Holiday Rentals in Windsor and Maidenhead

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Featured Holiday Rentals in Windsor and Maidenhead

Our top choices for Windsor and Maidenhead holiday rentals

SnoozeDen Westmead – Windsor Castle & Legoland
Exterior

SnoozeDen Westmead – Windsor Castle & Legoland

3.0 star property
4.6 out of 10, (9)
"Great location, on the heathrow flight path which we knew, easy parking, and good comms. "
The price is €68
includes taxes & fees
29 Sept - 30 Sept
SnoozeDen Westmead – Windsor Castle & Legoland
Willow Court Farm
Exterior detail

Willow Court Farm

4.0 star property
10.0 out of 10, Exceptional, (196)
"This place is outstanding, the farm make your stay very welcome."
The price is €181
includes taxes & fees
28 Sept - 29 Sept
Willow Court Farm
Royal Windsor Estate | 5 Acres of Lush Green Gardens, Luxury Stay & Helipad
Exterior

Royal Windsor Estate | 5 Acres of Lush Green Gardens, Luxury Stay & Helipad

The price is €1,619
includes taxes & fees
29 Sept - 30 Sept
Royal Windsor Estate | 5 Acres of Lush Green Gardens, Luxury Stay & Helipad
King Edward Apartments
Apartment | Private kitchen

King Edward Apartments

4.5 star property
9.6 out of 10, Exceptional, (67)
"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. "
King Edward Apartments
Stay,work, Relax Ideal for Crews and Long Stays
House | Private kitchen

Stay,work, Relax Ideal for Crews and Long Stays

2.0 star property
Stay,work, Relax Ideal for Crews and Long Stays
Hampden Apartments - The Anne
Deluxe Apartment | Living area

Hampden Apartments - The Anne

3.5 star property
9.2 out of 10, Wonderful, (5)
"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! "
Hampden Apartments - The Anne
Luxury Ascot Escape- Indoor Hydro Pool & Wellness Spa
Exterior

Luxury Ascot Escape- Indoor Hydro Pool & Wellness Spa

The price is €2,259
includes taxes & fees
26 Sept - 27 Sept
Luxury Ascot Escape- Indoor Hydro Pool & Wellness Spa
Hampden Apartments - the Diana
Apartment, 1 Bedroom | Living area

Hampden Apartments - the Diana

4.0 star property
9.2 out of 10, Wonderful, (39)
"Wonderful property! "
Hampden Apartments - the Diana
Hampden Apartments - The Henry
Apartment, 3 Bedrooms | Private kitchen

Hampden Apartments - The Henry

4.0 star property
9.4 out of 10, Exceptional, (18)
"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. "
Hampden Apartments - The Henry
Hampden Apartments - The Louis
Interior

Hampden Apartments - The Louis

3.0 star property
9.6 out of 10, Exceptional, (10)
"Love the location and loved the flat. All was perfect for us. "
Hampden Apartments - The Louis
STABLE HOUSE - Near Windsor Castle
Garden

STABLE HOUSE - Near Windsor Castle

3.0 star property
9.4 out of 10, Exceptional, (12)
"I was traveling for three weeks for business and the Stable House was such a perfect home base - you really can't beat the location if you're looking for something in the area. It was clean, well maintained, and on a quiet side street but still minutes (literally just a few hundred feet) to good food and drink. And of course, only a few minutes walk to the Castle and the Windsor side of the river (only about a five minute walk to the castle)."
STABLE HOUSE - Near Windsor Castle
Hampden apartments - The Richard
Apartment, 2 Bedrooms | Balcony

Hampden apartments - The Richard

4.0 star property
8.8 out of 10, Excellent, (10)
"We had a fabulous overnight stay, the location was perfect and I would highly recommend staying here - Thank you!"
Hampden apartments - The Richard
Hampden Apartments - The William
Deluxe Apartment | Private kitchen

Hampden Apartments - The William

3.0 star property
9.4 out of 10, Exceptional, (9)
"We would definitely stay here again. Perfect location. Had parking and we were able to ealk everywhere. Thank you! "
Hampden Apartments - The William
Host Stay Eton House
Apartment

Host Stay Eton House

2.0 star property
Host Stay Eton House
Riverside home, Hot Tub/Sauna, Nr Legoland & Wakeboarding www. liquidleisure.com
Terrace/patio

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

8.4 out of 10, Very good, (145)
"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"
Riverside home, Hot Tub/Sauna, Nr Legoland & Wakeboarding www. liquidleisure.com
Gorgeous Country Cottage, beside Windsor Great Park & overlooking Windsor Castle
Outdoor dining

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

10.0 out of 10, Exceptional, (104)
"We had a wonderful time staying in this cozy cottage! The hosts were very receptive and communicative. The outside is just gorgeous :) Highly recommend"
Gorgeous Country Cottage, beside Windsor Great Park & overlooking Windsor Castle
Cavendish House
Garden

Cavendish House

5.0 star property
10.0 out of 10, Exceptional, (62)
"Fantastic stay with the family, perfect location, property and hosting"
Cavendish House
A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (3)
"Had a great stay prior to our flight home. They had everything we needed including things for the kids (1 and 3)."
The price is €151
includes taxes & fees
5 Oct - 6 Oct
A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.
Crazy Fox Garden Cabin - From 120 Per Night
Studio

Crazy Fox Garden Cabin - From 120 Per Night

2.0 star property
The price is €267
includes taxes & fees
2 Oct - 3 Oct
Crazy Fox Garden Cabin - From 120 Per Night
Stunning Central Windsor Town House
Deluxe House | Living area

Stunning Central Windsor Town House

3.0 star property
10.0 out of 10, Exceptional, (2)
"The property was in a nice quiet residential space but just minutes walking to shops, restaurants, etc. It was really perfect for what we were looking for."
Stunning Central Windsor Town House
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

Sir Christopher Wren Hotel

Sir Christopher Wren Hotel

10/10 Excellent
"I have stayed in countless hotels over the years but The Sir Christopher Wren has to be one of the best . The location was perfect, all of the staff were friendly and helpful and the food both at breakfast and for evening meals was top quality. I can`t find a single thing I wasn`t happy with. Dave Duff"
David 2-night trip
Posted 4 days ago
Sir Christopher Wren Hotel

Find out more about Windsor and Maidenhead

Find out more about Windsor and Maidenhead

Holiday Homes in Windsor and Maidenhead

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

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

Explore a world of travel with Expedia

Explore a world of travel with Expedia