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Vacation Rentals in Windsor and Maidenhead

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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, (217 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
$176 nightly
The price is $212
Oct 14 - Oct 15
Total with taxes and fees
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, (5 reviews)
"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
$178 nightly
The price is $214
Oct 16 - Oct 17
Total with taxes and fees
Copper Castle & Petting Farm near Legoland
A white door with a sign reading "Cavendish House" and a fire access sign above it.

3. Cavendish House

Cavendish House
5.0 star property
Windsor City Centre
9.8 out of 10, Exceptional, (80 reviews)
"Fantaqstic Stay, I've been back a few times. Parking also, pays for itself."
United Kingdom
Anil
$244 nightly
The price is $293
Oct 16 - Oct 17
Total with taxes and fees
Cavendish House
A modern kitchen with a central island, two bar stools, a stainless steel range hood, and a window with blinds.

4. Hampden Apartments - The William

Hampden Apartments - The William
3.0 star property
Eton
9.0 out of 10, Wonderful, (20 reviews)
"Always a lovely place to stay "
United Kingdom
Tony
$126 nightly
The price is $151
Oct 13 - Oct 14
Total with taxes and fees
Hampden Apartments - The William
A neatly made bed with two pillows, a bedside table with a lamp, and a bedside table with a decorative item.

5. The Fox at Hurley - Delightful Property!

The Fox at Hurley - Delightful Property!
Maidenhead
$195 nightly
The price is $195
Oct 13 - Oct 14
Total with taxes and fees
The Fox at Hurley - Delightful Property!
A bedroom with a bed, a dresser, a window, and a chandelier.

6. 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.
$279 nightly
The price is $279
Oct 13 - Oct 14
Total with taxes and fees
Spacious, light apartment sleeps up to four
A spacious living room with a dark sofa, a wooden coffee table, and a patterned rug.

7. Luxury 2 Bedroom Apartment

Luxury 2 Bedroom Apartment
Clewer North
$264 nightly
The price is $264
Nov 1 - Nov 2
Total with taxes and fees
Luxury 2 Bedroom Apartment
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.

8. 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
$268 nightly
The price is $268
Oct 21 - Oct 22
Total with taxes and fees
Hampden Apartments - The George
A historic building with a central courtyard, a fountain, and a clock tower.

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

Character Victorian apartment close to Windsor town with secure parking
Clewer East
8.8 out of 10, Excellent, (3 reviews)
"A gorgeous opulent place to stay while in Windsor. We appreciated the extra touches like the fresh milk for tea!"
Canada
Isabel
$285 nightly
The price is $285
Oct 13 - Oct 14
Total with taxes and fees
Character Victorian apartment close to Windsor town with secure parking
A modern house with a patio, a garden with various plants, and a wooden deck.

10. 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)
$286 nightly
The price is $343
Oct 14 - Oct 15
Total with taxes and fees
Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire
A narrow wooden pathway leading to a building with a checkered floor.

11. Lovely cottage in the heart of the picturesque village of Cookham

Lovely cottage in the heart of the picturesque village of Cookham
Cookham
10.0 out of 10, Exceptional, (1 review)
"Roseleigh Cottage is a lovely little house. It is ideally situated in central Cookham a stones throw from the Thames tow path and close to a range of pubs and other places to eat. The cottage is very well equipped and comfortable. We really enjoyed our stay as did our dog who appreciated the many walks thereabouts."
United States
Maggie L.
$314 nightly
The price is $314
Oct 13 - Oct 14
Total with taxes and fees
Lovely cottage in the heart of the picturesque village of Cookham
A balcony with a white chair, a small table, and a floor lamp.

12. Charming 1BR Apartment | Parking Included

Charming 1BR Apartment | Parking Included
Windsor City Centre
$306 nightly
The price is $306
Oct 28 - Oct 29
Total with taxes and fees
Charming 1BR Apartment | Parking Included
A modern kitchen with a wooden countertop, a grey sofa, and a blue accent wall.

13. Windsor Home with Free Parking

Windsor Home with Free Parking
Clewer South
10.0 out of 10, Exceptional, (1 review)
"A perfect location for visiting Legoland and Windsor Castle. Easy to find, parking is literally right outside of the front door and the apartment is fitted with everything you could need.We will definitely recommend and will use again if we visit Legoland again in the future."
United Kingdom
Ian G.
$226 nightly
The price is $226
Oct 14 - Oct 15
Total with taxes and fees
Windsor Home with Free Parking
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
$336 nightly
The price is $336
Oct 13 - Oct 14
Total with taxes and fees
Relaxing guest house with Jacuzzi & boat hire
A cozy bedroom with a large bed, a grey sofa, a patterned rug, a window with curtains, and a fireplace.

15. 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, (4 reviews)
"Great house. Perfect location. A wonderful stay."
United States
David T.
$308 nightly
The price is $308
Oct 13 - Oct 14
Total with taxes and fees
Windsor Castle Amazing Cottage | 2-Min Walk | Central & Stylish
A cozy interior with striped sofas, a kitchen area, and a bed with a view.

16. Shepherds Hut with Hot Tub Retreat - By Tempstay

Shepherds Hut with Hot Tub Retreat - By Tempstay
White Waltham
$355 nightly
The price is $358
Oct 13 - Oct 14
Total with taxes and fees
Shepherds Hut with Hot Tub Retreat - By Tempstay
A modern kitchen with a blue accent wall, wooden staircase, and a dining area with a table set for four.

17. 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 traveler
$295 nightly
The price is $295
Oct 13 - Oct 14
Total with taxes and fees
Heartwarming Windsor Cottage with Free Parking
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.

18. Central Apartment Facing Windsor Castle

Central Apartment Facing Windsor Castle
4.0 star property
Windsor City Centre
8.6 out of 10, Excellent, (31 reviews)
"Amazing location, lots of shops !! "
United States
Samantha
Central Apartment Facing Windsor Castle
A bedroom with a window, a bed with pillows, and a lamp.

19. Ascot Racecourse Apartment

Ascot Racecourse Apartment
Ascot
$205 nightly
The price is $205
Oct 14 - Oct 15
Total with taxes and fees
Ascot Racecourse Apartment
A modern living room with a flat-screen TV mounted on a wooden wall, a window with curtains, a wooden bench, and a framed picture on the wall.

20. Elegant Windsor Flat -Short Walk to Windsor Castle, River Thames &Train Station

Elegant Windsor Flat -Short Walk to Windsor Castle, River Thames &Train Station
Eton
10.0 out of 10, Exceptional, (3 reviews)
"Gorgeous flat in a perfect location. There were so great places to walk to, including Windsor Castle. Highly recommend this place!"
United States
jennifer j.
$249 nightly
The price is $249
Oct 14 - Oct 15
Total with taxes and fees
Elegant Windsor Flat -Short Walk to Windsor Castle, River Thames &Train Station
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 Compleat Angler

Macdonald Compleat Angler

8/10 Good
"Great location, right on the bridge so less than 5 mins walk to the high street, ample parking, just register your number plate with reception when you park. Rooms are lovely and spacious, bathrooms are dated but clean."
Jessica 1-night trip
Posted 17 hours ago
Macdonald Compleat Angler

Find out more about Windsor and Maidenhead

Discover your perfect Windsor and Maidenhead vacation rental with Expedia

How many vacation rentals are available in Windsor and Maidenhead?


Expedia has plenty of vacation rentals to choose from in and around  Windsor and Maidenhead, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Windsor and Maidenhead?


The selection of Windsor and Maidenhead vacation rentals we have selected for you start as low as $212 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Windsor and Maidenhead?


Vacation rentals in Windsor and Maidenhead come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Windsor and Maidenhead vacation rentals to suit everyone. 


Why should I choose a vacation rental in Windsor and Maidenhead?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. 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. 


How do I find the best deal on a vacation rental in Windsor and Maidenhead?


Find vacation rentals in Windsor and Maidenhead by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Windsor and Maidenhead.  


What amenities are available in a vacation rental in Windsor and Maidenhead?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Windsor and Maidenhead vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Windsor and Maidenhead?   


Everytime is a great time to head to Windsor and Maidenhead! Staying in a Windsor and Maidenhead vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Windsor and Maidenhead. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Windsor and Maidenhead vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Windsor and Maidenhead, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Windsor and Maidenhead vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.