Windsor Vacation Rentals from CA $106: Short-Term Rentals for 2025

Q: What's the top vacation rental in Windsor?

47 Park Street - Grand Residences by Marriott : Visitors like this Windsor vacation home rental. It is in the city center and equipped with air-conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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Vacation Rentals in Windsor

"Great location, on the heathrow flight path which we knew, easy parking, and good comms. "

CA $128 total

includes taxes & fees

Aug 17 - Aug 18

Relax under the shade of a large umbrella in a seating area surrounded by a decorative fence.

"love the farm , lovely pub walking distance from the place. "

CA $367 total

includes taxes & fees

Sep 9 - Sep 10

Kitchen features sleek cabinetry, stainless steel range hood, microwave, and a chair near the sink.

"Pretty clean, nice walk to town centre and transit. Parking a bit tight by North American standards. Lift available. Beds comfy and the owners/property managers as well as the cleaner were all wonderful. "

Enjoy a view of a historic building from the comfort of this room, featuring a large window, a neatly made bed, and a wall-mounted painting.

"Brilliant location and very helpful owner "

CA $457 total

includes taxes & fees

Aug 13 - Aug 14

Relax in this stylish living room with a sofa, coffee table, and flat-screen TV.

"Really nice apartment close to the centre of Windsor. Handy parking space close by that will save you some money as the local Q park is about £45 for 48 hours! "

CA $308 total

includes taxes & fees

Aug 15 - Aug 16

Enjoy a serene view of the water from the covered seating area, where you can relax and unwind.

"We rented this property for Christmas, and it was absolutely fantastic. The hosts were so friendly and there were lots of clear instructions on how to use the hot tub etc. The location was perfect, and we LOVED the decor of the place - so quirky and right up our street as we are a rock n roll loving family. We will be back 100%. Thank you to Andy & Sharon! xx"

Relax in this stylish living room with a comfortable sofa, a small table, and a beautiful view of the surrounding area.

"Wonderful property! "

CA $290 total

includes taxes & fees

Sep 7 - Sep 8

Enjoy cooking in this well-equipped kitchen with a central island and gas stove.

"We would definitely stay here again. Perfect location. Had parking and we were able to ealk everywhere. Thank you! "

CA $277 total

includes taxes & fees

Aug 21 - Aug 22

Enjoy cooking in this well-equipped kitchen with a gas stove, washing machine, and toaster.

"Where do I start The property was described as a studio. It stated that everyone in my party would be undestrurbed in the accomodation. This is untrue and breaches the trades description legislation The property has a shared kitchen with no privacy in it. The only TV is in the kitchen and so relaxing at the end of the day before bed by watching TV was not really possible My food had to be stored insecurely The access to the room I booked was up very steep steps with a low ceiling This...

Relax in this stylish living room with a sofa, side tables, and a comfortable armchair, offering a view of lush greenery outside.

"Good location for a group of friends to get to by road and rail for a reunion.A comfortable and relaxing venue for an overnight stay."

CA $1,551 total

includes taxes & fees

Sep 7 - Sep 8

Enjoy al fresco dining on the patio, surrounded by lush greenery and a brick wall.

"We had a wonderful time staying in this cozy cottage! The hosts were very receptive and communicative. The outside is just gorgeous :) Highly recommend"

Relax in this stylish living room with a sofa, coffee table, and dining area, offering a view of the city.

"Love the location and loved the flat. All was perfect for us. "

CA $290 total

includes taxes & fees

Aug 13 - Aug 14

Modern kitchen with sleek design, gas stove, and stainless steel range hood.

"Had an enjoyable 2 night stay. The property was cosy and welcoming. Shops just round the corner and only a 5 min drive to Legoland which was good."

Relax in a stylish living space with a light grey sofa, round side table, and warm rug.

"Good location with a very nice property"

Enjoy cooking in this well-lit kitchen with a gas range, stainless steel sink, and compact microwave.

CA $392 total

includes taxes & fees

Aug 10 - Aug 11

Enjoy cooking in this well-equipped kitchen with a central island and overhead lighting.

CA $644 total

includes taxes & fees

Aug 17 - Aug 18

CA $486 total

includes taxes & fees

Sep 1 - Sep 2

Enjoy cooking in this well-equipped kitchen with a central island, sink, and oven.

"great place to stay"

Relax in this serene bedroom with a large bed, flat-screen TV, and a bathroom with a toilet and sink.

Enjoy cooking in this well-equipped kitchen with a microwave, stainless steel range hood, and coffee maker.

"We wanted to beat the heat and enjoy the charming town of Windsor, comfortable apartment, great location, and a birthday weekend to boot. We would definitely stay again, quick communication and attentive booking."

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Top Windsor Hotel Reviews

Harte and Garter

10/10 Excellent

"We booked a castle-view room which was unreal. Walkability is 10/10. Room was spacious but not private if you like natural light as there is no sheer curtain on the window. Bed was firm and a bit cosy for two adults. Seamless check-in and check-out."

Castle Hotel Windsor

10/10 Excellent

"I stayed in the room with a city view and it was excellent, a lot of space, comfortable bed, nice bathroom, the white robes and white slippers are always creating an luxurious feel. Amazing selection of tea, coffee, water and milk in the mini fridge in the room. Will stay again next time I am in Windsor."

Macdonald Windsor Hotel

10/10 Excellent

"This hotel was fantastic. Beautiful hotel, with spacious rooms. It's almost directly across from the entrance to Windsor Castle, so it's perfect for visiting that and the town. No meals were included with our stay, so we had Eggs Benedict for breakfast at the restaurant next door, which was fantastic. My only complaint is their lack of parking! If you have a car then make sure you reserve a parking spot for the night! We were unaware of this upon arrival and ended up having to park in a pay lot down the street. It wasn't the end of the world obviously, just a bit inconvenient. But otherwise va lovely hotel "

Sir Christopher Wren Hotel

10/10 Excellent

"My opinion, this was a gem to find for a couple of days in Windsor. It's down the hill from the castle, so less noise and tour buses. I tend to like the quiet places where I can take a morning walk. If you are more of a fan of pubs, this hotel is a block away from 3 good pubs that are easily walkable. The staff was very attentive. I had help with my bags all the way to the room, help with umbrellas, directions, and even taking a river cruise. The breakfast was surprisingly good, and there was a self-service Espresso machine to make individual americanos or frothy cappuccinos. Booking with Expedia gave me a decent price for breakfast included. The view from the dining room overlooks the river and was tranquil in the morning. Overall, a very relaxing place. My wife and I used it for a couple of nights to adjust to the jet lag and relax before spending 11 days in Scotland and Ireland. "

Find out more about Windsor

Everything you need to know about Windsor 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 vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. 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 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 vacation rentals we have selected for you start as low as CA $106 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor 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 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 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 to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Can I find a vacation rental in Windsor?

Yes, we have vacation rentals in Windsor close to LEGOLAND® Windsor, or you can choose a more secluded option if you want a relaxing stay. Visitors like the array of shops and scenic riverfront in Windsor. While you're here, grab a bite or have a drink at the top-notch restaurants and lively bars.

What's the top vacation rental in Windsor?

47 Park Street - Grand Residences by Marriott: Visitors like this Windsor vacation home rental. It is in the city center and equipped with air-conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Windsor?

Choose from 100 Expedia vacation rentals in Windsor for a memorable vacation.

What’s there to see and do in Windsor?

LEGOLAND® Windsor and Queen Mary's Dolls' House are a couple of family-friendly sights, whereas cultural attractions include Frogmore House and Theatre Royal. You’ll find favorite places to visit like Wembley Stadium and Warner Bros. Studio Tour London in the larger area.

What’s a vacation rental in Windsor like?

Vacation rentals are privately owned properties where you can stay for short or long periods in Windsor. Vacation rentals feature extras like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for a family trip.

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Windsor Vacation Rentals

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Vacation Rentals in Windsor

SnoozeDen Westmead – Windsor Castle & Legoland

SnoozeDen Westmead – Windsor Castle & Legoland

Willow Court Farm

Willow Court Farm

King Edward Apartments

King Edward Apartments

Central Apartment Facing Windsor Castle

Central Apartment Facing Windsor Castle

Hampden Apartments - The Anne

Hampden Apartments - The Anne

Riverside home, Hot Tub/Sauna, Nr Legoland & Wakeboarding www. liquidleisure.com

Riverside home, Hot Tub/Sauna, Nr Legoland & Wakeboarding www. liquidleisure.com

Hampden Apartments - the Diana

Hampden Apartments - the Diana

Hampden Apartments - The William

Hampden Apartments - The William

Stunning 1-bed Studio in Windsor

Stunning 1-bed Studio in Windsor

Vintage style Lodge In Windsor! Sleeps 15! Hot Tub!

Vintage style Lodge In Windsor! Sleeps 15! Hot Tub!

Gorgeous Country Cottage, beside Windsor Great Park & overlooking Windsor Castle

Gorgeous Country Cottage, beside Windsor Great Park & overlooking Windsor Castle

Hampden Apartments - The Louis

Hampden Apartments - The Louis

Victorian Cottage, Close 2 All The Sights, Parking

Victorian Cottage, Close 2 All The Sights, Parking

Windsor Mews by Stay Focused SA

Windsor Mews by Stay Focused SA

Host Stay Eton House

Host Stay Eton House

Fabulous Central Windsor Town House

Fabulous Central Windsor Town House

Stay,work, Relax Ideal for Crews and Long Stays

Stay,work, Relax Ideal for Crews and Long Stays

Stylish Lodge At Windsor Racecourse Marina

Stylish Lodge At Windsor Racecourse Marina

Spacious 5-Bedroom Home in Windsor

Spacious 5-Bedroom Home in Windsor

Windsor Castle Apartments

Windsor Castle Apartments

Top Windsor Hotel Reviews

Harte and Garter

Find out more about Windsor

Find out more about Windsor

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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