Title: Windsor and Maidenhead Vacation Rentals from CA $227: Short-Term Rentals for 2026 | Expedia.ca

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![Where will you be on 19 May 2018?

In Windsor Castle, attending the wedding of Prince Harry and Meghan Markle?

Or maybe in Wembley watching the FA Cup final?](https://images.trvl-media.com/place/5479/82313c0b-4a04-4809-bef7-46b3b43c3451.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

Photo by Olivier Aurand

![](https://images.trvl-media.com/place/5479/82313c0b-4a04-4809-bef7-46b3b43c3451.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Our top choices for Windsor and Maidenhead vacation rentals

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/47000000/46070000/46066900/46066853/2eb22f89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/47000000/46070000/46066900/46066853/71d2419b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/47000000/46070000/46066900/46066853/41d431d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/47000000/46070000/46066900/46066853/ee139021.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious, light apartment sleeps up to four

[](https://www.expedia.ca/Maidenhead-Hotels-Vrbo-Property.h46066853.Hotel-Information)

Cookham

9.8/10

Exceptional

(18 reviews)

"Beautifully refurbished property with very helpful hosts."

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

Alexandra C.

CA $183

CA $384 total

includes taxes & fees

Feb 14 - Feb 15

[](https://www.expedia.ca/Maidenhead-Hotels-Vrbo-Property.h46066853.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/113000000/112880000/112873300/112873262/f29c4171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/113000000/112880000/112873300/112873262/d36daf42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112880000/112873300/112873262/3dff802d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/113000000/112880000/112873300/112873262/dd2bc9fb_edited_ef9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.

[](https://www.expedia.ca/Windsor-Hotels-A-Cosy-Cabin-Retreat-5-Mins-Away-From-Windsor-And-10-Mins-From-Legoland.h112873262.Hotel-Information)

Old Windsor

9.6/10

Exceptional

(4 reviews)

"Had a great stay prior to our flight home. They had everything we needed including things for the kids (1 and 3)."

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

Peyton T.

CA $208

CA $237 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Windsor-Hotels-A-Cosy-Cabin-Retreat-5-Mins-Away-From-Windsor-And-10-Mins-From-Legoland.h112873262.Hotel-Information)

![Property entrance](https://images.trvl-media.com/lodging/19000000/18690000/18689500/18689487/41e4f9af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio, 1 Bedroom, Garden View, Ground Floor (Garden Lodge)](https://images.trvl-media.com/lodging/19000000/18690000/18689500/18689487/27ca1557.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio, 1 Bedroom, Garden View, Ground Floor (Garden Lodge)](https://images.trvl-media.com/lodging/19000000/18690000/18689500/18689487/04e496cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Studio, 1 Bedroom, Garden View, Ground Floor (Garden Lodge)](https://images.trvl-media.com/lodging/19000000/18690000/18689500/18689487/aaaca882.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Willow Court Farm

[](https://www.expedia.ca/Windsor-Hotels-Willow-Court-Farm.h18689487.Hotel-Information)

Windsor

10/10

Exceptional

(200 reviews)

"Wonderful place ideal for families "

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

Zoe

CA $189

CA $227 total

includes taxes & fees

Feb 13 - Feb 14

[](https://www.expedia.ca/Windsor-Hotels-Willow-Court-Farm.h18689487.Hotel-Information)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/89000000/88290000/88285100/88285073/40a55b11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/89000000/88290000/88285100/88285073/8a38f635.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/89000000/88290000/88285100/88285073/b00fab4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/89000000/88290000/88285100/88285073/d351ed3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stay In Style With Castle Views/Prime Spot Windsor

[](https://www.expedia.ca/Windsor-Hotels-Stay-In-Style-With-Castle-ViewsPrime-Spot-Windsor.h88285073.Hotel-Information)

Windsor City Centre

10/10

Exceptional

(2 reviews)

"This place was perfect for us. It’s exactly as listed on the site, super cute and very comfortable plus there really is a view of the castle! We had a couple small things we needed help with and the host management company was very helpful and responsive. There’s a cut through to the long walk just up the street and you can be in the center of town in 10 min or less. Would stay again!"

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

Amy R.

CA $205

CA $328 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Windsor-Hotels-Stay-In-Style-With-Castle-ViewsPrime-Spot-Windsor.h88285073.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/75000000/74520000/74514900/74514828/0664ee54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74520000/74514900/74514828/cf379c56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/75000000/74520000/74514900/74514828/015dda36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74520000/74514900/74514828/701d2504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relaxing guest house with Jacuzzi & boat hire

[](https://www.expedia.ca/Staines-Hotels-River-Guest-House-With-Jacuzzi.h74514828.Hotel-Information)

Wraysbury

10/10

Exceptional

(17 reviews)

"Cabin very clean and tidy lovely location very pleasant owner would definitely recommend to others and i would definitely stay again"

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

Wayne M.

CA $422

CA $469 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Staines-Hotels-River-Guest-House-With-Jacuzzi.h74514828.Hotel-Information)

![Comfort Apartment, 2 Bedrooms, Non Smoking](https://images.trvl-media.com/lodging/31000000/30240000/30237500/30237492/c6871ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Apartment, 2 Bedrooms, Non Smoking | Private kitchen](https://images.trvl-media.com/lodging/31000000/30240000/30237500/30237492/5a0e0ca7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/31000000/30240000/30237500/30237492/c0f98b64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Comfort Apartment, 2 Bedrooms, Non Smoking](https://images.trvl-media.com/lodging/31000000/30240000/30237500/30237492/f30435d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Hampden Apartments - The George

[](https://www.expedia.ca/Windsor-Hotels-Hampden-Apartments-The-George.h30237492.Hotel-Information)

Windsor City Centre

9.0/10

Wonderful

(34 reviews)

"Super convenient for visiting everything in Windsor. Plenty of food nearby, lots of options. The property itself was a little run down, half of the shades didn’t work, most of the freezer was unusable because of ice build up, the washing machine is a combo washer dryer, but it doesn’t dry your clothes at all, you have to hang them up."

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

Timothy

CA $342

CA $342 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Windsor-Hotels-Hampden-Apartments-The-George.h30237492.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/101000000/100930000/100928100/100928058/970ad50a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/101000000/100930000/100928100/100928058/1b663f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/101000000/100930000/100928100/100928058/808efffd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, highchair](https://images.trvl-media.com/lodging/101000000/100930000/100928100/100928058/bda5af61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Doorstep Of Windsor Castle Chic: 1BR|Parking

[](https://www.expedia.ca/Windsor-Hotels-Windsor-Castle-Chic-1BRParking.h100928058.Hotel-Information)

Windsor City Centre

9.2/10

Wonderful

(5 reviews)

"Great place to stay for visiting the castle and surrounding areas with the bonus of a parking space.Place was very clean and warm with plenty of bars and restaurants minutes away. Would definitely go back."

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

Richard J.

[](https://www.expedia.ca/Windsor-Hotels-Windsor-Castle-Chic-1BRParking.h100928058.Hotel-Information)

![TV, offices](https://images.trvl-media.com/lodging/89000000/88290000/88284800/88284782/f1c0f858.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/89000000/88290000/88284800/88284782/ba8c3188.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/89000000/88290000/88284800/88284782/ba1f0dc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/89000000/88290000/88284800/88284782/e0a2577b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 BED/2 BATH & FREE PARKING! ❤ CENTRAL WINDSOR ❤

[](https://www.expedia.ca/Windsor-Hotels-2-BED2-BATH-FREE-PARKING-CENTRAL-WINDSOR.h88284782.Hotel-Information)

Windsor City Centre

10/10

Exceptional

(6 reviews)

"Great little apartment walkable to everything in Windsor - great space!"

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

Leslie C.

CA $255

CA $458 total

includes taxes & fees

Feb 17 - Feb 18

[](https://www.expedia.ca/Windsor-Hotels-2-BED2-BATH-FREE-PARKING-CENTRAL-WINDSOR.h88284782.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/102000000/101830000/101830000/101829957/14d64bfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101830000/101830000/101829957/d5a5be8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/102000000/101830000/101830000/101829957/adbe13ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/102000000/101830000/101830000/101829957/73eda705.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Character Victorian apartment close to Windsor town with secure parking

[](https://www.expedia.ca/Windsor-Hotels-Character-Victorian-Apartment-Close-To-Windsor-Town-With-Secure-Parking.h101829957.Hotel-Information)

Clewer East

10/10

Exceptional

(1 review)

"A gorgeous opulent place to stay while in Windsor. We appreciated the extra touches like the fresh milk for tea!"

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

Isabel

CA $329

CA $398 total

includes taxes & fees

Feb 18 - Feb 19

[](https://www.expedia.ca/Windsor-Hotels-Character-Victorian-Apartment-Close-To-Windsor-Town-With-Secure-Parking.h101829957.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/112000000/111940000/111939800/111939779/w1853h1244x0y0-9455e414.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/112000000/111940000/111939800/111939779/w1819h1248x0y0-04310389.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/112000000/111940000/111939800/111939779/c0765b48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/112000000/111940000/111939800/111939779/w1818h1256x0y0-c891faf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Windsor Home with Free Parking

[](https://www.expedia.ca/Windsor-Hotels-Windsor-Home-With-Free-Parking-No-Cleaning-Fees.h111939779.Hotel-Information)

Clewer South

CA $231

CA $314 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Windsor-Hotels-Windsor-Home-With-Free-Parking-No-Cleaning-Fees.h111939779.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/119000000/118920000/118917400/118917349/e14f757d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![View from property](https://images.trvl-media.com/lodging/119000000/118920000/118917400/118917349/2accab7c.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/119000000/118920000/118917400/118917349/1839a23e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Point of interest](https://images.trvl-media.com/lodging/119000000/118920000/118917400/118917349/2641dd0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Studio with Stunning Windsor Castle Views

[](https://www.expedia.ca/Windsor-Hotels-Charming-Studio-With-Stunning-Windsor-Castle-Views.h118917349.Hotel-Information)

Windsor City Centre

10/10

Exceptional

(2 reviews)

"Awesome location. Clean, comfortable room. "

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

Ephraim M.

[](https://www.expedia.ca/Windsor-Hotels-Charming-Studio-With-Stunning-Windsor-Castle-Views.h118917349.Hotel-Information)

![Cabin | Property grounds](https://images.trvl-media.com/lodging/75000000/74500000/74497600/74497512/9dd9f462.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin](https://images.trvl-media.com/lodging/75000000/74500000/74497600/74497512/29d50e4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin | Exterior](https://images.trvl-media.com/lodging/75000000/74500000/74497600/74497512/743b0cb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Cabin | Property grounds](https://images.trvl-media.com/lodging/75000000/74500000/74497600/74497512/00740680.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire

[](https://www.expedia.ca/Egham-Hotels-River-Guest-House-Retreat-With-Jacuzzi-Hire.h74497512.Hotel-Information)

Wraysbury

10/10

Exceptional

(1 review)

CA $353

CA $479 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Egham-Hotels-River-Guest-House-Retreat-With-Jacuzzi-Hire.h74497512.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/118000000/117960000/117952300/117952238/a7254008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/118000000/117960000/117952300/117952238/21220e78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer](https://images.trvl-media.com/lodging/118000000/117960000/117952300/117952238/5fe98225.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Television](https://images.trvl-media.com/lodging/118000000/117960000/117952300/117952238/d9e3e786.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### SnoozeDen Westmead| Double Room

[](https://www.expedia.ca/Windsor-Hotels-SnoozeDen-Westmead-Double-Room.h117952238.Hotel-Information)

Clewer East

CA $114

CA $114 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Windsor-Hotels-SnoozeDen-Westmead-Double-Room.h117952238.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/96000000/95030000/95026100/95026004/80cf2439.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/96000000/95030000/95026100/95026004/1749a8ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/96000000/95030000/95026100/95026004/34ddb5d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95030000/95026100/95026004/d82a7a36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 3Bed 3Bath Home in Windsor with parking!

[](https://www.expedia.ca/Windsor-Hotels-Charming-3Bed-3Bath-Home-In-Windsor-With-Parking.h95026004.Hotel-Information)

Windsor City Centre

10/10

Exceptional

(2 reviews)

"The apartment look like it had just been remodeled, and it was furnished very nicely. Everything was in working order. It was walking distance from Windsor Center and the castle. There were three couples, and we each enjoyed having our own bedroom and bathroom combo"

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

Elizabeth l.

CA $320

CA $591 total

includes taxes & fees

Feb 16 - Feb 17

[](https://www.expedia.ca/Windsor-Hotels-Charming-3Bed-3Bath-Home-In-Windsor-With-Parking.h95026004.Hotel-Information)

![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/104000000/103330000/103327500/103327451/b8eb816d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, hair dryer, towels](https://images.trvl-media.com/lodging/104000000/103330000/103327500/103327451/0c256f1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/104000000/103330000/103327500/103327451/4bd6f5ab_edited_27be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, dishwasher, toaster](https://images.trvl-media.com/lodging/104000000/103330000/103327500/103327451/19f040c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious Apartment with Private Garden

[](https://www.expedia.ca/Windsor-Hotels-Spacious-Apartment-With-Private-Garden.h103327451.Hotel-Information)

Windsor City Centre

8.0/10

Very good

(3 reviews)

"I traveled to Windsor with my husband and 17 year old daughter. This apartment has a good layout with two separate bedrooms and is within walking distance of train station, shops, restaurants and the castle. We had a great stay."

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

Sherry N.

CA $166

CA $346 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Windsor-Hotels-Spacious-Apartment-With-Private-Garden.h103327451.Hotel-Information)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/98000000/97360000/97353500/97353427/1cd17435.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/98000000/97360000/97353500/97353427/6fb72c46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/98000000/97360000/97353500/97353427/4d022b48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, toaster](https://images.trvl-media.com/lodging/98000000/97360000/97353500/97353427/36b61a76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Shepherds Hut with Hot Tub Retreat

[](https://www.expedia.ca/Maidenhead-Hotels-Shepherds-Hut-With-Hot-Tub-Retreat.h97353427.Hotel-Information)

White Waltham

CA $333

CA $493 total

includes taxes & fees

Feb 15 - Feb 16

[](https://www.expedia.ca/Maidenhead-Hotels-Shepherds-Hut-With-Hot-Tub-Retreat.h97353427.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/124000000/123810000/123803000/123802932/83419d00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/124000000/123810000/123803000/123802932/7b0c5582_edited_2883.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, coffee/tea maker, dining tables](https://images.trvl-media.com/lodging/124000000/123810000/123803000/123802932/eea414f0_edited_730d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/124000000/123810000/123803000/123802932/8c4b4340_edited_0cf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Heartwarming Windsor Cottage with Free Parking

[](https://www.expedia.ca/Windsor-Hotels-Heartwarming-Windsor-Cottage-With-Free-Parking.h123802932.Hotel-Information)

Clewer East

CA $185

CA $342 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Windsor-Hotels-Heartwarming-Windsor-Cottage-With-Free-Parking.h123802932.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/123000000/122090000/122081100/122081021/a3a7a953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/123000000/122090000/122081100/122081021/83f36296.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/123000000/122090000/122081100/122081021/63029ad1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/123000000/122090000/122081100/122081021/686a5fec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Nayla House – Cozy 4BR with Garden & Parking

[](https://www.expedia.ca/Maidenhead-Hotels-Nayla-House-Cozy-4BR-With-Garden-Parking.h122081021.Hotel-Information)

Berkshire

CA $443

CA $547 total

includes taxes & fees

Feb 13 - Feb 14

[](https://www.expedia.ca/Maidenhead-Hotels-Nayla-House-Cozy-4BR-With-Garden-Parking.h122081021.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/126000000/125780000/125779500/125779461/d8db147f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/126000000/125780000/125779500/125779461/d054fd4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/126000000/125780000/125779500/125779461/46a5559b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/126000000/125780000/125779500/125779461/647b5d59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Maidenhead 6 Bed|Free Parking • Sleeps 12

[](https://www.expedia.ca/Maidenhead-Hotels-Maidenhead-6-BedFree-Parking-Sleeps-12.h125779461.Hotel-Information)

Maidenhead

CA $322

CA $543 total

includes taxes & fees

Feb 13 - Feb 14

[](https://www.expedia.ca/Maidenhead-Hotels-Maidenhead-6-BedFree-Parking-Sleeps-12.h125779461.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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Condos

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Private vacation homes

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Villas

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Cottages

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Residences

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Cabins

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Houseboats

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Chalets

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## Top Windsor and Maidenhead Hotel Reviews

![Thames Riviera Hotel, Sure Hotel Collection by Best Western](https://images.trvl-media.com/lodging/9000000/8190000/8183500/8183478/656d0531_y.jpg)

### Thames Riviera Hotel, Sure Hotel Collection by Best Western

8/10 Good

"Yes"

[](https://expedia.ca/Maidenhead-Hotels-Thames-Riviera-Hotel.h8183478.Hotel-Information)

![Castle Hotel Windsor](https://images.trvl-media.com/lodging/1000000/20000/16500/16500/a61d75bf_y.jpg)

### Castle Hotel Windsor

10/10 Excellent

"Staff were helpful and courteous. Room was clean and a good size."

[](https://expedia.ca/Windsor-Hotels-Castle-Hotel-Windsor-MGallery.h16500.Hotel-Information)

![Sir Christopher Wren Hotel](https://images.trvl-media.com/lodging/1000000/50000/47800/47781/148298d0_y.jpg)

### Sir Christopher Wren Hotel

10/10 Excellent

"A beautiful hotel, fantastic location with great facilities and staff. Will definitely go there again."

[](https://expedia.ca/Windsor-Hotels-Sir-Christopher-Wren-Hotel.h47781.Hotel-Information)

![Macdonald Compleat Angler](https://images.trvl-media.com/lodging/1000000/20000/16100/16055/a0245bf1_y.jpg)

### Macdonald Compleat Angler

10/10 Excellent

"Lovely stay, in a beautiful setting :)"

[](https://expedia.ca/Marlow-Hotels-Macdonald-Compleat-Angler.h16055.Hotel-Information)

![De Vere Beaumont Estate](https://images.trvl-media.com/lodging/2000000/1780000/1775700/1775624/e2fc3664_y.jpg)

### De Vere Beaumont Estate

10/10 Excellent

"Amazing hotel and location. Staff were incredibly friendly and helpful. The pool and gym are excellent! Only downside to the bar is the don’t have Guinness on draft"

[](https://expedia.ca/Windsor-Hotels-De-Vere-Beaumont-Estate.h1775624.Hotel-Information)

![Goswell House](https://images.trvl-media.com/lodging/58000000/57760000/57751800/57751774/17dfc26d_y.jpg)

### Goswell House

10/10 Excellent

"Just a sokod experience, start to finish. Super easy, helpful. Great location and room."

[](https://expedia.ca/Windsor-Hotels-Goswell-House.h57751774.Hotel-Information)

![Macdonald Berystede Hotel](https://images.trvl-media.com/lodging/1000000/20000/15600/15558/ea77019f_y.jpg)

### Macdonald Berystede Hotel

10/10 Excellent

"Yes"

[](https://expedia.ca/Ascot-Hotels-Macdonald-Berystede-Hotel.h15558.Hotel-Information)

![The Olde Bell, BW Signature Collection](https://images.trvl-media.com/lodging/1000000/50000/47600/47528/de366a17_y.jpg)

### The Olde Bell, BW Signature Collection

10/10 Excellent

"We stayed at The Olde Bell for one night and we were very kindly given an upgrade to a gorgeous luxury room overlooking the lovely garden. The room was very spacious and nicely decorated with a free standing bath in the room as well as a large walk in shower in the bathroom. The staff were all very friendly, dinner was good and breakfast was fantastic. This is also such a good value historical hotel in a gorgeous village. We will definitely be back - this is our second stay. "

[](https://expedia.ca/Maidenhead-Hotels-The-Olde-Bell.h47528.Hotel-Information)

![Monkey Island Estate - Small Luxury Hotels of the World](https://images.trvl-media.com/lodging/23000000/22580000/22580000/22579964/8d147782_y.jpg)

### Monkey Island Estate - Small Luxury Hotels of the World

10/10 Excellent

"Staff incredibly friendly, fantastic breakfasts too. Plenty of parking, wonderful location. "

[](https://expedia.ca/Maidenhead-Hotels-Monkey-Island-Estate.h22579964.Hotel-Information)

## Find out more about Windsor and Maidenhead

**Everything you need to know about** **Windsor and Maidenhead** **vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor and Maidenhead vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor and Maidenhead vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

**Windsor and Maidenhead vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Windsor and Maidenhead. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor and Maidenhead vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. The selection of Windsor and Maidenhead vacation rentals we have selected for you start as low as CA $227 per night. Entering your travel dates in the search wizard you might find even better deals!

**How to find incredible deals on Windsor and Maidenhead rentals**

At Expedia, we put the best Windsor and Maidenhead vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor and Maidenhead rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor and Maidenhead vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor and Maidenhead. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

## Explore a world of travel with Expedia

- Popular Windsor and Maidenhead Cities

- [Horton Vacation Rentals ](https://expedia.ca/Horton-Vacation-Rentals.d553248623058529209.Travel-Guide-VacationRentals)
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