Title: Winchester Chalets from CA $1,060 | Expedia.ca

  

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# Search Chalets in Winchester from CA $1,060

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## Check prices for these dates

In two weeks

[Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=5477&startDate=2025-10-24&endDate=2025-10-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=5477&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=5477&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[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)

## Browse Select Winchester Chalets

![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114340000/114330700/114330660/4ef694e0.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)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/115000000/114340000/114330700/114330660/3d0a7766.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/115000000/114340000/114330700/114330660/014c8369.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Creek View, Isle of Wight

Wootton Bridge

10/10

Exceptional

(1)

"So modern and spacious, clean and really comfy beds. Everything you could need. Loved the lights on the stairs! View from rear of house peaceful, loved watching the tides. Near brilliant bus route, every 10 mins. Good off road parking. Thanks also for the bottle of bubbly and gourous biscuits. Had issue with hot water, reported it and they had someone out to repair it just under 2 hours, wow, good customer service"

CA $2,648

CA $3,035 total

includes taxes & fees

Oct 9 - Oct 10

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

![Outdoor spa tub](https://images.trvl-media.com/lodging/114000000/113020000/113015600/113015528/bd238df1_edited_3def.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/114000000/113020000/113015600/113015528/fb982d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/114000000/113020000/113015600/113015528/0816d63d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/114000000/113020000/113015600/113015528/20d758a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dassia

Porchfield

9.6/10

Exceptional

(4)

"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."

CA $1,276

CA $1,498 total

includes taxes & fees

Oct 9 - Oct 10

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

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/67000000/66970000/66964300/66964247/225e4995.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)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/67000000/66970000/66964300/66964247/a5d9e70d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### No 1 Ashey

Ryde

9.4/10

Exceptional

(18)

"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."

CA $1,926

CA $2,250 total

includes taxes & fees

Oct 11 - Oct 12

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

![Exterior](https://images.trvl-media.com/lodging/67000000/66970000/66964300/66964240/5ea1fc55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/67000000/66970000/66964300/66964240/e31fba98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/67000000/66970000/66964300/66964240/4123f54c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/67000000/66970000/66964300/66964240/b9714a91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Middle Lodge

Ryde

9.4/10

Exceptional

(25)

"Great location with a rear garden gate which opens directly into Appley Park, which has a playground and runs down to the beach and sea. "

CA $1,625

CA $1,910 total

includes taxes & fees

Oct 9 - Oct 10

[](https://www.expedia.ca/Ryde-Hotels-Middle-Lodge.h66964240.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)

![Beach](https://images.trvl-media.com/lodging/113000000/112860000/112851000/112850957/c4577dc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/113000000/112860000/112851000/112850957/3418ac27_edited_57b6.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/cc471cea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Princes Esplanade

Gurnard

10/10

Exceptional

(2)

"the fantastic view Parking"

CA $1,216

CA $1,478 total

includes taxes & fees

Oct 9 - Oct 10

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

![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)

![Smart TV](https://images.trvl-media.com/lodging/22000000/21990000/21984200/21984165/e40369fb.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

Emsworth

9.6/10

Exceptional

(79)

"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."

CA $1,060

CA $1,060 total

includes taxes & fees

Nov 5 - Nov 6

[](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/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/90000000/89480000/89473500/89473416/183f234f.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)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/90000000/89480000/89473500/89473416/12dd235c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### York Street

Cowes

10/10

Exceptional

(8)

"It was absolutely perfect ! The house was so well looked after ."

CA $1,444

CA $1,692 total

includes taxes & fees

Oct 9 - Oct 10

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

![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114720000/114713500/114713493/4377ab14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/115000000/114720000/114713500/114713493/a1d54960.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114720000/114713500/114713493/6499c553.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/115000000/114720000/114713500/114713493/69ba4d22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Deck House, Isle of Wight

Gurnard

CA $1,252

CA $1,499 total

includes taxes & fees

Oct 9 - Oct 10

[](https://www.expedia.ca/Cowes-Hotels-The-Deck-House.h114713493.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/111290000/111288300/111288286/243392d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/112000000/111290000/111288300/111288286/71f153ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111290000/111288300/111288286/5a2d3126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111290000/111288300/111288286/439a4faf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### St Georges Villa

Ryde

CA $1,216

CA $1,422 total

includes taxes & fees

Oct 9 - Oct 10

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

![Exterior detail](https://images.trvl-media.com/lodging/110000000/109850000/109842800/109842731/3a908fb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/110000000/109850000/109842800/109842731/a043dd79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/110000000/109850000/109842800/109842731/88ea45cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/110000000/109850000/109842800/109842731/242b1188.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Driftwood House

Cowes

10/10

Exceptional

(2)

"Comfortably furnished, cute and cosy accommodation Pleasant garden Quiet location but very close to all local amenities, ferry port, etc Nice bedding, huge comfy duvet Great size kitchen diner Big TVs Modern clean kitchen appliances Milk, tea, coffee, sugar and cleaning products in kitchen on arrival Modern, clean shower rooms"

CA $963

CA $1,144 total

includes taxes & fees

Oct 10 - Oct 11

[](https://www.expedia.ca/Cowes-Hotels-Driftwood-House.h109842731.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/119000000/118840000/118833400/118833398/81e771e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/119000000/118840000/118833400/118833398/7c4d7cd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/119000000/118840000/118833400/118833398/eb42d4b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/119000000/118840000/118833400/118833398/e761ed6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Castle Cottage-Isle of Wight

Ryde

CA $1,083

CA $1,276 total

includes taxes & fees

Oct 7 - Oct 8

[](https://www.expedia.ca/Ryde-Hotels-Castle-Cottage.h118833398.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/115000000/114720000/114713500/114713495/2fe20052.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114720000/114713500/114713495/ebd36e9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/115000000/114720000/114713500/114713495/5df813ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/115000000/114720000/114713500/114713495/653952f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Penderic, Isle of Wight

Cowes

CA $1,252

CA $1,499 total

includes taxes & fees

Oct 9 - Oct 10

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

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/106000000/105360000/105351800/105351705/3be7dc26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/106000000/105360000/105351800/105351705/988b66eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### George Street House

Ryde

6.0/10

(1)

"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...

CA $1,396

CA $1,621 total

includes taxes & fees

Oct 31 - Nov 1

[](https://www.expedia.ca/Ryde-Hotels-George-Street-House.h105351705.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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## Top Winchester Hotel Reviews

![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

"Nothing of note"

[](https://expedia.ca/Southampton-Hotels-Holiday-Inn-Express-Southampton-M27-Jct7.h977282.Hotel-Information)

![Red Lion Hotel](//images.trvl-media.com/lodging/1000000/530000/520500/520493/1d095a16_y.jpg)

### Red Lion Hotel

10/10 Excellent

"Clean and convenient "

[](https://expedia.ca/Basingstoke-Hotels-Red-Lion-Hotel.h520493.Hotel-Information)

![voco Southampton by IHG](//images.trvl-media.com/lodging/1000000/20000/17500/17411/821a0cfd_y.jpg)

### voco Southampton by IHG

10/10 Excellent

"We stayed one night at this lovely hotel, I think it has recently had a refurb, our room was lovely and the bar/restaurant was great too, will definitely stay again"

[](https://expedia.ca/Southampton-Hotels-Voco-Southampton-By-IHG.h17411.Hotel-Information)

![Harbour Hotel Southampton](//images.trvl-media.com/lodging/20000000/19510000/19504400/19504324/68c45722_y.jpg)

### Harbour Hotel Southampton

10/10 Excellent

"Great hotel - minorities with TV guys sorted out fast! Would definitely stay again"

[](https://expedia.ca/Southampton-Hotels-Southampton-Harbour-Hotel.h19504324.Hotel-Information)

![Moxy Southampton](//images.trvl-media.com/lodging/43000000/42110000/42101700/42101688/92beb57c_y.jpg)

### Moxy Southampton

10/10 Excellent

"It was another great experience and the breakfast was good too and staff very pleasant and helpful."

[](https://expedia.ca/Southampton-Hotels-Moxy-By-Marriott-Southampton.h42101688.Hotel-Information)

![Leonardo Royal Southampton Grand Harbour](//images.trvl-media.com/lodging/1000000/20000/20000/19955/662fccb6_y.jpg)

### Leonardo Royal Southampton Grand Harbour

10/10 Excellent

"Great "

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

![Holiday Inn Portsmouth by IHG](//images.trvl-media.com/lodging/1000000/30000/27200/27118/b7425f54_y.jpg)

### Holiday Inn Portsmouth by IHG

10/10 Excellent

"Only complaint was we were a group so 3 rooms in total, one room was very cold and they were told the heating wasn't on yet and they didn't have any heaters available"

[](https://expedia.ca/Portsmouth-Hotels-Holiday-Inn-Portsmouth.h27118.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

"Staff were all very polite and kind. "

[](https://expedia.ca/Southampton-Hotels-Macdonald-Botley-Park-Hotel-Spa.h9369.Hotel-Information)

![New Place](//images.trvl-media.com/lodging/2000000/1590000/1587200/1587150/3b94f834_y.jpg)

### New Place

10/10 Excellent

"Have stayed at the hotel many times but decided this time to stay in the franklyn suite as a treat and wow it certainly did not disappoint ! "

[](https://expedia.ca/Southampton-Hotels-New-Place.h1587150.Hotel-Information)

## Find out more about Winchester

## Winchester Chalets information

| Number of reviews | 11 |
| --- | --- |
| Accommodation | 99 Chalets |
| Lowest Price | CA $1,060 |
| Highest Price | CA $3,035 |