Title: Winson Vacation Rentals from CA $138: Short-Term Rentals for 2026 | Expedia.ca

[Winson Travel Guide](https://expedia.ca/Winson.dx3000716482)[Hotels in Winson](https://expedia.ca/Winson-Hotels.d3000716482.Travel-Guide-Hotels)[Winson Car Rentals](https://expedia.ca/Car-Rentals-In-Winson.d3000716482.Car-Rental-Guide)[Winson Vacation Packages](https://expedia.ca/Winson.d3000716482.Destination-Travel-Guides)

![St Michael's Cottage, Winson. This small cottage is situated in the corner of the churchyard.](https://images.trvl-media.com/place/3000716482/2b589edb-395c-442f-9049-0f67aa18a601.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Philip Halling

![](https://images.trvl-media.com/place/3000716482/2b589edb-395c-442f-9049-0f67aa18a601.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

- ![](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

In two weeks

[Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=3000716482&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 two months

[Apr 24 - Apr 26](https://www.expedia.ca/Hotel-Search?regionId=3000716482&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 three months

[May 22 - May 24](https://www.expedia.ca/Hotel-Search?regionId=3000716482&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 four months

[Jun 19 - Jun 21](https://www.expedia.ca/Hotel-Search?regionId=3000716482&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)

## Our top choices for Winson vacation rentals

![Property grounds](https://images.trvl-media.com/lodging/99000000/98290000/98286700/98286623/eac802ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/99000000/98290000/98286700/98286623/1adee4b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, electric kettle, toaster, cookware/dishes/utensils](https://images.trvl-media.com/lodging/99000000/98290000/98286700/98286623/415c2616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, individually decorated, individually furnished, free WiFi](https://images.trvl-media.com/lodging/99000000/98290000/98286700/98286623/f55fd92c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Burford

[](https://www.expedia.ca/Burford-Hotels-The-Rookery.h98286623.Hotel-Information)

CA $556

CA $668 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Burford-Hotels-The-Rookery.h98286623.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/108000000/107910000/107903800/107903796/37da9bea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Patio, City View | Private kitchen](https://images.trvl-media.com/lodging/108000000/107910000/107903800/107903796/3cdbc572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Patio, City View](https://images.trvl-media.com/lodging/108000000/107910000/107903800/107903796/0b0aa4a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Patio, City View | Private kitchen](https://images.trvl-media.com/lodging/108000000/107910000/107903800/107903796/fecab649.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Chipping Norton

[](https://www.expedia.ca/Chipping-Norton-Hotels-Cosy-2BD-Cottage-Near-Daylesford.h107903796.Hotel-Information)

CA $207

CA $432 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Chipping-Norton-Hotels-Cosy-2BD-Cottage-Near-Daylesford.h107903796.Hotel-Information)

![Classic Double Room, Non Smoking](https://images.trvl-media.com/lodging/113000000/112750000/112749800/112749800/e246fcee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/113000000/112750000/112749800/112749800/8020bddf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Room, 2 Double Beds, Non Smoking | Private kitchen](https://images.trvl-media.com/lodging/113000000/112750000/112749800/112749800/5dd104c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/113000000/112750000/112749800/112749800/317a74f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Broadway

[](https://www.expedia.ca/Broadway-Hotels-George-Apartments.h112749800.Hotel-Information)

9.6/10

Exceptional

(20 reviews)

"Spotlessly clean, super location and the parking space was a godsend with how busy Broadway is during New Year. Having stayed in the village for the past 15 years this was one of the best properties that I have stayed in. "

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

Keelan

CA $174

CA $209 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Broadway-Hotels-George-Apartments.h112749800.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/113000000/112690000/112682900/112682849/5802a2a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/113000000/112690000/112682900/112682849/53b47bbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/113000000/112690000/112682900/112682849/aa9dde64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/113000000/112690000/112682900/112682849/6d801ca7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Malmesbury

[](https://www.expedia.ca/Malmesbury-Hotels-Eilmers-Cottage-Lovely-4BD-In-Malmesbury.h112682849.Hotel-Information)

[](https://www.expedia.ca/Malmesbury-Hotels-Eilmers-Cottage-Lovely-4BD-In-Malmesbury.h112682849.Hotel-Information)

![In-room dining](https://images.trvl-media.com/lodging/125000000/124250000/124241500/124241452/f5f2dfa0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/125000000/124250000/124241500/124241452/cefa8087.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/125000000/124250000/124241500/124241452/7f9f3542.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room dining](https://images.trvl-media.com/lodging/125000000/124250000/124241500/124241452/58c8e61e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Bourton-on-the-Water

[](https://www.expedia.ca/Cheltenham-Hotels-Stunning-2BD-In-Bourton-On-The-Water.h124241452.Hotel-Information)

CA $274

CA $539 total

includes taxes & fees

Mar 19 - Mar 20

[](https://www.expedia.ca/Cheltenham-Hotels-Stunning-2BD-In-Bourton-On-The-Water.h124241452.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/126000000/125160000/125158500/125158444/36268759.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/126000000/125160000/125158500/125158444/2ba18d60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/126000000/125160000/125158500/125158444/e7eb63ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/126000000/125160000/125158500/125158444/ba69d638.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Burford

[](https://www.expedia.ca/Burford-Hotels-Stunning-2-Bedroom-Cottage-Near-Burford.h125158444.Hotel-Information)

CA $282

CA $743 total

includes taxes & fees

Mar 15 - Mar 16

[](https://www.expedia.ca/Burford-Hotels-Stunning-2-Bedroom-Cottage-Near-Burford.h125158444.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/109000000/108570000/108560900/108560819/b1fee42e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/109000000/108570000/108560900/108560819/410896ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | Private kitchen](https://images.trvl-media.com/lodging/109000000/108570000/108560900/108560819/7c0a28b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House | Interior](https://images.trvl-media.com/lodging/109000000/108570000/108560900/108560819/890b8cc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Chipping Norton

[](https://www.expedia.ca/Chipping-Norton-Hotels-Windsor-Cottage-Bolthole-In-Heart-Of-CN.h108560819.Hotel-Information)

10/10

Exceptional

(2 reviews)

"Had a lovely stay at Windsor cottage. Well presented, great amenities and the most comfortable bed in the master bedroom. Slept like a log! Ate out in local restaurants, which were lovely especially Alberto’s Italy. There are a couple of free parking areas in town 5-10 minutes away. During our stay there was a film set in place for Father Brown and a restriction at the end of the road. It didn’t take away from our stay, but was glad of the premier inn parking just a 100m away. We pulled up to...

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

Anonymous traveller

CA $187

CA $409 total

includes taxes & fees

Mar 25 - Mar 26

[](https://www.expedia.ca/Chipping-Norton-Hotels-Windsor-Cottage-Bolthole-In-Heart-Of-CN.h108560819.Hotel-Information)

![Family Cottage, Private Bathroom | Interior](https://images.trvl-media.com/lodging/68000000/67270000/67269800/67269735/334d592d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Garden](https://images.trvl-media.com/lodging/68000000/67270000/67269800/67269735/18647f99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Cottage, Private Bathroom | Exterior](https://images.trvl-media.com/lodging/68000000/67270000/67269800/67269735/c3332657.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Cottage, Private Bathroom | Lounge](https://images.trvl-media.com/lodging/68000000/67270000/67269800/67269735/1f000228.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Cheltenham

[](https://www.expedia.ca/Cheltenham-Hotels-Cotswold-Cottage-Gems-Oakey-Cottage.h67269735.Hotel-Information)

10/10

Exceptional

(1 review)

"Beautiful location on the outskirts of Bourton on the Water. Within easy walking distance of the centre. Totally dog friendly. Excellent and plentiful provisions for breakfast. Everything you would want when away. Definitely would go again."

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

Anita

CA $437

CA $524 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Cheltenham-Hotels-Cotswold-Cottage-Gems-Oakey-Cottage.h67269735.Hotel-Information)

![50-inch Smart TV with cable channels, TV, Netflix](https://images.trvl-media.com/lodging/75000000/74640000/74638400/74638352/996838d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/75000000/74640000/74638400/74638352/2c487a96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Egyptian cotton sheets, premium bedding, individually decorated](https://images.trvl-media.com/lodging/75000000/74640000/74638400/74638352/d46cd11d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74640000/74638400/74638352/2fe5b1d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in South Swindon

[](https://www.expedia.ca/Swindon-Hotels-Suite-Life-Serviced-Apartments.h74638352.Hotel-Information)

8.4/10

Very good

(24 reviews)

"Always love my stays at these apartments! Feels so homely, easy location for my work and very spacious. Spotlessly clean every time & private parking right outside."

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

Sophie

[](https://www.expedia.ca/Swindon-Hotels-Suite-Life-Serviced-Apartments.h74638352.Hotel-Information)

![In-room dining](https://images.trvl-media.com/lodging/118000000/117020000/117012200/117012194/ab5d0770_edited_1351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/118000000/117020000/117012200/117012194/10b933eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![In-room dining](https://images.trvl-media.com/lodging/118000000/117020000/117012200/117012194/3f260173.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/118000000/117020000/117012200/117012194/bb031f25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Chipping Norton

[](https://www.expedia.ca/Chipping-Norton-Hotels-Field-House-Stunning-3BD-Home-In-Kingham.h117012194.Hotel-Information)

CA $584

CA $996 total

includes taxes & fees

Mar 11 - Mar 12

[](https://www.expedia.ca/Chipping-Norton-Hotels-Field-House-Stunning-3BD-Home-In-Kingham.h117012194.Hotel-Information)

![Balcony](https://images.trvl-media.com/lodging/84000000/83560000/83559200/83559172/e12076d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, dishwasher, electric kettle, toaster](https://images.trvl-media.com/lodging/84000000/83560000/83559200/83559172/4ce6146a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/84000000/83560000/83559200/83559172/fa4eaf10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83560000/83559200/83559172/b19fdf55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Stonehouse

[](https://www.expedia.ca/Stonehouse-Hotels-Tinkley-Cottage.h83559172.Hotel-Information)

CA $823

CA $988 total

includes taxes & fees

Mar 4 - Mar 5

[](https://www.expedia.ca/Stonehouse-Hotels-Tinkley-Cottage.h83559172.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108090000/108080200/108080166/10e50095.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, Garden View | Living area](https://images.trvl-media.com/lodging/109000000/108090000/108080200/108080166/d1b4c190.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/109000000/108090000/108080200/108080166/2edb00b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/109000000/108090000/108080200/108080166/6941b3ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cheltenham

[](https://www.expedia.ca/Cheltenham-Hotels-Jasmine-Cottage-2BD-In-Heart-Of-Bourton.h108080166.Hotel-Information)

10/10

Exceptional

(3 reviews)

"Very thoughtfully prepared cozy space. We enjoyed staying there with our two daughters. The o communication was excellent and check in and out very seamless. Location is superb if desiring to stay in Burton in the water. Beautiful, quaint town. Only complaint was lack of cooling. Luckily able to cool off at night with windows open. We really enjoyed our stay. "

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

Ryan

CA $243

CA $494 total

includes taxes & fees

Mar 5 - Mar 6

[](https://www.expedia.ca/Cheltenham-Hotels-Jasmine-Cottage-2BD-In-Heart-Of-Bourton.h108080166.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/109000000/108590000/108586800/108586745/06d8c7e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108590000/108586800/108586745/843b7c68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 2 Bedrooms, Garden View | Living area](https://images.trvl-media.com/lodging/109000000/108590000/108586800/108586745/a11afc1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 2 Bedrooms, Garden View](https://images.trvl-media.com/lodging/109000000/108590000/108586800/108586745/1012cd51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Chipping Norton

[](https://www.expedia.ca/Chipping-Norton-Hotels-Maple-Cottage-Beautiful-2BD-Retreat.h108586745.Hotel-Information)

10/10

Exceptional

(3 reviews)

"It was the perfect stay during the festive season! Super cosy by the fire. Host was lovely and easy to communicate with. Highly recommend."

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

Libby

CA $250

CA $704 total

includes taxes & fees

Mar 12 - Mar 13

[](https://www.expedia.ca/Chipping-Norton-Hotels-Maple-Cottage-Beautiful-2BD-Retreat.h108586745.Hotel-Information)

![Front of property](https://images.trvl-media.com/lodging/115000000/114590000/114588000/114587945/ab6149ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cottage, Garden View](https://images.trvl-media.com/lodging/115000000/114590000/114588000/114587945/w717h480x0y0-e46a261b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/115000000/114590000/114588000/114587945/3b3c8328.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/115000000/114590000/114588000/114587945/7fd19644.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Farmington

[](https://www.expedia.ca/Cheltenham-Hotels-Country-Cottage-In-Heart-Of-The-Cotswold.h114587945.Hotel-Information)

6.0/10

(1 review)

"Lovely place in a peaceful and quiet location, however I did not recieve any check in instructions and was a bit disappointed that there was no tea/coffee at all in such a remote location. "

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

Stephanie

CA $262

CA $498 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Cheltenham-Hotels-Country-Cottage-In-Heart-Of-The-Cotswold.h114587945.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/102000000/101470000/101460100/101460037/f5d7e4fe_edited_eca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Double Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/102000000/101470000/101460100/101460037/61ca0d89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Double Room, 1 Bedroom, Non Smoking](https://images.trvl-media.com/lodging/102000000/101470000/101460100/101460037/5c81b731.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Superior Double Room, 1 Bedroom, Non Smoking](https://images.trvl-media.com/lodging/102000000/101470000/101460100/101460037/8a5210d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Aparthotel in Cheltenham

[](https://www.expedia.ca/Cheltenham-Hotels-Crescent-Place.h101460037.Hotel-Information)

9.4/10

Exceptional

(98 reviews)

"Room spotless great location helpful staff great parking facility "

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

Joanne

CA $130

CA $157 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Cheltenham-Hotels-Crescent-Place.h101460037.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/109000000/108330000/108320900/108320858/95dc4883.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/109000000/108330000/108320900/108320858/7d0cd337.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/109000000/108330000/108320900/108320858/ba9a9fef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/109000000/108330000/108320900/108320858/b8904eba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Upper Oddington

[](https://www.expedia.ca/Moreton-In-Marsh-Hotels-Crooked-Cottage-In-Picturesque-Upper-Oddington-Pass-The-Keys.h108320858.Hotel-Information)

CA $303

CA $395 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Moreton-In-Marsh-Hotels-Crooked-Cottage-In-Picturesque-Upper-Oddington-Pass-The-Keys.h108320858.Hotel-Information)

![Apartment](https://images.trvl-media.com/lodging/90000000/89560000/89556000/89555924/e6b0cdae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/90000000/89560000/89556000/89555924/01e53d45.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89560000/89556000/89555924/552f8d39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment | Private kitchen](https://images.trvl-media.com/lodging/90000000/89560000/89556000/89555924/a0f31046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Gloucester

[](https://www.expedia.ca/Gloucester-Hotels-Stylish-Loft-Style-Two-Bedroom-Apartment.h89555924.Hotel-Information)

10/10

Exceptional

(1 review)

"Great flat local to Gloucester and the docks. Sometimes the out of hours contact was hard to get hold of but that is no way a negative on the flat. Very tidy and clean with all basic items you need."

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

Wayne

CA $307

CA $368 total

includes taxes & fees

Mar 9 - Mar 10

[](https://www.expedia.ca/Gloucester-Hotels-Stylish-Loft-Style-Two-Bedroom-Apartment.h89555924.Hotel-Information)

![Studio, Ensuite (Stable) | Lounge](https://images.trvl-media.com/lodging/71000000/70960000/70954800/70954789/679d352a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/71000000/70960000/70954800/70954789/57304469.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/71000000/70960000/70954800/70954789/0558aa6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Apartment, Ensuite (Coach House) | Lounge](https://images.trvl-media.com/lodging/71000000/70960000/70954800/70954789/418db649.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Stroud

[](https://www.expedia.ca/Stroud-Hotels-The-Coach-House-And-The-Stable.h70954789.Hotel-Information)

9.0/10

Wonderful

(41 reviews)

"Really lovely accommodation. Staff were very friendly and helpful and made sure check in and out was easy. We went to the pub for food and it was excellent - great menu and well cooked and presented. Staff were really helpful again Lovely area for a walk or trip to the vineyard "

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

Helen

CA $115

CA $138 total

includes taxes & fees

Mar 8 - Mar 9

[](https://www.expedia.ca/Stroud-Hotels-The-Coach-House-And-The-Stable.h70954789.Hotel-Information)

![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/84000000/83410000/83401000/83400916/dbdac64c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/84000000/83410000/83401000/83400916/b7a22744.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83410000/83401000/83400916/69e998b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/84000000/83410000/83401000/83400916/142296ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Malmesbury

[](https://www.expedia.ca/Malmesbury-Hotels-Old-England-Cottage.h83400916.Hotel-Information)

9.8/10

Exceptional

(9 reviews)

"Great overall stay."

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

james c.

CA $255

CA $448 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Malmesbury-Hotels-Old-England-Cottage.h83400916.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/33000000/32940000/32932900/32932805/76aae0b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/33000000/32940000/32932900/32932805/2b6fc787.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace, Netflix, streaming services](https://images.trvl-media.com/lodging/33000000/32940000/32932900/32932805/0ae19939.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi, bed sheets](https://images.trvl-media.com/lodging/33000000/32940000/32932900/32932805/b836fea4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Chedworth, near Cheltenham

[](https://www.expedia.ca/Cheltenham-Hotels-1-Bedroom-Accommodation-In-Chedworth.h32932805.Hotel-Information)

9.8/10

Exceptional

(20 reviews)

"Ivy Cottage was definitely one of the nicest cottages I have ever stayed in. It was clean, cosy, warm, spacious, well-equipped and very comfortable. And the village is lovely too."

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

Fiona P.

CA $579

CA $579 total

includes taxes & fees

Mar 2 - Mar 3

[](https://www.expedia.ca/Cheltenham-Hotels-1-Bedroom-Accommodation-In-Chedworth.h32932805.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=2026-03-15&endDate=2026-03-16&regionId=3000716482&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=VR_SPRING_PROMO_3000716482)

## Find vacation rentals that suit your style

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Winson%2C+Cirencester%2C+England%2C+United+Kingdom&regionId=3000716482&latLong=51.7667%2C-1.8667&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Winson%2C+Cirencester%2C+England%2C+United+Kingdom&regionId=3000716482&latLong=51.7667%2C-1.8667&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=APARTMENT)

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Winson%2C+Cirencester%2C+England%2C+United+Kingdom&regionId=3000716482&latLong=51.7667%2C-1.8667&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=CABIN)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Winson%2C+Cirencester%2C+England%2C+United+Kingdom&regionId=3000716482&latLong=51.7667%2C-1.8667&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=VILLA)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Winson%2C+Cirencester%2C+England%2C+United+Kingdom&regionId=3000716482&latLong=51.7667%2C-1.8667&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=COTTAGE)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Winson%2C+Cirencester%2C+England%2C+United+Kingdom&regionId=3000716482&latLong=51.7667%2C-1.8667&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=CONDO)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Winson%2C+Cirencester%2C+England%2C+United+Kingdom&regionId=3000716482&latLong=51.7667%2C-1.8667&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=VACATION_HOME)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Winson%2C+Cirencester%2C+England%2C+United+Kingdom&regionId=3000716482&latLong=51.7667%2C-1.8667&adults=2&startDate=2026-05-29&d1=2026-05-29&endDate=2026-06-01&d2=2026-06-01&lodging=CHALET)

![](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%2FWinson-Vacation-Rentals.d3000716482.Travel-Guide-VacationRentals)[

Sign up, it's free

](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinson-Vacation-Rentals.d3000716482.Travel-Guide-VacationRentals)

## Top Winson Hotel Reviews

![The Slaughters Country Inn](https://images.trvl-media.com/lodging/6000000/5490000/5484300/5484211/cddd380a_y.jpg)

### The Slaughters Country Inn

10/10 Excellent

"The hotel is in a wonderful location. Our room was clean, generally well e"

[](https://expedia.ca/Cheltenham-Hotels-The-Slaughters-Country-Inn.h5484211.Hotel-Information)

![Holiday Inn Express Cheltenham by IHG](https://images.trvl-media.com/lodging/2000000/1950000/1942000/1941979/d0da9d2c_y.jpg)

### Holiday Inn Express Cheltenham by IHG

10/10 Excellent

"Great location, friendly staff"

[](https://expedia.ca/Cheltenham-Hotels-Holiday-Inn-Express-Cheltenham.h1941979.Hotel-Information)

![Mollie's Motel and Diner](https://images.trvl-media.com/lodging/34000000/33340000/33335900/33335815/794550ca_y.jpg)

### Mollie's Motel and Diner

10/10 Excellent

"The room was great and cosy but what stood out most was the immense, incredible and unique service from the hosts - especially Daryl, who catered to me in desperate times of need. I was there with my production team, as we were shooting for a TV Advert and Daryl went out of her way to make sure we were accommodated and had everything we needed and more in abundance. We had an emergency situation with our kit, which was my error, but Daryl went out of her way to deal with the situation with a last minute contingency - she then helped me print out documents that I needed, which again I should've had sorted myself whilst also maintaining hospitable qualities through offering me drinks and checking I was okay. I couldn't have possibly asked for more. I know exactly where I would recommend myself and others if we were in the area. I would like to thank Daryl very much - what a absolute gem of a person."

[](https://expedia.ca/Faringdon-Hotels-Mollies-Motel.h33335815.Hotel-Information)

![The Royal George Birdlip by Greene King Inns](https://images.trvl-media.com/lodging/3000000/2560000/2557300/2557286/786fb323_y.jpg)

### The Royal George Birdlip by Greene King Inns

10/10 Excellent

"Perfect x"

[](https://expedia.ca/Gloucester-Hotels-The-Royal-George-Birdlip-By-Greene-King-Inns.h2557286.Hotel-Information)

![Stratton House Hotel & Spa](https://images.trvl-media.com/lodging/1000000/30000/28500/28411/57e9cd87_y.jpg)

### Stratton House Hotel & Spa

10/10 Excellent

"Friendly staff. Great food and fantastic spa and treatments. "

[](https://expedia.ca/Cirencester-Hotels-Stratton-House-Hotel-Spa.h28411.Hotel-Information)

![Queens Hotel Cheltenham](https://images.trvl-media.com/lodging/1000000/180000/175700/175669/48f6acd1_y.jpg)

### Queens Hotel Cheltenham

10/10 Excellent

"The bed was so comfy and the staff were lovely :)"

[](https://expedia.ca/Cheltenham-Hotels-Queens-Hotel-Cheltenham-MGallery.h175669.Hotel-Information)

![Delta Hotels by Marriott Swindon](https://images.trvl-media.com/lodging/1000000/30000/23300/23229/08e5e2f1_y.jpg)

### Delta Hotels by Marriott Swindon

10/10 Excellent

"Very nice and very friendly staff "

[](https://expedia.ca/Swindon-Hotels-Swindon-Marriott-Hotel.h23229.Hotel-Information)

![Leonardo Hotel Swindon ](https://images.trvl-media.com/lodging/3000000/2640000/2631500/2631422/a5c86301_y.jpg)

### Leonardo Hotel Swindon 

10/10 Excellent

"Very clean and convenient for town centre and railway station."

[](https://expedia.ca/Swindon-Hotels-Jurys-Inn-Swindon.h2631422.Hotel-Information)

![Hatherley Manor Hotel & Spa](https://images.trvl-media.com/lodging/17000000/16240000/16238300/16238215/0a381be4_y.jpg)

### Hatherley Manor Hotel & Spa

10/10 Excellent

"Room was very good and the spa was amazing Lovely place "

[](https://expedia.ca/Gloucester-Hotels-Hatherley-Manor-Hotel-Spa.h16238215.Hotel-Information)

## Find out more about Winson

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 Winson. 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

### 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)

## Frequently asked questions

### Can I find a vacation rental in Winson?

### What are some of the best vacation home rentals that Winson has to offer?

### What’s there to see and do in Winson?

### What’s a vacation rental in Winson like?

![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg)

## Go further with the Expedia app

Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go.

Scan the QR code with your device camera and download our app