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Windsor and Maidenhead Vacation Rentals

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Our top choices for Windsor and Maidenhead vacation rentals

A modern house with a dark exterior, a patio with outdoor furniture, and a white umbrella.

1. Willow Court Farm

Willow Court Farm
4.0 star property
Windsor
10.0 out of 10, Exceptional, (213 reviews)
"Very nice, comfortable room, nice to have the kitchen. Lots of space outside to eat and relax! The kids loved the animals and that it’s clise to Legoland! The restaurant near by was really nice too and also easy to get around without a car."
Canada
Anne
The price is CA $290
CA $348 total
includes taxes & fees
Sep 6 - Sep 7
Willow Court Farm
A cozy living room with a green sofa, a decorative tapestry, and a high ceiling with exposed beams.

2. Copper Castle & Petting Farm near Legoland

Copper Castle & Petting Farm near Legoland
4.0 star property
Windsor
10.0 out of 10, Exceptional, (4 reviews)
"Fantastic accommodation and setting. We loved our stay in the copper castle. The hosts have thought of everything to make your stay as enjoyable as possible and the goats outside the accommodation are very friendly!"
United Kingdom
HAYLEY
The price is CA $333
CA $399 total
includes taxes & fees
Sep 6 - Sep 7
Copper Castle & Petting Farm near Legoland
A modern kitchen with a central island, pendant lighting, and a view of the city through large windows.

3. Hampden Apartments - The Louis

Hampden Apartments - The Louis
3.0 star property
Eton
9.8 out of 10, Exceptional, (13 reviews)
"Great location especially having free parking. The apartment was very clean and modern."
United Kingdom
Lucy
The price is CA $239
CA $287 total
includes taxes & fees
Sep 6 - Sep 7
Hampden Apartments - The Louis
A bedroom with a bed, a dresser, a window, and a chandelier.

4. Spacious, light apartment sleeps up to four

Spacious, light apartment sleeps up to four
Cookham
9.6 out of 10, Exceptional, (19 reviews)
"Beautifully refurbished property with very helpful hosts."
United Kingdom
Alexandra C.
The price is CA $186
CA $392 total
includes taxes & fees
Aug 23 - Aug 24
Spacious, light apartment sleeps up to four
A neatly made bed with a grey quilt, a tray with croissants and orange juice, and a window with a view of houses.

5. Hampden Apartments - the Diana

Hampden Apartments - the Diana
4.0 star property
Windsor City Centre
9.2 out of 10, Wonderful, (46 reviews)
"The host provided very clear instructions regarding check-in/out. The property was exactly as expected and ideal for the purpose of our trip"
United Kingdom
Craig
The price is CA $291
CA $291 total
includes taxes & fees
Aug 27 - Aug 28
Hampden Apartments - the Diana
A modern living room with a flat-screen TV, a sofa, and a coffee table. There is a kitchen area with a dining table and bar stools.

6. Hampden Apartments - The George

Hampden Apartments - The George
4.0 star property
Windsor City Centre
9.2 out of 10, Wonderful, (37 reviews)
"Amazing location, walking distance to shops, restaurants, the theatre and of course the castle. The apartment was clean on arrival and had everything we needed for our stay. "
United Kingdom
Alison
The price is CA $432
CA $432 total
includes taxes & fees
Aug 30 - Aug 31
Hampden Apartments - The George
A modern kitchen with a central island, recessed lighting, and a view to the outside.

7. Stunning Central Windsor Town House

Stunning Central Windsor Town House
3.0 star property
Windsor City Centre
9.6 out of 10, Exceptional, (4 reviews)
"The house was perfect! The standard of the accommodation was excellent and it was located close to restaurants and all local attractions."
United Kingdom
Lisa
The price is CA $336
CA $758 total
includes taxes & fees
Aug 30 - Aug 31
Stunning Central Windsor Town House
A wooden interior with a kitchen, a chandelier, a TV, and a trash bin.

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

A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.
Old Windsor
9.4 out of 10, Exceptional, (10 reviews)
"Lovely Cabin"
United Kingdom
John W.
The price is CA $211
CA $241 total
includes taxes & fees
Sep 2 - Sep 3
A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.
A bedroom with a large bed, two bedside tables, a tray with breakfast, and a view of the sea through the window.

9. Hampden Apartments - The Henry

Hampden Apartments - The Henry
4.0 star property
Windsor City Centre
9.0 out of 10, Wonderful, (22 reviews)
"Loved our stay great location. Apartment was clean and prepared for our visit. The property could use a few repairs but altogether it was a great place to stay. "
United States
Jeremy
The price is CA $353
CA $353 total
includes taxes & fees
Aug 23 - Aug 24
Hampden Apartments - The Henry
A modern kitchen with a central island, two bar stools, a stainless steel range hood, and a window with blinds.

10. Hampden Apartments - The William

Hampden Apartments - The William
3.0 star property
Eton
9.0 out of 10, Wonderful, (19 reviews)
"Fantastic location and spotlessly clean. We really enjoyed our stay "
United Kingdom
Ian
The price is CA $182
CA $219 total
includes taxes & fees
Aug 23 - Aug 24
Hampden Apartments - The William
A cozy bedroom with a large bed, a grey sofa, a patterned rug, a window with curtains, and a fireplace.

11. Windsor Castle Amazing Cottage | 2-Min Walk | Central & Stylish

Windsor Castle Amazing Cottage | 2-Min Walk | Central & Stylish
Windsor City Centre
8.0 out of 10, Very good, (1 review)
"The house was very clean and a great location! We appreciated the provided fans throughout the house. Bathroom was well kept with shower toiletries available. We had to reach out to the host on the day of check in for access codes. We had to search for the Wifi information when there was no response for days from the host. Parking is not included, but there is a paid lot nearby. Since we stayed during the hot summer, the smells from trash were hard to tolerate. Overall, we would stay here...
United States
Susan
The price is CA $338
CA $513 total
includes taxes & fees
Aug 24 - Aug 25
Windsor Castle Amazing Cottage | 2-Min Walk | Central & Stylish
A modern loft apartment with a dining area, kitchen, and living space.

12. Hampden apartments - The Richard

Hampden apartments - The Richard
4.0 star property
Windsor City Centre
8.8 out of 10, Excellent, (12 reviews)
"We had a fabulous overnight stay, the location was perfect and I would highly recommend staying here - Thank you!"
United States
Pamela
The price is CA $369
CA $369 total
includes taxes & fees
Sep 6 - Sep 7
Hampden apartments - The Richard
A modern kitchen with a central island, pendant lighting, and a dining area with a glass table.

13. Fabulous Central Windsor Town House

Fabulous Central Windsor Town House
3.0 star property
Windsor City Centre
10.0 out of 10, Exceptional, (1 review)
"House is exactly as in the pictures. Lovely, spacious and clean. Kids loved the bunk bed. "
United Kingdom
Abdullah
The price is CA $471
CA $780 total
includes taxes & fees
Aug 25 - Aug 26
Fabulous Central Windsor Town House
A modern house with a patio, a garden with various plants, and a wooden deck.

14. Relaxing guest house with Jacuzzi & boat hire

Relaxing guest house with Jacuzzi & boat hire
Wraysbury
10.0 out of 10, Exceptional, (18 reviews)
"We had a lovely stay! The hot tub was fantastic, and the boat was absolutely fabulous. We really enjoyed ourselves and had a wonderful time. Thank you for a great stay!"
United Kingdom
Chaim
The price is CA $429
CA $476 total
includes taxes & fees
Aug 24 - Aug 25
Relaxing guest house with Jacuzzi & boat hire
A living room with a fireplace, sofa, and dining area.

15. Stylish 2-Bed Apartment in the Heart of Windsor – Walk to Windsor Castle

Stylish 2-Bed Apartment in the Heart of Windsor – Walk to Windsor Castle
Windsor City Centre
The price is CA $507
CA $706 total
includes taxes & fees
Aug 23 - Aug 24
Stylish 2-Bed Apartment in the Heart of Windsor – Walk to Windsor Castle
A modern living room with a grey sofa, a glass coffee table with orange juice, and a large window with a view of stone buildings.

16. Central Apartment Facing Windsor Castle

Central Apartment Facing Windsor Castle
4.0 star property
Windsor City Centre
8.6 out of 10, Excellent, (29 reviews)
"Quintessential English charm. Liked the location and view. Would suggest for a family vacation."
United States
Keith
The price is CA $381
CA $381 total
includes taxes & fees
Aug 28 - Aug 29
Central Apartment Facing Windsor Castle
A modern house with a patio, a garden with various plants, and a wooden deck.

17. Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire

Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire
3.0 star property
Wraysbury
10.0 out of 10, Exceptional, (1 review)
The price is CA $358
CA $486 total
includes taxes & fees
Aug 24 - Aug 25
Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire
A modern kitchen with a blue accent wall, wooden staircase, and a dining area with a table set for four.

18. Heartwarming Windsor Cottage with Free Parking

Heartwarming Windsor Cottage with Free Parking
Clewer East
10.0 out of 10, Exceptional, (1 review)
"Beautiful place to stay."
United States
Anonymous traveller
Heartwarming Windsor Cottage with Free Parking
A bedroom with a bed, a desk, a chair, a window, and a balcony.

19. Hampden Apartments - The Edward

Hampden Apartments - The Edward
3.5 star property
Windsor City Centre
7.8 out of 10, Good, (7 reviews)
"Enjoyed the stay "
United Kingdom
david
The price is CA $219
CA $262 total
includes taxes & fees
Aug 27 - Aug 28
Hampden Apartments - The Edward
A historic building with a central courtyard, a fountain, and a clock tower.

20. Character Victorian apartment close to Windsor town with secure parking

Character Victorian apartment close to Windsor town with secure parking
Clewer East
8.0 out of 10, Very good, (2 reviews)
"A gorgeous opulent place to stay while in Windsor. We appreciated the extra touches like the fresh milk for tea!"
Canada
Isabel
The price is CA $335
CA $402 total
includes taxes & fees
Aug 26 - Aug 27
Character Victorian apartment close to Windsor town with secure parking
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor and Maidenhead Hotel Reviews

Macdonald Windsor Hotel

Macdonald Windsor Hotel

10/10 Excellent
"Clean facilities. Daily room cleaning offered. Calm hotel friendly staff, superb location."
Adam 4-night trip
Posted less than an hour ago
Macdonald Windsor Hotel

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, 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 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 $241 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.