Title: Winchester Vacation Rentals from CA $128: Short-Term Rentals for 2026 | Expedia.ca [Winchester Travel Guide](https://expedia.ca/Winchester.dx5477)[Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d5477.Travel-Guide-Hotels)[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) # 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 ## Check prices for these dates Tonight [Dec 11 - Dec 12](https://www.expedia.ca/Hotel-Search?regionId=5477&startDate=2025-12-11&endDate=2025-12-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=5477&startDate=2025-12-12&endDate=2025-12-13&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=5477&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=5477&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester vacation rentals ![Interior](https://images.trvl-media.com/lodging/122000000/121580000/121578100/121578063/ac1dd699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom](https://images.trvl-media.com/lodging/122000000/121580000/121578100/121578063/a7917cb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/122000000/121580000/121578100/121578063/eb25b28f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/122000000/121580000/121578100/121578063/94bb2b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aethelred Annexe - New Build with Full Amenities [](https://www.expedia.ca/Winchester-Hotels-Aethelred-Annexe-New-Build-With-Full-Amenities.h121578063.Hotel-Information) Winchester 10/10 Exceptional (1) "Had a lovely stay at the Aethelred Annexe! Great amenities and an incredibly generous host. It felt very warm and cozy and the bed was super comfy. Great location for a quick drive/ bus into the city centre. Would absolutely recommend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea W. CA $145 CA $174 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Winchester-Hotels-Aethelred-Annexe-New-Build-With-Full-Amenities.h121578063.Hotel-Information) ![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/119000000/118470000/118466000/118465980/ce79707a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/119000000/118470000/118466000/118465980/02e121d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118470000/118466000/118465980/w378h683x323y0-94174cf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/119000000/118470000/118466000/118465980/c136c0c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cosy A-Frame cabin nestled in the chalk steams of Hampshire [](https://www.expedia.ca/Winchester-Hotels-Cosy-A-Frame-Cabin-Nestled-In-The-Chalk-Steams-Of-Hampshire.h118465980.Hotel-Information) Winchester 9.4/10 Exceptional (3) "Lovely cabin and outside kitchen plus garden. It's my second stay and I enjoyed my stay. Love the garden kitchen,. It's very pretty and relaxing ." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Nicola H. CA $249 CA $335 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Winchester-Hotels-Cosy-A-Frame-Cabin-Nestled-In-The-Chalk-Steams-Of-Hampshire.h118465980.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) ![Living area](https://images.trvl-media.com/lodging/115000000/114100000/114092100/114092093/4087c90b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/115000000/114100000/114092100/114092093/85c606d5.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) ### Squirrel's Leap [](https://www.expedia.ca/Winchester-Hotels-Squirrels-Leap.h114092093.Hotel-Information) Winchester CA $721 CA $866 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Winchester-Hotels-Squirrels-Leap.h114092093.Hotel-Information) ![House (3 Bedrooms) | Terrace/patio](https://images.trvl-media.com/lodging/101000000/100960000/100955300/100955294/29bd57f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/101000000/100960000/100955300/100955294/a6fabf64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Private kitchen](https://images.trvl-media.com/lodging/101000000/100960000/100955300/100955294/cc5ef489.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100960000/100955300/100955294/b0149fdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Peaceful Elevated Residential Area - Walk to City [](https://www.expedia.ca/Winchester-Hotels-Peaceful-Elevated-Residential-Area-Walk-To-City.h100955294.Hotel-Information) Winchester CA $490 CA $588 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Winchester-Hotels-Peaceful-Elevated-Residential-Area-Walk-To-City.h100955294.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/123000000/122770000/122760500/122760442/6609e84a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/123000000/122770000/122760500/122760442/ac58521a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/123000000/122770000/122760500/122760442/64137664.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/123000000/122770000/122760500/122760442/b9e9e504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Hampshire at Mulberry Barn Annexe [](https://www.expedia.ca/Winchester-Hotels-Beautiful-Hampshire-At-Mulberry-Barn-Annexe.h122760442.Hotel-Information) Micheldever CA $221 CA $315 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Winchester-Hotels-Beautiful-Hampshire-At-Mulberry-Barn-Annexe.h122760442.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104280000/104279900/104279899/e7d986cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/105000000/104280000/104279900/104279899/d757ed50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104280000/104279900/104279899/4d8b14df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104280000/104279900/104279899/53b42fdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2-BR Cosy Retreat, w/ Garden, central Winchester [](https://www.expedia.ca/Winchester-Hotels-2-BR-Cosy-Retreat.h104279899.Hotel-Information) Winchester 8.0/10 Very good (2) "The property was excellent for location in Winchester and was very clean. The ‘garden’ is a small area of decking. " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) barbara [](https://www.expedia.ca/Winchester-Hotels-2-BR-Cosy-Retreat.h104279899.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882120/2ca8078e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882120/8e33df19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882120/81ff3273.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882120/bf8f8b04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Birdsong Mansion sleeps 12 Twyford Winchester [](https://www.expedia.ca/Winchester-Hotels-Birdsong-Mansion-Sleeps-12-Twyford-Winchester.h76882120.Hotel-Information) Winchester CA $1,836 CA $1,862 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Winchester-Hotels-Birdsong-Mansion-Sleeps-12-Twyford-Winchester.h76882120.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882133/8af8844f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882133/8260a4e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882133/b9f804d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882133/d2f5b779.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Birdsong House [](https://www.expedia.ca/Winchester-Hotels-Birdsong-House.h76882133.Hotel-Information) Winchester 10/10 Exceptional (1) "We had a wonderful stay at Birdsong house. The owner was always available and the house was so cozy and comfortable! Thank you" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Judith D. CA $1,446 CA $1,472 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Winchester-Hotels-Birdsong-House.h76882133.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) ![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) ![Miscellaneous](https://images.trvl-media.com/lodging/117000000/116100000/116099600/116099531/9c522b34.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) ### 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 2 - Jan 3, 2026 [](https://www.expedia.ca/Winchester-Hotels-Sunday-Winchester-Wessex-Cathedral-Hotel-Compact.h116099531.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/105000000/104530000/104521700/104521612/57f7814c.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 $324 CA $554 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) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119350000/119340100/119340066/bb8bbe76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/120000000/119350000/119340100/119340066/b3bbd15d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119350000/119340100/119340066/7c6a2147.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/120000000/119350000/119340100/119340066/w2245h1500x4y0-f616be12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Garden room, central Winchester [](https://www.expedia.ca/Winchester-Hotels-Garden-Room.h119340066.Hotel-Information) Winchester CA $166 CA $196 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Winchester-Hotels-Garden-Room.h119340066.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882122/6d5e54fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882122/06f9472d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882122/5da753a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882122/c0cc52cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Piping House 4bedroom [](https://www.expedia.ca/Winchester-Hotels-Piping-House-4bedroom.h76882122.Hotel-Information) Colden Common CA $492 CA $527 total includes taxes & fees Dec 13 - Dec 14 [](https://www.expedia.ca/Winchester-Hotels-Piping-House-4bedroom.h76882122.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) ![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) ![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/c8883c76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rivergem - Riverside Coach House [](https://www.expedia.ca/Winchester-Hotels-Rivergem-Riverside-Coach-House.h114343350.Hotel-Information) Winchester CA $847 CA $1,017 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Winchester-Hotels-Rivergem-Riverside-Coach-House.h114343350.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/90000000/89190000/89183300/89183237/0f155587.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89190000/89183300/89183237/5df8c4cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/90000000/89190000/89183300/89183237/178af1ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/90000000/89190000/89183300/89183237/9eee0bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Piping Green 4Bedroom House [](https://www.expedia.ca/Winchester-Hotels-Piping-Green-4Bedroom-House.h89183237.Hotel-Information) Colden Common CA $525 CA $560 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Winchester-Hotels-Piping-Green-4Bedroom-House.h89183237.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) ![Miscellaneous](https://images.trvl-media.com/lodging/117000000/116110000/116100900/116100858/d7bf1bfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/117000000/116110000/116100900/116100858/e08259e2.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) ### 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 2 - Jan 3, 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) ![Miscellaneous](https://images.trvl-media.com/lodging/115000000/114480000/114476100/114476100/f21762e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/115000000/114480000/114476100/114476100/a82d468b.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) ### 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) ![Marina](https://images.trvl-media.com/lodging/100000000/99940000/99932300/99932236/8fe76aa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/100000000/99940000/99932300/99932236/4c1a6eb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/100000000/99940000/99932300/99932236/cc369d36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99940000/99932300/99932236/5817dcd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 40 foot luxury yacht on 5\* Ocean Village Marina [](https://www.expedia.ca/Southampton-Hotels-40-Foot-Luxury-Yacht-On-5-Ocean-Village-Marina.h99932236.Hotel-Information) Southampton City Centre 10/10 Exceptional (2) "We decided to try something new instead of hotel so booked the yacht. Great experience. Marina and boat were lovely. Lots of restaurants and easy to walk around and explore. Steve and Miros went over and above to make sure our stay was great and even picked us up from cruise port and drove us to airport hotel the next day. Would highly recommend . " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Sheila CA $274 CA $387 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Southampton-Hotels-40-Foot-Luxury-Yacht-On-5-Ocean-Village-Marina.h99932236.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/96000000/95050000/95045500/95045482/4b86d2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/96000000/95050000/95045500/95045482/a0b72458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/96000000/95050000/95045500/95045482/a32d826a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/96000000/95050000/95045500/95045482/b4dd21bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful 4 Berth Boat on the Isle of Wight for the Ultimate Relaxation [](https://www.expedia.ca/Newport-Hotels-Beautiful-4-Berth-Boat-On-The-Isle-Of-Wight-For-The-Ultimate-Relaxation.h95045482.Hotel-Information) Binfield 10/10 Exceptional (1) "Best stay! Very new experience of staying in a boat. Amazing location for public services as well. " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) srini k. CA $313 CA $359 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Newport-Hotels-Beautiful-4-Berth-Boat-On-The-Isle-Of-Wight-For-The-Ultimate-Relaxation.h95045482.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/39000000/38730000/38725000/38724913/fc59aa41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38730000/38725000/38724913/c7de3214.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38730000/38725000/38724913/2ec62690.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/39000000/38730000/38725000/38724913/a8e8a432.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Y Knot - The New Way To Holiday [](https://www.expedia.ca/Lymington-Hotels-Y-Knot-The-New-Way-To-Holiday.h38724913.Hotel-Information) Lymington 9.4/10 Exceptional (3) "Agent failed to mention that the toilet was not to be used for number "two s" ." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) manojkunar P. CA $507 CA $584 total includes taxes & fees Dec 16 - Dec 17 [](https://www.expedia.ca/Lymington-Hotels-Y-Knot-The-New-Way-To-Holiday.h38724913.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) ![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) ![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) ### Stonehenge Cottages [](https://www.expedia.ca/Salisbury-Hotels-Stonehenge-Cottages.h9360141.Hotel-Information) Salisbury 9.8/10 Exceptional (105) "Information, including a video, provided by the friendly owners before and during our stay was excellent. The beautifully appointed cottage was convenient for Salisbury and for the nearby pub which serves good food. We will definitely stay there again, if in the area." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Fiona CA $260 CA $312 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Salisbury-Hotels-Stonehenge-Cottages.h9360141.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=2025-12-25&endDate=2025-12-26®ionId=5477&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%2FWinchester-Vacation-Rentals.d5477.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Vacation-Rentals.d5477.Travel-Guide-VacationRentals) ## Top Winchester Hotel Reviews ![Village Hotel Southampton Eastleigh](https://images.trvl-media.com/lodging/65000000/64270000/64264800/64264792/67cc524a_y.jpg) ### Village Hotel Southampton Eastleigh 10/10 Excellent "claen hotel reasonable price, good location" [](https://expedia.ca/Eastleigh-Hotels-Village-Hotel-Southampton-Eastleigh.h64264792.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) ![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) ![voco Southampton by IHG](https://images.trvl-media.com/lodging/1000000/20000/17500/17411/821a0cfd_y.jpg) ### voco Southampton by IHG 10/10 Excellent "Great room, great staff and lovely restaurant. Could t have met my expectations any better" [](https://expedia.ca/Southampton-Hotels-Voco-Southampton-By-IHG.h17411.Hotel-Information) ![Moxy Southampton](https://images.trvl-media.com/lodging/43000000/42110000/42101700/42101688/92beb57c_y.jpg) ### Moxy Southampton 10/10 Excellent "It’s was brilliant five star quality for me, breakfast plentiful excellent quality, thank you ⭐️⭐️⭐️⭐️⭐️" [](https://expedia.ca/Southampton-Hotels-Moxy-By-Marriott-Southampton.h42101688.Hotel-Information) ![DoubleTree by Hilton Southampton](https://images.trvl-media.com/lodging/1000000/20000/10400/10397/545dc144_y.jpg) ### DoubleTree by Hilton Southampton 10/10 Excellent "Had a lovely stay once again at the doubletree. Second year running to visit Winchester Christmas market. The staff were great and really accommodating. The facilities were perfect and breakfast had a great selection we all enjoyed " [](https://expedia.ca/Southampton-Hotels-DoubleTree-By-Hilton-Hotel-Southampton.h10397.Hotel-Information) ![voco Winchester Hotel & Spa by IHG](https://images.trvl-media.com/lodging/4000000/3440000/3430900/3430824/bec3fe8c_y.jpg) ### voco Winchester Hotel & Spa by IHG 10/10 Excellent "Stayed for one night to attend an event in central Winchester, which is a 10 minute drive away. The room itself was lovely and clean. The breakfast was excellent - lots of variety for all appetites and tastes. Was replenished regularly. Wouldn’t hesitate to stay again!" [](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester.h3430824.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 "Room spotless, staff couldn't do enough " [](https://expedia.ca/Southampton-Hotels-Holiday-Inn-Express-Southampton-M27-Jct7.h977282.Hotel-Information) ## Find out more about Winchester You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded. As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winchester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do. ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Winchester ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals ](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals ](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals ](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals ](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals ](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals ](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals ](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - [Palm Springs Vacation Rentals ](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals) - [Tofino Vacation Rentals ](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals) - [Calgary Vacation Rentals ](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals) - [Costa Rica Vacation Rentals ](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations) - [Vancouver Island Vacation Rentals ](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals) - [Puerto Vallarta Vacation Rentals ](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals) - [Hawaii Vacation Rentals ](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations) - [Toronto Vacation Rentals ](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals) - [Banff Vacation Rentals ](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals) - [Penticton Vacation Rentals ](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals) - [Osoyoos Vacation Rentals ](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals) - [Mont Tremblant Vacation Rentals ](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals) - [Big White Ski Resort Vacation Rentals ](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals) - [Ontario Vacation Rentals ](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations) - [British Columbia Vacation Rentals ](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations) - [Prince Edward Island Vacation Rentals ](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations) - [Québec Vacation Rentals ](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals) - [Apartments in Winchester ](https://expedia.ca/Winchester-Apartments.d5477-aaApartments.Travel-Guide-Accommodation) - [Cottages in Winchester ](https://expedia.ca/Winchester-Cottages.d5477-aaCottages.Travel-Guide-Accommodation) - [Vacation Homes in Winchester ](https://expedia.ca/Winchester-Private-Vacation-Homes.d5477-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Guest Houses in Winchester ](https://expedia.ca/Winchester-Guest-Houses.d5477-aaGuestHouses.Travel-Guide-Accommodation) - [Inns in Winchester ](https://expedia.ca/Winchester-Inns.d5477-aaInns.Travel-Guide-Accommodation) - [B&B in Winchester ](https://expedia.ca/Winchester-Bed-And-Breakfast.d5477-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Winchester ](https://expedia.ca/Winchester-Cabins.d5477-aaCabins.Travel-Guide-Accommodation) - [Aparthotels in Winchester ](https://expedia.ca/Winchester-Apart-Hotels.d5477-aaApartHotels.Travel-Guide-Accommodation) - [Houseboats in Winchester ](https://expedia.ca/Winchester-Houseboats.d5477-aaHouseboats.Travel-Guide-Accommodation) - [Farmstay in Winchester ](https://expedia.ca/Winchester-Agritourism.d5477-aaAgritourism.Travel-Guide-Accommodation) - [Holiday Park Resorts in Winchester ](https://expedia.ca/Winchester-Holiday-Parks.d5477-aaHolidayParks.Travel-Guide-Accommodation) - [Hostels in Winchester ](https://expedia.ca/Winchester-Hostels.d5477-aaHostels.Travel-Guide-Accommodation) - [Country Houses in Winchester ](https://expedia.ca/Winchester-Country-House.d5477-aaCountryHouse.Travel-Guide-Accommodation) ## Frequently asked questions ### Can I find vacation rentals in Winchester? ### What are some of the best vacation home rentals in Winchester? ### How many vacation rentals are there in Winchester? ### What’s there to see and do in Winchester? ### What’s a vacation rental in Winchester like? ### Expedia's Latest Trends Hotels - [Hotels in Bath](https://expedia.ca/Bath-Hotels.d6084496.Travel-Guide-Hotels) - [Hotels in Manchester](https://expedia.ca/Manchester-Hotels.d2205.Travel-Guide-Hotels) - [Hotels in Brighton](https://expedia.ca/Brighton-Hotels.d6046944.Travel-Guide-Hotels) - [Hotels in York](https://expedia.ca/York-Hotels.d5489.Travel-Guide-Hotels) - [Hotels in Oxford](https://expedia.ca/Oxford-Hotels.d9272.Travel-Guide-Hotels) - [Hotels in Southampton](https://expedia.ca/Southampton-Hotels.d3245.Travel-Guide-Hotels) Flights - [Flights to Southampton](https://expedia.ca/Cheap-Flights-To-Southampton.d3245.Travel-Guide-Flights) - [Flights to Leeds](https://expedia.ca/Cheap-Flights-To-Leeds.d6035434.Travel-Guide-Flights) - [Flights to Gatwick](https://expedia.ca/Cheap-Flights-To-Gatwick.d182523.Travel-Guide-Flights) - [Flights to Manchester](https://expedia.ca/Cheap-Flights-To-Manchester.d2205.Travel-Guide-Flights) - [Flights to Sale](https://expedia.ca/Cheap-Flights-To-Sale.d180178.Travel-Guide-Flights) Cars - [Car rentals in Gatwick](https://expedia.ca/Car-Rentals-In-Gatwick.d182523.Car-Rental-Guide) Activities - [Things to do in York](https://expedia.ca/Things-To-Do-In-York.d5489.Travel-Guide-Activities) - [Things to do in Sudbury](https://expedia.ca/Things-To-Do-In-Sudbury.d5705.Travel-Guide-Activities) - [Things to do in Gatwick](https://expedia.ca/Things-To-Do-In-Gatwick.d182523.Travel-Guide-Activities) - [Things to do in Bolton](https://expedia.ca/Things-To-Do-In-Bolton.d4576.Travel-Guide-Activities) - [Things to do in Scarborough](https://expedia.ca/Things-To-Do-In-Scarborough.d5680.Travel-Guide-Activities) - [Things to do in Whitby](https://expedia.ca/Things-To-Do-In-Whitby.d182692.Travel-Guide-Activities) - [Things to do in Bradford](https://expedia.ca/Things-To-Do-In-Bradford.d4981.Travel-Guide-Activities) - [Things to do in Southampton](https://expedia.ca/Things-To-Do-In-Southampton.d3245.Travel-Guide-Activities) - [Things to do in Manchester](https://expedia.ca/Things-To-Do-In-Manchester.d2205.Travel-Guide-Activities) - [Things to do in Keswick](https://expedia.ca/Things-To-Do-In-Keswick.d4371.Travel-Guide-Activities) General - [Visit Gloucester](https://expedia.ca/Gloucester.dx7479) - [Visit Goole](https://expedia.ca/Goole.dx6124778) - [Visit Scarborough](https://expedia.ca/Scarborough.dx5680) - [Visit Keswick](https://expedia.ca/Keswick.dx4371) - [Visit Exeter](https://expedia.ca/Exeter.dx1185) - [Visit Peterborough](https://expedia.ca/Peterborough.dx5655) - [Visit Northampton](https://expedia.ca/Northampton.dx9244) - [Visit Doncaster](https://expedia.ca/Doncaster.dx6822)