Title: Winchester Chalets from CA $1,424 | Expedia.ca

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![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)

![](https://images.trvl-media.com/place/5477/36ffd968-a708-44fd-a530-107c0f9501f1.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=5477&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=5477&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 10 - Apr 12](https://www.expedia.ca/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 four months

[May 8 - May 10](https://www.expedia.ca/Hotel-Search?regionId=5477&startDate=2026-05-08&endDate=2026-05-10&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

![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114340000/114330700/114330660/b7433a03.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)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/115000000/114340000/114330700/114330660/f4748b74.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)

### Chalet in Wootton Bridge

[](https://www.expedia.ca/Ryde-Hotels-Creek-View.h114330660.Hotel-Information)

10/10

Exceptional

(3 reviews)

"A truly amazing stay at a wonderful location. A superb home to base an island adventure! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Benjamin G.

CA $9,555

CA $10,631 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Ryde-Hotels-Creek-View.h114330660.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/90000000/89480000/89473500/89473416/2f205e3b.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)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/90000000/89480000/89473500/89473416/dab490c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Cowes

[](https://www.expedia.ca/Cowes-Hotels-York-Street.h89473416.Hotel-Information)

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

CA $1,612

CA $1,876 total

includes taxes & fees

Jan 19 - Jan 20

[](https://www.expedia.ca/Cowes-Hotels-York-Street.h89473416.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)

![Interior](https://images.trvl-media.com/lodging/114000000/113020000/113015600/113015528/4f1d59e2.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)

![TV, fireplace](https://images.trvl-media.com/lodging/114000000/113020000/113015600/113015528/777d1448.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Porchfield

[](https://www.expedia.ca/Cowes-Hotels-Dassia-Isle-Of-Wight.h113015528.Hotel-Information)

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

CA $1,266

CA $1,486 total

includes taxes & fees

Feb 14 - Feb 15

[](https://www.expedia.ca/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)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/113000000/112860000/112851000/112850957/ae40afd5.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)

### Chalet in Gurnard

[](https://www.expedia.ca/Cowes-Hotels-Princes-Esplanade-The-Isle-Of-Wight.h112850957.Hotel-Information)

10/10

Exceptional

(3 reviews)

"We loved the beautiful location"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Susan

CA $1,218

CA $1,480 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/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)

![Dining](https://images.trvl-media.com/lodging/67000000/66970000/66964300/66964247/d3b82364.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/67000000/66970000/66964300/66964247/6836a735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Ryde

[](https://www.expedia.ca/Ryde-Hotels-No-1-Ashey.h66964247.Hotel-Information)

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

CA $1,923

CA $2,246 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/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)

![Marina](https://images.trvl-media.com/lodging/22000000/21990000/21984200/21984165/2085c5f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/22000000/21990000/21984200/21984165/285ae35a.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)

### Chalet in Emsworth

[](https://www.expedia.ca/Emsworth-Hotels-6-Avocet-Quay-A-Lodgecabin-That-Sleeps-4-Guests-In-2-Bedrooms.h21984165.Hotel-Information)

9.6/10

Exceptional

(81 reviews)

"Can't say better than a return visit. Very comfortable base, with a beautiful balcony with views over the water and marsh. Lovely place to relax in the evening after a day exploring this beautiful part of the country."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Brodie S.

CA $1,458

CA $1,458 total

includes taxes & fees

Jan 18 - Jan 19

[](https://www.expedia.ca/Emsworth-Hotels-6-Avocet-Quay-A-Lodgecabin-That-Sleeps-4-Guests-In-2-Bedrooms.h21984165.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/cddbf7cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/112000000/111290000/111288300/111288286/48fc862c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Ryde

[](https://www.expedia.ca/Ryde-Hotels-St-Georges-Villa-The-Isle-Of-Wight.h111288286.Hotel-Information)

CA $1,218

CA $1,424 total

includes taxes & fees

Jan 16 - Jan 17

[](https://www.expedia.ca/Ryde-Hotels-St-Georges-Villa-The-Isle-Of-Wight.h111288286.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)

![Interior](https://images.trvl-media.com/lodging/106000000/105360000/105351800/105351705/53e04d22.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)

### Chalet in Ryde

[](https://www.expedia.ca/Ryde-Hotels-George-Street-House.h105351705.Hotel-Information)

6.0/10

(1 review)

"The property is spacious and is well placed for access to the town.However we found the lack of parking to be an added anxiety at the end of the day. Although told we could park in Co-op the signs said it closed with the shop at 8pm so we didn't risk it.Also the windows were extremely hard to open and close and didn't provide any noise reduction from the the very busy road. Buses ran until midnight and glazier and Co-op were both un/loading by 7am.We also had a ring doorbell go at 8.30 on 2...

![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg)

Karen R.

CA $1,385

CA $1,608 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Ryde-Hotels-George-Street-House.h105351705.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)

![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)

![TV](https://images.trvl-media.com/lodging/115000000/114720000/114713500/114713495/703ac993.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)

### Chalet in Cowes

[](https://www.expedia.ca/Cowes-Hotels-Penderic.h114713495.Hotel-Information)

CA $1,242

CA $1,488 total

includes taxes & fees

Feb 14 - Feb 15

[](https://www.expedia.ca/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.

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## Find vacation rentals that suit your style

Apartments

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Aparthotels

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Private vacation homes

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Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom&regionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=COTTAGE)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom&regionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=CABIN)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom&regionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=CHALET)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom&regionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=VILLA)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom&regionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=CONDO)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom&regionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=HOUSE_BOAT)

Residences

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+England%2C+United+Kingdom&regionId=5477&latLong=51.059776%2C-1.310146&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=RESIDENCE)

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## Top Winchester Hotel Reviews

![DoubleTree by Hilton Southampton](https://images.trvl-media.com/lodging/1000000/20000/10400/10397/545dc144_y.jpg)

### DoubleTree by Hilton Southampton

10/10 Excellent

"Great value for money. Very clean, quiet spacious rooms. Great hotel in the right location. Breakfast was five star. Couldn't fault the hotel at all."

[](https://expedia.ca/Southampton-Hotels-DoubleTree-By-Hilton-Hotel-Southampton.h10397.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

"Tiptop all round, lovely staff "

[](https://expedia.ca/Winchester-Hotels-Winchester-Wessex-Hotel-By-Sunday.h4799.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

"Really nice clean hotel with a decent size swimming pool for exercising in."

[](https://expedia.ca/Southampton-Hotels-Leonardo-Royal-Southampton-Grand-Harbour.h19955.Hotel-Information)

![Hilton Southampton - Utilita Bowl](https://images.trvl-media.com/lodging/10000000/9380000/9377900/9377882/69356af6_y.jpg)

### Hilton Southampton - Utilita Bowl

10/10 Excellent

"Great spa"

[](https://expedia.ca/Southampton-Hotels-Hilton-At-The-Ageas-Bowl-Southampton.h9377882.Hotel-Information)

![Leonardo Hotel Southampton ](https://images.trvl-media.com/lodging/2000000/1180000/1178300/1178290/0c96afed_y.jpg)

### Leonardo Hotel Southampton 

10/10 Excellent

"Spotless quiet room and comfortable bed"

[](https://expedia.ca/Southampton-Hotels-Jurys-Inn-Southampton.h1178290.Hotel-Information)

![Royal Maritime Hotel](https://images.trvl-media.com/lodging/16000000/15090000/15086700/15086665/8c64c9ac_y.jpg)

### Royal Maritime Hotel

10/10 Excellent

"Lovely clean room, friendly staff & good food.. stayed here twice now. "

[](https://expedia.ca/Portsmouth-Hotels-The-Royal-Maritime-Club.h15086665.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

"Beautifully hot"

[](https://expedia.ca/Winchester-Hotels-The-Winchester-Hotel-Spa.h26080.Hotel-Information)

![The Star Hotel](https://images.trvl-media.com/lodging/2000000/1230000/1223100/1223013/3d2213f7_y.jpg)

### The Star Hotel

10/10 Excellent

"Yes the room was very nice and clean and warm , nice hot shower . Bar wasn’t open but pub next door was ok , staff were very nice . "

[](https://expedia.ca/Southampton-Hotels-The-Star-Hotel.h1223013.Hotel-Information)

![Hotel du Vin & Bistro Winchester](https://images.trvl-media.com/lodging/8000000/7730000/7728500/7728491/04abd54d_y.jpg)

### Hotel du Vin & Bistro Winchester

10/10 Excellent

"Cost warm room and friendly welcoming staff. Would definitely stay here again !"

[](https://expedia.ca/Winchester-Hotels-Hotel-Du-Vin-Bistro-Winchester.h7728491.Hotel-Information)

## Find out more about Winchester

## Winchester Chalets information

| Number of reviews | 10         |
| ----------------- | ---------- |
| Accommodation     | 95 Chalets |
| Lowest Price      | CA $1,424  |
| Highest Price     | CA $10,631 |