Title: Winchester Vacation Rentals from CA $92: Short-Term Rentals for 2026 | 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

[Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=5477&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=5477&startDate=2026-03-27&endDate=2026-03-29&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=5477&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[May 22 - May 24](https://www.expedia.ca/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)

## Our top choices for Winchester vacation rentals

![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)

![Interior](https://images.trvl-media.com/lodging/122000000/121580000/121578100/121578063/ac1dd699.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121580000/121578100/121578063/c79deb60.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 review)

"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 $151

CA $181 total

includes taxes & fees

Jan 30 - Jan 31

[](https://www.expedia.ca/Winchester-Hotels-Aethelred-Annexe-New-Build-With-Full-Amenities.h121578063.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/119000000/118470000/118466000/118465980/w1024h680x0y0-2826f4df.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/c136c0c5.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)

### 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

9.0/10

Wonderful

(4 reviews)

"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 $303

CA $396 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Winchester-Hotels-Cosy-A-Frame-Cabin-Nestled-In-The-Chalk-Steams-Of-Hampshire.h118465980.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)

![Dining](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882133/b48ff27b.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 review)

"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 $1,467

CA $1,493 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Winchester-Hotels-Birdsong-House.h76882133.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)

![Living area](https://images.trvl-media.com/lodging/115000000/114100000/114092100/114092093/334cfc10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/115000000/114100000/114092100/114092093/ffa00035.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 $766

CA $919 total

includes taxes & fees

Jan 31 - Feb 1

[](https://www.expedia.ca/Winchester-Hotels-Squirrels-Leap.h114092093.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882120/81ff3273.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882120/0fb958ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882120/7f31934a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![8 bedrooms, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882120/ee9207f2.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 $1,863

CA $1,889 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Winchester-Hotels-Birdsong-Mansion-Sleeps-12-Twyford-Winchester.h76882120.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116100000/116099600/116099531/b283f83d.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/117000000/116100000/116099600/116099531/5433d693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Golf](https://images.trvl-media.com/lodging/117000000/116100000/116099600/116099531/c95d5449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/117000000/116100000/116099600/116099531/e7adf6ee.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 $124

CA $124 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Winchester-Hotels-Sunday-Winchester-Wessex-Cathedral-Hotel-Compact.h116099531.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/90000000/89190000/89183300/89183237/d22e552e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89190000/89183300/89183237/b1fc34ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89190000/89183300/89183237/e55f5143.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)

### Piping Green 4Bedroom House

[](https://www.expedia.ca/Winchester-Hotels-Piping-Green-4Bedroom-House.h89183237.Hotel-Information)

Colden Common

CA $533

CA $568 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Winchester-Hotels-Piping-Green-4Bedroom-House.h89183237.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)

![Dining](https://images.trvl-media.com/lodging/105000000/104280000/104279900/104279899/138df0bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/105000000/104280000/104279900/104279899/0f95084f.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/ac72ac24.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 reviews)

"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

CA $277

CA $510 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Winchester-Hotels-2-BR-Cosy-Retreat.h104279899.Hotel-Information)

![4 bedrooms, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882122/b263005b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882122/64ec86b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882122/d3c67c86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/77000000/76890000/76882200/76882122/6d5e54fe.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 $499

CA $535 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Winchester-Hotels-Piping-House-4bedroom.h76882122.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)

![Miscellaneous](https://images.trvl-media.com/lodging/120000000/119350000/119340100/119340066/4b5e5023.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)

### Garden room, central Winchester

[](https://www.expedia.ca/Winchester-Hotels-Garden-Room.h119340066.Hotel-Information)

Winchester

CA $168

CA $198 total

includes taxes & fees

Jan 31 - Feb 1

[](https://www.expedia.ca/Winchester-Hotels-Garden-Room.h119340066.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/117000000/116110000/116100900/116100858/76a834c6.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)

![Miscellaneous](https://images.trvl-media.com/lodging/117000000/116110000/116100900/116100858/f5fcb3b5.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 $144

CA $144 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Winchester-Hotels-Sunday-Winchester-Wessex-Cathedral-Hotel-Twin.h116100858.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/efb6cc86.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)

![Living area](https://images.trvl-media.com/lodging/115000000/114350000/114343400/114343350/00916ced.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 $1,347

CA $1,617 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Winchester-Hotels-Rivergem-Riverside-Coach-House.h114343350.Hotel-Information)

![Spa](https://images.trvl-media.com/lodging/96000000/95050000/95045500/95045482/b4dd21bb.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)

![Interior](https://images.trvl-media.com/lodging/96000000/95050000/95045500/95045482/f5936e63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/96000000/95050000/95045500/95045482/4b86d2ba.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 review)

"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 $318

CA $361 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Newport-Hotels-Beautiful-4-Berth-Boat-On-The-Isle-Of-Wight-For-The-Ultimate-Relaxation.h95045482.Hotel-Information)

![Cottage | Balcony](https://images.trvl-media.com/lodging/60000000/59650000/59649900/59649802/ba3187d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage](https://images.trvl-media.com/lodging/60000000/59650000/59649900/59649802/5ad4e1e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage | Balcony](https://images.trvl-media.com/lodging/60000000/59650000/59649900/59649802/c1129aed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/60000000/59650000/59649900/59649802/2bea1fb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Groomes Country House

[](https://www.expedia.ca/Bordon-Hotels-Groomes-Country-House.h59649802.Hotel-Information)

Bordon

CA $4,842

CA $5,810 total

includes taxes & fees

Jan 29 - Jan 30

[](https://www.expedia.ca/Bordon-Hotels-Groomes-Country-House.h59649802.Hotel-Information)

![House, Accessible, Ensuite (Farmhouse) | Exterior](https://images.trvl-media.com/lodging/3000000/2240000/2236200/2236109/341a5785.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Accessible, Ensuite (Farmhouse) | Exterior](https://images.trvl-media.com/lodging/3000000/2240000/2236200/2236109/a090076b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Accessible, Ensuite (Farmhouse) | Lounge](https://images.trvl-media.com/lodging/3000000/2240000/2236200/2236109/af2404f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Accessible, Ensuite (Farmhouse)](https://images.trvl-media.com/lodging/3000000/2240000/2236200/2236109/ce67b136.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bridge Farmhouse

[](https://www.expedia.ca/Salisbury-Hotels-Bridge-Farmhouse.h2236109.Hotel-Information)

Salisbury

9.2/10

Wonderful

(19 reviews)

"Staying here felt like you walked into a story book; beautiful gardens, bridge over the creek with swans swimming up and down, sheep in the fields, views of Salisbury Cathedral, stylish decorated rooms. We greatly enjoyed our stay. "

![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg)

Jennifer E

CA $2,876

CA $3,452 total

includes taxes & fees

Jan 30 - Jan 31

[](https://www.expedia.ca/Salisbury-Hotels-Bridge-Farmhouse.h2236109.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/96000000/95300000/95290300/95290240/fe38b59b.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/96000000/95300000/95290300/95290240/9c74950f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, electric kettle](https://images.trvl-media.com/lodging/96000000/95300000/95290300/95290240/3f6b68ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/96000000/95300000/95290300/95290240/18c4e3a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bell Cottage

[](https://www.expedia.ca/Cowes-Hotels-Bell-Cottage.h95290240.Hotel-Information)

Cowes

10/10

Exceptional

(8 reviews)

"Anonymous: Accommodation lovely. Owners seem to have thought of everything to make our stay very pleasant. Nicely situated to explore the Island. Enjoyed our stay."

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

Anonymous traveller

CA $6,016

CA $6,702 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Cowes-Hotels-Bell-Cottage.h95290240.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/40000000/39440000/39439300/39439208/e37e129f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/40000000/39440000/39439300/39439208/9477e879.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/40000000/39440000/39439300/39439208/d0fa93c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![7 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/40000000/39440000/39439300/39439208/e006066e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Bury Villa - sleeping 18 guests

[](https://www.expedia.ca/Gosport-Hotels-Bury-Villa-Sleeping-18-Guests.h39439208.Hotel-Information)

Gosport

9.6/10

Exceptional

(18 reviews)

"Property was exactly how it was listed. Great location, short walk to the ferry to get over to Portsmouth & short drive to the closest beach. "

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

Zoe C.

CA $2,055

CA $2,055 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Gosport-Hotels-Bury-Villa-Sleeping-18-Guests.h39439208.Hotel-Information)

![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)

![Bar (on property)](https://images.trvl-media.com/lodging/23000000/22610000/22608700/22608660/50fcb967.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lounge](https://images.trvl-media.com/lodging/23000000/22610000/22608700/22608660/1ed0110d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### room2 Southampton Hometel

[](https://www.expedia.ca/Southampton-Hotels-Room2-Southampton.h22608660.Hotel-Information)

Southampton City Centre

9.4/10

Exceptional

(1,188 reviews)

"Staff were very helpful. Room is very well maintained and it's a warm feeling through out. "

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

Trevor Charles

CA $111

CA $133 total

includes taxes & fees

Feb 1 - Feb 2

[](https://www.expedia.ca/Southampton-Hotels-Room2-Southampton.h22608660.Hotel-Information)

![Marina](https://images.trvl-media.com/lodging/35000000/34050000/34044400/34044373/efd4c83c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/35000000/34050000/34044400/34044373/c7f569a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/35000000/34050000/34044400/34044373/72bc9396.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/35000000/34050000/34044400/34044373/39914bbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Dairy House - a house that sleeps 16 guests in 7 bedrooms

[](https://www.expedia.ca/Gosport-Hotels-Dairy-House-A-House-That-Sleeps-16-Guests-In-7-Bedrooms.h34044373.Hotel-Information)

Gosport

9.8/10

Exceptional

(30 reviews)

"Lovely well eqipped accommodation which was ideal for our family of 14\. Rooms were spacious and there was lots to do including a games room. Good location right near the sea."

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

Diane S.

CA $2,253

CA $2,253 total

includes taxes & fees

Jan 27 - Jan 28

[](https://www.expedia.ca/Gosport-Hotels-Dairy-House-A-House-That-Sleeps-16-Guests-In-7-Bedrooms.h34044373.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/69000000/68120000/68116100/68116023/f05e405f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/69000000/68120000/68116100/68116023/3a366403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/69000000/68120000/68116100/68116023/78d7e686.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/69000000/68120000/68116100/68116023/587e254b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Grove Lodge - a house that sleeps 13 guests in 5 bedrooms

[](https://www.expedia.ca/Gosport-Hotels-Grove-Lodge-A-House-That-Sleeps-13-Guests-In-5-Bedrooms.h68116023.Hotel-Information)

Gosport

9.6/10

Exceptional

(15 reviews)

"No complaints - everything was very wel organised, clean and nice. Would recommend!"

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

Johan B.

CA $1,892

CA $1,892 total

includes taxes & fees

Jan 28 - Jan 29

[](https://www.expedia.ca/Gosport-Hotels-Grove-Lodge-A-House-That-Sleeps-13-Guests-In-5-Bedrooms.h68116023.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

Aparthotels

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Apartments

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Cottages

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Private vacation homes

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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=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=CABIN)

Chalets

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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=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&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=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=CONDO)

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=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=RESIDENCE)

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=2026-04-26&d1=2026-04-26&endDate=2026-04-29&d2=2026-04-29&lodging=HOUSE_BOAT)

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## Top Winchester Hotel Reviews

![The Winchester Hotel & Spa](https://images.trvl-media.com/lodging/1000000/30000/26100/26080/4127003a_y.jpg)

### The Winchester Hotel & Spa

10/10 Excellent

"All staff very friendly & helpful. Had a great overnight stay"

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

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

### Leonardo Hotel Southampton 

10/10 Excellent

"The front desk attendant was excellent. After a long flight and commute, she was able to expedite the process of getting us checked in. This was exceptional professionalism. "

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

![The Langstone Quays](https://images.trvl-media.com/lodging/1000000/10000/8600/8541/952fcd26_y.jpg)

### The Langstone Quays

10/10 Excellent

"Nice rooms, staff and beds "

[](https://expedia.ca/Hayling-Island-Hotels-The-Langstone-Quays.h8541.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

"Very clean, lovely staff & delicious food!"

[](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

"T"

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

"Breakfast was amazing"

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

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

### Royal Maritime Hotel

10/10 Excellent

"Great stay"

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

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

### Harbour Hotel Southampton

10/10 Excellent

"Very nice place with restaurants and bars, spa and 5 stars service. "

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

"Wonderful staff, lovely room and amenities. Missed a chance to enjoy the spa as didn’t realise early enough to book in advance - just means we have to come back! Food also very good 😊 "

[](https://expedia.ca/Winchester-Hotels-Holiday-Inn-Winchester.h3430824.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.   

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- [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

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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)

Cars

- [Car rentals in Gatwick](https://expedia.ca/Car-Rentals-In-Gatwick.d182523.Car-Rental-Guide)

Activities

- [Things to do in Sudbury](https://expedia.ca/Things-To-Do-In-Sudbury.d5705.Travel-Guide-Activities)
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General

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