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

Holiday Homes in Windsor and Maidenhead

Compare and save
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Windsor and Maidenhead holiday homes

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

Windsor Castle Amazing Cottage | 2-Min Walk | Central & Stylish
Windsor City Centre
The price is £275
includes taxes & fees
2 Jul - 3 Jul
Windsor Castle Amazing Cottage | 2-Min Walk | Central & Stylish

Luxurious Central Windsor Town House

Luxurious Central Windsor Town House
4.0 star property
Windsor City Centre
8.4 out of 10, Very good, (7 reviews)
"The property was beautiful, well equipped and in a fantastic location. We had several questions for the owner who replied in good time, looking forward to revisiting in the future."
United Kingdom
Claire
Luxurious Central Windsor Town House

Stylish 4Bed Windsor Retreat - Garden - Sleeps 08

Stylish 4Bed Windsor Retreat - Garden - Sleeps 08
Park
Stylish 4Bed Windsor Retreat - Garden - Sleeps 08

4 Bed Windsor Countryside Escape - By Tempstay

4 Bed Windsor Countryside Escape - By Tempstay
Maidenhead
10.0 out of 10, Exceptional, (7 reviews)
"Excellent stay here in this lovely cottage. Pleasant area and close to Henley. "
United Kingdom
Chris A.
The price is £614
includes taxes & fees
23 Jul - 24 Jul
4 Bed Windsor Countryside Escape - By Tempstay

Cosy Double Room 5 Minutes from Station,Peaceful Area, Only 20 Minutes to London

Cosy Double Room 5 Minutes from Station,Peaceful Area, Only 20 Minutes to London
Maidenhead
10.0 out of 10, Exceptional, (1 review)
"The owner is super nice and loves dogs!! "
United States
Emily R.
Cosy Double Room 5 Minutes from Station,Peaceful Area, Only 20 Minutes to London

Immaculate Central Windsor Town House

Immaculate Central Windsor Town House
Windsor City Centre
10.0 out of 10, Exceptional, (15 reviews)
"Second stay in this spacious town house over Xmas"
United Kingdom
Jill W.
Immaculate Central Windsor Town House

Stylish 3 Bdr Home Central Windsor By Tempstay

Stylish 3 Bdr Home Central Windsor By Tempstay
Windsor City Centre
8.6 out of 10, Excellent, (8 reviews)
"We loved it, would stay here again.!!!"
United States
Leigh B.
Stylish 3 Bdr Home Central Windsor By Tempstay

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 £495
includes taxes & fees
6 Jul - 7 Jul
Cosy Lodge - Windsor Racecourse Marina By Tempstay

A stunning five-bedroom home located in the heart of Windsor driveway parking!

A stunning five-bedroom home located in the heart of Windsor driveway parking!
Windsor City Centre
9.4 out of 10, Exceptional, (3 reviews)
"IT WAS WONDERFUL FOR OUR FAMILY OF 10. THE BACK PORCH WAS WONDERFUL TO HAND OUT AT."
United States
shana m.
A stunning five-bedroom home located in the heart of Windsor driveway parking!

Nayla House – Cozy 4BR with Garden & Parking

Nayla House – Cozy 4BR with Garden & Parking
Berkshire
8.0 out of 10, Very good, (1 review)
"Good location. Easy access to airport"
United States
Lynn R.
The price is £302
includes taxes & fees
28 Jun - 29 Jun
Nayla House – Cozy 4BR with Garden & Parking

Windsor Gem: 1 Bed|1 Bath| Free Parking

Windsor Gem: 1 Bed|1 Bath| Free Parking
Windsor City Centre
10.0 out of 10, Exceptional, (1 review)
"Great looking apartment. "
United States
Michelle P.
The price is £176
includes taxes & fees
29 Jun - 30 Jun
Windsor Gem: 1 Bed|1 Bath| Free Parking

2BR Cottage|Parking |Close 2 Windsor - By Tempstay

2BR Cottage|Parking |Close 2 Windsor - By Tempstay
Datchet
8.0 out of 10, Very good, (1 review)
"The situation of the house is excellent. Easy to visit Windsor, Eton and Runnymede. "
United Kingdom
Gill H.
2BR Cottage|Parking |Close 2 Windsor - By Tempstay

Rainfall Shower | Pool/Snooker | x 4 Cars

Rainfall Shower | Pool/Snooker | x 4 Cars
Altwood
8.0 out of 10, Very good, (4 reviews)
"A decent place. Had everything we needed and would happily recommend."
United Kingdom
Darren A.
Rainfall Shower | Pool/Snooker | x 4 Cars

Stunning Central Windsor Town House

Stunning Central Windsor Town House
Windsor City Centre
10.0 out of 10, Exceptional, (3 reviews)
"Accommodation was excellent for us. Ideal location to walk into town. The train station for London was only a 10 minute walk away. All instructions were first class. We will definitely stay there again on our next visit next year. "
United Kingdom
Dave C.
Stunning Central Windsor Town House

Spacious 6 Bedroom House in Maidenhead/ Windsor

Spacious 6 Bedroom House in Maidenhead/ Windsor
Maidenhead
Spacious 6 Bedroom House in Maidenhead/ Windsor

Lovely 6-bed House in Windsor

Lovely 6-bed House in Windsor
3.0 star property
Old Windsor
Lovely 6-bed House in Windsor

Riverside bungalow, Hot Tub/Sauna, Nr Legoland, Windsor, Thorpe Park Theme Park.

Riverside bungalow, Hot Tub/Sauna, Nr Legoland, Windsor, Thorpe Park Theme Park.
Wraysbury
8.6 out of 10, Excellent, (159 reviews)
"Had a lovely stay"
United States
Abbie c.
Riverside bungalow, Hot Tub/Sauna, Nr Legoland, Windsor, Thorpe Park Theme Park.

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 £694
includes taxes & fees
29 Jun - 30 Jun
Vintage style Lodge In Windsor! Sleeps 15! Hot Tub!

Country House (East Wing) with Indoor Heated Pool and Basketball Court

Country House (East Wing) with Indoor Heated Pool and Basketball Court
Horton
10.0 out of 10, Exceptional, (6 reviews)
"Wonderful property, would love to stay again!"
United Kingdom
Jennifer D.
Country House (East Wing) with Indoor Heated Pool and Basketball Court

Central Windsor 2 BDR Retreat - By Tempstay

Central Windsor 2 BDR Retreat - By Tempstay
Windsor City Centre
8.8 out of 10, Excellent, (3 reviews)
"Nice place in central location "
United Kingdom
Dafydd H.
Central Windsor 2 BDR Retreat - 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windsor and Maidenhead Hotel Reviews

Find out more about Windsor and Maidenhead

Windsor and Maidenhead Holiday Homes: Find the Perfect Place


What is the best time to enjoy a holiday home in Windsor and Maidenhead?

It might be best to get a rental house in when the weather is ideal for enjoying local surroundings. If you go during the off-season months, there might be fewer tourists and often lower rates, like in .


How many holiday homes are available for rent in Windsor and Maidenhead?

Choose from 177 beautiful holiday homes in Windsor and Maidenhead for your getaway.


How much is a holiday home in Windsor and Maidenhead?

You can find perfect holiday homes in Windsor and Maidenhead for as low as £176 per night. Holiday home prices vary depending on what time of year you visit, whether the home is in the city centre or near popular sightseeing spots, and what kinds of amenities it offers.


How can I get the best deal on a holiday home in Windsor and Maidenhead?

Find the best deals on Windsor and Maidenhead holiday homes by entering dates and the number of travellers in the search bar. You can use the map feature to view prices and more specific locations of several accommodations all at once. Or filter your search results by star rating, price, number of bedrooms, types of amenities, and accessibility features—Expedia offers incredible deals for every budget.


Why should I book a holiday home in Windsor and Maidenhead?

There’s no better way to spend your well-earned holiday than in a private, cosy Windsor and Maidenhead holiday home. You’ll be able to fit all travellers in your group and have a place to call home while you explore Windsor and Maidenhead.


What amenities are available in a private holiday home?

Depending on your budget and the neighbourhood you choose, you’ll find amenities like a private pool, hot tub, free parking, a full-service kitchen or kitchenette, in-home laundry and WiFi. Your Windsor and Maidenhead holiday won’t be complete without a beautiful view and easy access to popular activities, use our filter to browse our offers.


Why should I book a holiday home with Expedia?

With Expedia, you’ll earn points on every booking and get incredible deals and member prices. Choose from a vast inventory of holiday homes in Windsor and Maidenhead—and book all your travel in one place. Save even more when you bundle your bookings together. Add a Windsor and Maidenhead car hire to your holiday property into a holiday package.


What are the cancellation and flexibility options?

We suggest using the “free cancellation” filter during your search to make sure your booking is flexible. Some accommodations accept and refund cancellations within a specific timeframe, while others may be non-refundable. Before you book, check your rental terms, or reach out to our customer service portal for further assistance.

Windsor and Maidenhead Holiday Homes information

Number of reviews
227
Accommodation
177 Holiday Homes
Lowest Price
£176
Highest Price
£694

Explore a world of travel with Expedia