner. We loved it!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ian CA $260 CA $312 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Salisbury-Hotels-Stonehenge-Cottages.h9360141.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/23000000/22610000/22608700/22608660/884f1de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee shop](https://images.trvl-media.com/lodging/23000000/22610000/22608700/22608660/305cd3c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/23000000/22610000/22608700/22608660/4b40b014.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Master Loft](https://images.trvl-media.com/lodging/23000000/22610000/22608700/22608660/c5b15fb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### room2 Southampton Hometel Southampton City Centre 9.4/10 Exceptional (1151) "staff was very friendly and rooms we clean and comfortable " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Kathy CA $116 CA $139 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Southampton-Hotels-Room2-Southampton.h22608660.Hotel-Information) ![Fridge, electric kettle, toaster, cookware/dishes/utensils](https://images.trvl-media.com/lodging/115000000/114100000/114094200/114094145/41985bb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, individually decorated, individually furnished, free WiFi](https://images.trvl-media.com/lodging/115000000/114100000/114094200/114094145/0e963b63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114100000/114094200/114094145/029e68dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/115000000/114100000/114094200/114094145/5402b7d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mutley Hall Chichester 10/10 Exceptional (1) "Lovely little cottage,very clean,parking,private,little gem" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) john CA $442 CA $530 total includes taxes & fees Nov 28 - Nov 29 [](https://www.expedia.ca/Chichester-Hotels-Mutley-Hall.h114094145.Hotel-Information) ![Studio, 1 Queen Bed | Private kitchen](https://images.trvl-media.com/lodging/14000000/13060000/13055800/13055764/7eeb8287.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/14000000/13060000/13055800/13055764/127852ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Apartment | Living area](https://images.trvl-media.com/lodging/14000000/13060000/13055800/13055764/a24255e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business Apartment](https://images.trvl-media.com/lodging/14000000/13060000/13055800/13055764/8fb9cc50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peartree Serviced Apartments Salisbury 9.6/10 Exceptional (295) "The place was right around the corner of rail station, so easy to get to. Was quiet for being so near to railway. The free laundry set up was very convenient; even provided detergent. Would stay there again. Thank you." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brenda CA $133 CA $160 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Salisbury-Hotels-Peartree-Serviced-Apartments.h13055764.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/38000000/37800000/37797500/37797465/a96c7f20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Cottage, 2 Bedrooms, Non Smoking, Lakeside | Private kitchen](https://images.trvl-media.com/lodging/38000000/37800000/37797500/37797465/2b9ccbd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Chalet, 1 Double Bed, Partial Lake View](https://images.trvl-media.com/lodging/38000000/37800000/37797500/37797465/2216d546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water view](https://images.trvl-media.com/lodging/38000000/37800000/37797500/37797465/bb4f2ea2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Northlands Farm & Lakes Chichester 9.2/10 Wonderful (42) "A really lovely weekend break - Chalet 2 is perfect, the farm and location is so nice too - would recommend." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Sara CA $238 CA $286 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chichester-Hotels-Northlands-Farm-Lakes-Premium-Chalet-1.h37797465.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/4000000/3970000/3963500/3963451/bfa5493b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3970000/3963500/3963451/8d72b2e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/4000000/3970000/3963500/3963451/4e3158fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/4000000/3970000/3963500/3963451/6a60fc8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### HQ Aparthotel Farnborough Rushmoor District 9.0/10 Wonderful (443) "As always, excellent friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter CA $118 CA $141 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Farnborough-Hotels-SACO-Aparthotel-Farnborough.h3963451.Hotel-Information) ![Apartment | Private kitchen](https://images.trvl-media.com/lodging/106000000/105540000/105532100/105532002/e3154997.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | Dining](https://images.trvl-media.com/lodging/106000000/105540000/105532100/105532002/dfd802ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment | Property grounds](https://images.trvl-media.com/lodging/106000000/105540000/105532100/105532002/8d8b315e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment](https://images.trvl-media.com/lodging/106000000/105540000/105532100/105532002/efc75f50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Bed Flat - Sleeps 4 - Parking - Wifi The Polygon 10/10 Exceptional (1) "Great apartment, super friendly host!" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Amy CA $429 CA $515 total includes taxes & fees Dec 9 - Dec 10 [](https://www.expedia.ca/Southampton-Hotels-Charming-2-Bed-Apartment-In-Central-Southampton.h105532002.Hotel-Information) ![House, 3 Bedrooms, Lake View | Interior](https://images.trvl-media.com/lodging/122000000/121410000/121410000/121409958/5f3c57d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 3 Bedrooms, Lake View | Bathroom](https://images.trvl-media.com/lodging/122000000/121410000/121410000/121409958/c102b494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living room](https://images.trvl-media.com/lodging/122000000/121410000/121410000/121409958/f32db6a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, 3 Bedrooms, Lake View](https://images.trvl-media.com/lodging/122000000/121410000/121410000/121409958/be6dcee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning Holiday Home Beautiful Lakeside Views 15 Mins From Goodwood Chichester CA $146 CA $175 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chichester-Hotels-Holiday-Home-Lakeside-Views-15-Mins-To-Goodwood.h121409958.Hotel-Information) ![Family Apartment | Living area](https://images.trvl-media.com/lodging/110000000/109070000/109065200/109065173/acdc998e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Apartment](https://images.trvl-media.com/lodging/110000000/109070000/109065200/109065173/492a91f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109070000/109065200/109065173/c81f3045.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Apartment | Private kitchen](https://images.trvl-media.com/lodging/110000000/109070000/109065200/109065173/b773b2bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charles Hope Salisbury Centre Salisbury 9.6/10 Exceptional (4) "Great location and well appointed apartment" ![Australia](https://a.travel-assets.com/egds/marks/flags/au.svg) Greg [](https://www.expedia.ca/Salisbury-Hotels-Charles-Hope-Salisbury-Centre.h109065173.Hotel-Information) ![House | Living area](https://images.trvl-media.com/lodging/47000000/46080000/46071300/46071263/dd2b2a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shopping mall](https://images.trvl-media.com/lodging/47000000/46080000/46071300/46071263/1c62bbc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | Private kitchen](https://images.trvl-media.com/lodging/47000000/46080000/46071300/46071263/d9ec14c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House](https://images.trvl-media.com/lodging/47000000/46080000/46071300/46071263/bcb3f728.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Somers House Portsmouth 10/10 Exceptional (1) "Very close to train station. Very close to large grocery store. Many diverse take-away and dining options in the neighbourhood. We all had our own bedroom. Kitchen was well equipped. Instructions for entry were clear. Door key was tricky at first, but we got the hang of it eventually. Bus routes nearby. No complaints. Would not hesitate to book again. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Catherine [](https://www.expedia.ca/Portsmouth-Hotels-Somers-House.h46071263.Hotel-Information) ![Cottage, Private Bathroom | Private kitchen](https://images.trvl-media.com/lodging/12000000/11850000/11845500/11845445/f93d7e9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, Private Bathroom | Lounge](https://images.trvl-media.com/lodging/12000000/11850000/11845500/11845445/a4eab255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, Private Bathroom](https://images.trvl-media.com/lodging/12000000/11850000/11845500/11845445/5495924a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, Private Bathroom | Private kitchen](https://images.trvl-media.com/lodging/12000000/11850000/11845500/11845445/da853c5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Meadow Cottage Salisbury 10/10 Exceptional (4) "Perfect for our needs, well furnished, comfortable and lovely walk across the water meadows into town (approx 15-20 mins)" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Colin CA $334 CA $401 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Salisbury-Hotels-Meadow-Cottage.h11845445.Hotel-Information) ![Cottage | Interior](https://images.trvl-media.com/lodging/45000000/44520000/44511300/44511291/a131954d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Living room](https://images.trvl-media.com/lodging/45000000/44520000/44511300/44511291/23783503.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Interior](https://images.trvl-media.com/lodging/45000000/44520000/44511300/44511291/4fd3e277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage | Exterior](https://images.trvl-media.com/lodging/45000000/44520000/44511300/44511291/f030846b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5 Yarmouth Cottages Freshwater 9.4/10 Exceptional (3) "Convenient and spotlessly clean small cottage is a great base for exploring the IoW. Only slight downside is that the proximity to other guests means sitting outside can be a little bit of an exercise in hearing other people’s conversation! This small point aside, can recommend for a short stay. " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Clive CA $496 CA $595 total includes taxes & fees Nov 22 - Nov 23 [](https://www.expedia.ca/Freshwater-Hotels-5-Yarmouth-Cottages.h44511291.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=2025-11-22&endDate=2025-11-23®ionId=553248635976006030&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&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%2FDestinations-In-City-Of-Winchester.d553248635976006030.Vacation-Rental-Destinations)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-City-Of-Winchester.d553248635976006030.Vacation-Rental-Destinations) ## Top City of Winchester Hotel Reviews ![voco Winchester Hotel & Spa by IHG](//images.trvl-media.com/lodging/4000000/3440000/3430900/3430824/bec3fe8c_y.jpg) ### voco Winchester Hotel & Spa by IHG 10/10 Excellent "Great" [](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester.h3430824.Hotel-Information) ![Leonardo Hotel Southampton ](//images.trvl-media.com/lodging/2000000/1180000/1178300/1178290/0c96afed_y.jpg) ### Leonardo Hotel Southampton 10/10 Excellent "clean room and friendly staff. Central location and quiet. Good breakfast selection " [](https://expedia.ca/Southampton-Hotels-Jurys-Inn-Southampton.h1178290.Hotel-Information) ![Macdonald Botley Park Hotel & Spa](//images.trvl-media.com/lodging/1000000/10000/9400/9369/4a8e2deb_y.jpg) ### Macdonald Botley Park Hotel & Spa 10/10 Excellent "Great customer service on check in. Friendly and helpful. Room clean and comfortable." [](https://expedia.ca/Southampton-Hotels-Macdonald-Botley-Park-Hotel-Spa.h9369.Hotel-Information) ![Moxy Southampton](//images.trvl-media.com/lodging/43000000/42110000/42101700/42101688/92beb57c_y.jpg) ### Moxy Southampton 10/10 Excellent "No" [](https://expedia.ca/Southampton-Hotels-Moxy-By-Marriott-Southampton.h42101688.Hotel-Information) ![Harbour Hotel Southampton](//images.trvl-media.com/lodging/20000000/19510000/19504400/19504324/68c45722_y.jpg) ### Harbour Hotel Southampton 10/10 Excellent "Beautiful hotel.Lovely staff .Super rooms and incredibly clean." [](https://expedia.ca/Southampton-Hotels-Southampton-Harbour-Hotel.h19504324.Hotel-Information) ![ORIDA Hotels Newbury](//images.trvl-media.com/lodging/1000000/530000/520500/520436/a58786b7_y.jpg) ### ORIDA Hotels Newbury 10/10 Excellent "Nice clean, comfortable room, a little worn and dated but a pleasant stay. Breakfast was nice with plenty of choice." [](https://expedia.ca/Newbury-Hotels-Orida-Newbury.h520436.Hotel-Information) ![Holiday Inn Express Southampton M27 Jct7 by IHG](//images.trvl-media.com/lodging/1000000/980000/977300/977282/fc514007_y.jpg) ### Holiday Inn Express Southampton M27 Jct7 by IHG 10/10 Excellent "I was visiting from the United States. The hotel was very nice. The front desk staff was excellent getting us a taxi to the port. There was only one gentleman who had not a very nice attitude and he worked at the bar, tall white guy. I had a handicap room that I did not care for, but that was all that was available when I checked in overall The hotel was nice." [](https://expedia.ca/Southampton-Hotels-Holiday-Inn-Express-Southampton-M27-Jct7.h977282.Hotel-Information) ![The Winchester Hotel & Spa](//images.trvl-media.com/lodging/1000000/30000/26100/26080/4127003a_y.jpg) ### The Winchester Hotel & Spa 10/10 Excellent "Fantastic stay" [](https://expedia.ca/Winchester-Hotels-The-Winchester-Hotel-Spa.h26080.Hotel-Information) ![The Hog's Back Hotel & Spa Farnham](//images.trvl-media.com/lodging/1000000/40000/34400/34344/8245c463_y.jpg) ### The Hog's Back Hotel & Spa Farnham 10/10 Excellent "Nice convenient location for a family catch up" [](https://expedia.ca/Farnham-Hotels-The-Hogs-Back-Hotel-Spa-Farnham.h34344.Hotel-Information) ## Find out more about City of Winchester **Everything you need to know about** **City of Winchester** **vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the City of Winchester vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect City of Winchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **City of Winchester vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in City of Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A City of Winchester vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of City of Winchester vacation rentals we have selected for you start as low as CA $139 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on City of Winchester rentals** At Expedia, we put the best City of Winchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top City of Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream City of Winchester vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around City of Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## Explore a world of travel with Expedia - Popular City of Winchester Cities - [Winchester Vacation Rentals](https://expedia.ca/Winchester-Vacation-Rentals.d5477.Travel-Guide-VacationRentals)