Windsor and Maidenhead Holiday Rentals

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Our top choices for Windsor and Maidenhead holiday rentals

Copper Castle & Petting Farm near Legoland

Copper Castle & Petting Farm near Legoland
4.0 star property
Windsor
10.0 out of 10, Exceptional, (1 review)
"The copper castle was an amazing place to stay, clean, comfortable, staff were amazing, children loved the animals and collecting egg's from the chickens in the morning. Owner's were very helpful and accommodating, will definitely be coming back for another stay."
United Kingdom
Susan
The price is AU$400
includes taxes & fees
5 June - 6 June
Copper Castle & Petting Farm near Legoland

Willow Court Farm

Willow Court Farm
4.0 star property
Windsor
10.0 out of 10, Exceptional, (205 reviews)
"Gorgeous self contained studio. My boys (aged 5 and 9) loved the built in bunk beds, and the fact they could collect fresh eggs and feed all the animals. Shaun and Angelica were so friendly, accomodated an earlier check in, and gave the boys plenty of animal feed! Only a 10min drive from Windsor Castle and Legoland, so perfect for our trip! The boys are already asking when we can return again! "
United Kingdom
Samantha
The price is AU$397
includes taxes & fees
2 June - 3 June
Willow Court Farm

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
9.8 out of 10, Exceptional, (7 reviews)
"Lovely Cabin"
United Kingdom
John W.
The price is AU$244
includes taxes & fees
24 May - 25 May
A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.

Windsor 5-bed House - Stroll to Castle - Sleeps 13

Windsor 5-bed House - Stroll to Castle - Sleeps 13
2.0 star property
Clewer North
6.0 out of 10, (1 review)
"Not walkable to the castle- unless you fast walk for 40mins! Not a short stroll as advertised - it’s in the middle of an estate (not so nice ) Make you pay £££ deposit or no check in details Make you sign this ridiculous document also to say if they had to take deposit off you because of damage- you can’t leave them a negative review! Got signs everywhere to remind you not to make noise/ switch off lights etc - doesn’t make us feel relaxed Strange smell in games room and first floor...
United Kingdom
Ho Yan Vivian
The price is AU$1,092
includes taxes & fees
2 June - 3 June
Windsor 5-bed House - Stroll to Castle - Sleeps 13

The Annex

The Annex
2.0 star property
Slough
The price is AU$987
includes taxes & fees
26 May - 27 May
The Annex

Relaxing guest house with Jacuzzi & boat hire

Relaxing guest house with Jacuzzi & boat hire
Wraysbury
10.0 out of 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
Wayne M.
The price is AU$476
includes taxes & fees
26 May - 27 May
Relaxing guest house with Jacuzzi & boat hire

Spacious, light apartment sleeps up to four

Spacious, light apartment sleeps up to four
Cookham
9.8 out of 10, Exceptional, (18 reviews)
"Beautifully refurbished property with very helpful hosts."
United Kingdom
Alexandra C.
The price is AU$393
includes taxes & fees
25 May - 26 May
Spacious, light apartment sleeps up to four

Cosy Lodge - Windsor Racecourse Marina By Tempstay

Cosy Lodge - Windsor Racecourse Marina By Tempstay
Clewer North
10.0 out of 10, Exceptional, (4 reviews)
"great place to stay"
United Kingdom
Kevin B.
The price is AU$776
includes taxes & fees
26 May - 27 May
Cosy Lodge - Windsor Racecourse Marina By Tempstay

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 AU$277
includes taxes & fees
28 May - 29 May
Hampden Apartments - The Louis

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 AU$296
includes taxes & fees
21 June - 22 June
Hampden Apartments - The Edward

Modern 2 Bed Oasis -Parking & Garden - By Tempstay

Modern 2 Bed Oasis -Parking & Garden - By Tempstay
Clewer North
Modern 2 Bed Oasis -Parking & Garden - By Tempstay

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 AU$486
includes taxes & fees
27 May - 28 May
Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire

Prince Consort Cottages, Windsor

Prince Consort Cottages, Windsor
Windsor City Centre
The price is AU$1,364
includes taxes & fees
18 June - 19 June
Prince Consort Cottages, Windsor

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

Vintage style Lodge In Windsor! Sleeps 15! Hot Tub!
Water Oakley
9.6 out of 10, Exceptional, (4 reviews)
"It was wonderful to stay all together as a family. Very clean, excellent communication from host, highly recommend!!!!"
United States
Trent B.
The price is AU$1,274
includes taxes & fees
28 May - 29 May
Vintage style Lodge In Windsor! Sleeps 15! Hot Tub!

Spacious 5 bed Sunninghill W/ Drive - By Tempstay

Spacious 5 bed Sunninghill W/ Drive - By Tempstay
Berkshire
10.0 out of 10, Exceptional, (1 review)
"Great spot. Five bdrm house in a nice quiet neighborhood that suited us perfectly. Could cook if you wanted but great restaurants within walking distance, particularly the Italian run by Adriano. We had a plumbing issue that was sorted the same day by the management co. Very happy with our choice."
United States
Scott D.
The price is AU$1,674
includes taxes & fees
17 June - 18 June
Spacious 5 bed Sunninghill W/ Drive - By Tempstay

Hampden Apartments - the Diana

Hampden Apartments - the Diana
4.0 star property
Windsor City Centre
9.2 out of 10, Wonderful, (45 reviews)
"Wonderful property! "
Canada
Meghan
The price is AU$289
includes taxes & fees
14 June - 15 June
Hampden Apartments - the Diana

Coventina

Coventina
3.0 star property
Wraysbury
The price is AU$4,464
includes taxes & fees
27 May - 28 May
Coventina

Character Victorian apartment close to Windsor town with secure parking

Character Victorian apartment close to Windsor town with secure parking
Clewer East
10.0 out of 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
Isabel
The price is AU$407
includes taxes & fees
31 May - 1 June
Character Victorian apartment close to Windsor town with secure parking

Royal Windsor Escape | Luxury 5 Acres Mansion, Helipad & Tennis Court

Royal Windsor Escape | Luxury 5 Acres Mansion, Helipad & Tennis Court
Horton
The price is AU$2,464
includes taxes & fees
25 May - 26 May
Royal Windsor Escape | Luxury 5 Acres Mansion, Helipad & Tennis Court

Stylish 3 Bed Cottage- Walk to Sights By Tempstay

Stylish 3 Bed Cottage- Walk to Sights By Tempstay
Windsor City Centre
9.0 out of 10, Wonderful, (4 reviews)
"Great easy access to all amenities including a local grocery store open until late at night. Would highly recommend this location"
United States
Sally S.
The price is AU$705
includes taxes & fees
26 May - 27 May
Stylish 3 Bed Cottage- Walk to Sights By Tempstay
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

Find out more about Windsor and Maidenhead

Everything you need to know about Windsor and Maidenhead holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor and Maidenhead holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Windsor and Maidenhead holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor and Maidenhead holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Windsor and Maidenhead holiday rentals we have chosen for you start as low as AU$244 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 holiday 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 holiday.

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.