Title: Top Chalets in Winchester in 2026 | Expedia.co.uk [Winchester Travel Guide](https://expedia.co.uk/Winchester.dx5477)[Hotels in Winchester](https://expedia.co.uk/Winchester-Hotels.d5477.Travel-Guide-Hotels)[Holiday Rentals in Winchester](https://expedia.co.uk/Winchester-Holiday-Rentals.d5477.Travel-Guide-HolidayRentals)[Flights to Winchester](https://expedia.co.uk/Cheap-Flights-To-Winchester.d5477.Travel-Guide-Flights)[Things to do in Winchester](https://expedia.co.uk/Things-To-Do-In-Winchester.d5477.Travel-Guide-Activities)[Winchester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Winchester.d5477.Car-Hire-Guide)[Winchester Holidays](https://expedia.co.uk/Winchester.d5477.Holidays-City-Breaks) ![Winchester showing 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) ![](https://images.trvl-media.com/place/5477/36ffd968-a708-44fd-a530-107c0f9501f1.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 [10 Apr - 12 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=5477&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [22 May - 24 May](https://www.expedia.co.uk/Hotel-Search?regionId=5477&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [19 Jun - 21 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=5477&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [17 Jul - 19 Jul](https://www.expedia.co.uk/Hotel-Search?regionId=5477&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester chalets ![Exterior](https://images.trvl-media.com/lodging/90000000/89480000/89473500/89473416/2f205e3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/90000000/89480000/89473500/89473416/51ad4b27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/90000000/89480000/89473500/89473416/77de21d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/90000000/89480000/89473500/89473416/75f0b35c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### York Street [](https://www.expedia.co.uk/Cowes-Hotels-York-Street.h89473416.Hotel-Information) Cowes 10/10 Exceptional (8 reviews) "It was absolutely perfect ! The house was so well looked after ." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller £1,005 includes taxes & fees 8 Apr - 9 Apr [](https://www.expedia.co.uk/Cowes-Hotels-York-Street.h89473416.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114340000/114330700/114330660/b7433a03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/115000000/114340000/114330700/114330660/2fe4032a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/115000000/114340000/114330700/114330660/4aa4af78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/115000000/114340000/114330700/114330660/e1a6e230.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Creek View, Isle of Wight [](https://www.expedia.co.uk/Ryde-Hotels-Creek-View.h114330660.Hotel-Information) Wootton Bridge 10/10 Exceptional (3 reviews) "A truly amazing stay at a wonderful location. A superb home to base an island adventure! VRBO" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Benjamin Gully £1,483 includes taxes & fees 27 Mar - 28 Mar [](https://www.expedia.co.uk/Ryde-Hotels-Creek-View.h114330660.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/114000000/113020000/113015600/113015528/efd0ef58_edited_a803.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/114000000/113020000/113015600/113015528/777d1448.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113020000/113015600/113015528/e8bd5326.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/114000000/113020000/113015600/113015528/f783cfbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dassia [](https://www.expedia.co.uk/Cowes-Hotels-Dassia-Isle-Of-Wight.h113015528.Hotel-Information) Porchfield 9.6/10 Exceptional (4 reviews) "We stayed here over Christmas and it was perfect. Our dog loved the enclosed garden. The kitchen has everything to cook a festive dinner in. We had the log burner on for the day which was great. Would definitely stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emma £803 includes taxes & fees 25 Mar - 26 Mar [](https://www.expedia.co.uk/Cowes-Hotels-Dassia-Isle-Of-Wight.h113015528.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112860000/112851000/112850957/66c99deb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/113000000/112860000/112851000/112850957/f5ca605b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/113000000/112860000/112851000/112850957/210c8da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/113000000/112860000/112851000/112850957/df3b06c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Princes Esplanade [](https://www.expedia.co.uk/Cowes-Hotels-Princes-Esplanade-The-Isle-Of-Wight.h112850957.Hotel-Information) Gurnard 10/10 Exceptional (4 reviews) "We loved the beautiful location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan £803 includes taxes & fees 25 Mar - 26 Mar [](https://www.expedia.co.uk/Cowes-Hotels-Princes-Esplanade-The-Isle-Of-Wight.h112850957.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/67000000/66970000/66964300/66964247/255011c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/67000000/66970000/66964300/66964247/9c359852.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/67000000/66970000/66964300/66964247/7fc8b42b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/67000000/66970000/66964300/66964247/d3b82364.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### No 1 Ashey [](https://www.expedia.co.uk/Ryde-Hotels-No-1-Ashey.h66964247.Hotel-Information) Ryde 9.4/10 Exceptional (18 reviews) "We stayed here for three nights and loved it! The weather was amazing so we made the most out of the pool. The house is very clean and spacious." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller £1,226 includes taxes & fees 12 Apr - 13 Apr [](https://www.expedia.co.uk/Ryde-Hotels-No-1-Ashey.h66964247.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/22000000/21990000/21984200/21984165/c2af8a6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/22000000/21990000/21984200/21984165/12ec37ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/22000000/21990000/21984200/21984165/4407a401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/22000000/21990000/21984200/21984165/2085c5f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 6 Avocet Quay - a lodge/cabin that sleeps 4 guests in 2 bedrooms [](https://www.expedia.co.uk/Emsworth-Hotels-6-Avocet-Quay-A-Lodgecabin-That-Sleeps-4-Guests-In-2-Bedrooms.h21984165.Hotel-Information) Emsworth 9.6/10 Exceptional (81 reviews) "Booked for our friend's and family visit. Easy walk to Emsworth. Very well equipped and comfortable. Key collection instructions and updates were excellent. Would definitely stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caroline B. £699 includes taxes & fees 17 Apr - 18 Apr [](https://www.expedia.co.uk/Emsworth-Hotels-6-Avocet-Quay-A-Lodgecabin-That-Sleeps-4-Guests-In-2-Bedrooms.h21984165.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/106000000/105360000/105351800/105351705/1776cf70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105360000/105351800/105351705/3d38f5f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/106000000/105360000/105351800/105351705/fca0ee26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105360000/105351800/105351705/ac7db0c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### George Street House [](https://www.expedia.co.uk/Ryde-Hotels-George-Street-House.h105351705.Hotel-Information) Ryde 8.0/10 Very good (2 reviews) "Customer service was excellent with no problems, the process was vey efficient. The house was very clean and in a perfect spot for our stay, would highly recommend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kay £892 includes taxes & fees 27 Mar - 28 Mar [](https://www.expedia.co.uk/Ryde-Hotels-George-Street-House.h105351705.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/112000000/111290000/111288300/111288286/cd5a795f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111290000/111288300/111288286/161c4564.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111290000/111288300/111288286/f267e3a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/112000000/111290000/111288300/111288286/cddbf7cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### St Georges Villa [](https://www.expedia.co.uk/Ryde-Hotels-St-Georges-Villa-The-Isle-Of-Wight.h111288286.Hotel-Information) Ryde £786 includes taxes & fees 10 Apr - 11 Apr [](https://www.expedia.co.uk/Ryde-Hotels-St-Georges-Villa-The-Isle-Of-Wight.h111288286.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114720000/114713500/114713495/4863d010_edited_2ad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114720000/114713500/114713495/4d17d898.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114720000/114713500/114713495/cd06492b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114720000/114713500/114713495/5a0e708f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Penderic, Isle of Wight [](https://www.expedia.co.uk/Cowes-Hotels-Penderic.h114713495.Hotel-Information) Cowes £762 includes taxes & fees 20 Apr - 21 Apr [](https://www.expedia.co.uk/Cowes-Hotels-Penderic.h114713495.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.co.uk/Hotel-Search?startDate=2026-04-07&endDate=2026-04-08®ionId=5477&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find holiday rentals that suit your style Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom®ionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=APART_HOTEL) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom®ionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=APARTMENT) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom®ionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=VACATION_HOME) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom®ionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=COTTAGE) Residences [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom®ionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=RESIDENCE) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom®ionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=CONDO) Cabins [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom®ionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=CABIN) Chalets [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom®ionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=CHALET) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom®ionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=VILLA) Houseboats [](https://www.expedia.co.uk/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom®ionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-06-22&d1=2026-06-22&endDate=2026-06-25&d2=2026-06-25&lodging=HOUSE_BOAT) ![](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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Chalets.d5477-aaChalets.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Chalets.d5477-aaChalets.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![The Langstone Quays](https://images.trvl-media.com/lodging/1000000/10000/8600/8541/c15fb704_y.jpg) ### The Langstone Quays 8/10 Good "The room we stayed in was very close to the reception.We could hear people talking loudly which disturbed our sleep in more than one occasion.A sound proof door should be there between reception and the ground rooms to minimise or eliminate the sound.We also found dump in the bedroom walls, towards the main window and the bed sheets had holes on it." [](https://expedia.co.uk/Hayling-Island-Hotels-The-Langstone-Quays.h8541.Hotel-Information) ![Moxy Southampton](https://images.trvl-media.com/lodging/43000000/42110000/42101700/42101688/832abf4d_y.jpg) ### Moxy Southampton 10/10 Excellent "Was close enough to the bus stop to walk and close enough to the cruise port to walk. Forgot face cloths are not a thing a Europe…remember your fave cloths if traveling from North America. Hotel has a great vibe; staff were friendly and helpful. " [](https://expedia.co.uk/Southampton-Hotels-Moxy-By-Marriott-Southampton.h42101688.Hotel-Information) ![The Winchester Hotel & Spa](https://images.trvl-media.com/lodging/1000000/30000/26100/26080/0e859055_y.jpg) ### The Winchester Hotel & Spa 10/10 Excellent "Great" [](https://expedia.co.uk/Winchester-Hotels-The-Winchester-Hotel-Spa.h26080.Hotel-Information) ![Village Hotel Southampton Eastleigh](https://images.trvl-media.com/lodging/65000000/64270000/64264800/64264792/237f3bb5_y.jpg) ### Village Hotel Southampton Eastleigh 10/10 Excellent "The hotel is great value for money and has a great gym too. Free parking and affordable drinks at the bar." [](https://expedia.co.uk/Eastleigh-Hotels-Village-Hotel-Southampton-Eastleigh.h64264792.Hotel-Information) ![Leonardo Royal Southampton Grand Harbour](https://images.trvl-media.com/lodging/1000000/20000/20000/19955/f3b35638_y.jpg) ### Leonardo Royal Southampton Grand Harbour 10/10 Excellent "The room is clean, quiet. It is located in convenient location, only take 5 min walk to Tudor house & Garden, Westquay mall..etc. " [](https://expedia.co.uk/Southampton-Hotels-Leonardo-Royal-Southampton-Grand-Harbour.h19955.Hotel-Information) ![voco Winchester Hotel & Spa by IHG](https://images.trvl-media.com/lodging/4000000/3440000/3430900/3430824/dc660f41_y.jpg) ### voco Winchester Hotel & Spa by IHG 10/10 Excellent "Excellent internet " [](https://expedia.co.uk/Winchester-Hotels-Holiday-Inn-Winchester.h3430824.Hotel-Information) ![Village Hotel Portsmouth](https://images.trvl-media.com/lodging/20000000/19390000/19389300/19389255/14901ac6_y.jpg) ### Village Hotel Portsmouth 6/10 Okay "The hotel was noisy from 08:00 on Saturday morning with what I can only assume was a spin class being taken by someone using a mega-phone..." [](https://expedia.co.uk/Portsmouth-Hotels-Village-Hotel-Portsmouth.h19389255.Hotel-Information) ![Winchester Wessex Hotel by Sunday](https://images.trvl-media.com/lodging/1000000/10000/4800/4799/5efbbf93_y.jpg) ### Winchester Wessex Hotel by Sunday 10/10 Excellent "Nice stay" [](https://expedia.co.uk/Winchester-Hotels-Winchester-Wessex-Hotel-By-Sunday.h4799.Hotel-Information) ![Norton Park Hotel, Spa & Manor House](https://images.trvl-media.com/lodging/3000000/2780000/2773900/2773823/db967cc3_y.jpg) ### Norton Park Hotel, Spa & Manor House 10/10 Excellent "Great" [](https://expedia.co.uk/Winchester-Hotels-Norton-Park.h2773823.Hotel-Information) ## Find out more about Winchester ## Winchester Chalets information | Number of reviews | 8,275 | | ----------------- | ---------- | | Accommodation | 95 Chalets | | Lowest Price | £34 | | Highest Price | £180 | ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - [Apartments in Burley ](https://www.expedia.co.uk/Burley-Apartments.d182476-aaApartments.Travel-Guide-Accommodation) - 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