A group of guards in red uniforms with black hats and white gloves, marching with musical instruments.

Vacation Rentals in Windsor and Maidenhead

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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
The price is ￥40,809
￥48,971 total
includes taxes & fees
Nov 3 - Nov 4
Willow Court Farm
A bedroom with a bed, a dresser, a window, and a chandelier.

2. 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 ￥20,806
￥44,344 total
includes taxes & fees
Nov 1 - Nov 2
Spacious, light apartment sleeps up to four
A neatly made bed with two pillows, a bedside table with a lamp, and a bedside table with a decorative item.

3. The Fox at Hurley - Delightful Property!

The Fox at Hurley - Delightful Property!
Maidenhead
The price is ￥13,030
￥30,894 total
includes taxes & fees
Nov 1 - Nov 2
The Fox at Hurley - Delightful Property!
A cozy living room with a green sofa, a decorative tapestry, and a high ceiling with exposed beams.

4. 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
The price is ￥39,476
￥47,371 total
includes taxes & fees
Nov 1 - Nov 2
Copper Castle & Petting Farm near Legoland
A modern living room with a glass coffee table, a sofa with patterned cushions, and a dining area with a metal chair and a vase of flowers.

5. Hampden Apartments - The Catherine

Hampden Apartments - The Catherine
4.0 star property
Windsor City Centre
9.8 out of 10, Exceptional, (7 reviews)
"Brilliant stay, excellent location."
United Kingdom
Sophie
The price is ￥38,841
￥38,841 total
includes taxes & fees
Nov 1 - Nov 2
Hampden Apartments - The Catherine
A spacious living room with a dark sofa, a wooden coffee table, and a patterned rug.

6. Luxury 2 Bedroom Apartment

Luxury 2 Bedroom Apartment
Clewer North
The price is ￥28,036
￥48,002 total
includes taxes & fees
Nov 11 - Nov 12
Luxury 2 Bedroom Apartment
A modern kitchen with a central island, two bar stools, a stainless steel range hood, and a window with blinds.

7. Hampden Apartments - The William

Hampden Apartments - The William
3.0 star property
Eton
9.2 out of 10, Wonderful, (23 reviews)
"Always a lovely place to stay "
United Kingdom
Tony
The price is ￥22,146
￥26,575 total
includes taxes & fees
Nov 15 - Nov 16
Hampden Apartments - The William
A narrow wooden pathway leading to a building with a checkered floor.

8. 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.
The price is ￥33,101
￥49,914 total
includes taxes & fees
Nov 3 - Nov 4
Lovely cottage in the heart of the picturesque village of Cookham
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
The price is ￥37,451
￥45,227 total
includes taxes & fees
Nov 2 - Nov 3
Character Victorian apartment close to Windsor town with secure parking
A modern loft apartment with a dining area, kitchen, and living space.

10. Hampden apartments - The Richard

Hampden apartments - The Richard
4.0 star property
Windsor City Centre
8.8 out of 10, Excellent, (13 reviews)
"Easy check in, apartment was clean and in a great location. Lots of amenities in quick walking distance along with local restaurants and takeaways. Well recommended"
United Kingdom
Zahier
The price is ￥38,544
￥38,544 total
includes taxes & fees
Nov 1 - Nov 2
Hampden apartments - The Richard
A modern house with a patio, a garden with various plants, and a wooden deck.

11. 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 ￥40,103
￥54,428 total
includes taxes & fees
Nov 1 - Nov 2
Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire
A cozy interior with striped sofas, a kitchen area, and a bed with a view.

12. Shepherds Hut with Hot Tub Retreat - By Tempstay

Shepherds Hut with Hot Tub Retreat - By Tempstay
White Waltham
The price is ￥39,051
￥57,158 total
includes taxes & fees
Nov 1 - Nov 2
Shepherds Hut with Hot Tub Retreat - By Tempstay
A modern house with a patio, a garden with various plants, and a wooden deck.

13. 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 ￥48,254
￥53,531 total
includes taxes & fees
Nov 6 - Nov 7
Relaxing guest house with Jacuzzi & boat hire
A bedroom with a large bed, two bedside tables, a tray with breakfast, and a view of the sea through the window.

14. Hampden Apartments - The Henry

Hampden Apartments - The Henry
4.0 star property
Windsor City Centre
9.0 out of 10, Wonderful, (23 reviews)
"Superb apartment very good location far enough away from noise close enough to walk to centre. Apartment could fo with a little TLC. To bring back up to superb throughout. Overall a great stay"
United Kingdom
Dave
The price is ￥42,683
￥42,683 total
includes taxes & fees
Nov 1 - Nov 2
Hampden Apartments - The Henry
A modern kitchen with a blue accent wall, wooden staircase, and a dining area with a table set for four.

15. 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
The price is ￥33,643
￥51,507 total
includes taxes & fees
Oct 31 - Nov 1
Heartwarming Windsor Cottage with Free Parking
A modern kitchen with a wooden countertop, a grey sofa, and a blue accent wall.

16. 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.
The price is ￥26,270
￥36,148 total
includes taxes & fees
Nov 2 - Nov 3
Windsor Home with Free Parking
A brick building with arched windows and a sign reading "Côte Brasserie".

17. Windsor Castle panoramic views. Stay in the heart of Royal history

Windsor Castle panoramic views. Stay in the heart of Royal history
Eton
The price is ￥95,179
￥119,665 total
includes taxes & fees
Nov 6 - Nov 7
Windsor Castle panoramic views. Stay in the heart of Royal history
A modern kitchen with a marble countertop, a dining area with a white sofa, and a large window providing natural light.

18. Coronation Collection · Luxury 3BR - By Tempstay

Coronation Collection · Luxury 3BR - By Tempstay
Ascot
The price is ￥77,550
￥114,442 total
includes taxes & fees
Nov 1 - Nov 2
Coronation Collection · Luxury 3BR - By Tempstay
A bedroom with a window, a bed with pillows, and a lamp.

19. Ascot Racecourse Apartment

Ascot Racecourse Apartment
Ascot
The price is ￥20,806
￥33,416 total
includes taxes & fees
Nov 8 - Nov 9
Ascot Racecourse Apartment
A modern bedroom with a bed, bedside table, lamp, and a TV.

20. Chic Studio Steps from Windsor Castle

Chic Studio Steps from Windsor Castle
Windsor City Centre
10.0 out of 10, Exceptional, (2 reviews)
"Very Clean, property manager was very responsive and kind. Excellent customer service. I’ll stay here again."
United States
Ogonnaya L.
The price is ￥21,857
￥32,365 total
includes taxes & fees
Nov 5 - Nov 6
Chic Studio Steps from Windsor Castle
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor and Maidenhead Hotel Reviews

Macdonald Windsor Hotel

Macdonald Windsor Hotel

10/10 Excellent
"The perfect stay! I travelled as a large group for a special occasion. Hotel was in an ideal location, surrounded by lovely shops, cafes and restaurants. The concierge and reception staff were incredibly helpful 24/7 (before and during my stay.) Conference facilities looked lovely, the property was well maintained throughout, and I would recommend a stay to anyone."
Ruth 2-night trip
Posted 4 hours ago
Macdonald Windsor Hotel

Find out more about Windsor and Maidenhead

Vacation Apartments in Windsor and Maidenhead

Search for Vacation rentals in Windsor and Maidenhead on Expedia! You can easily find your home rentals, villas, Vacation apartments in Windsor and Maidenhead using one of the methods below:

  • View our selection of featured Vacation rentals in Windsor and Maidenhead
  • Use the map to find apartments and other Vacation homes in the Windsor and Maidenhead neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Windsor and Maidenhead while they last

Look no further and take a look at our great range of rental properties in Windsor and Maidenhead!