Holiday Homes in Windsor and Maidenhead

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Our top choices for Windsor and Maidenhead holiday homes

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, (156 reviews)
"Had a lovely stay"
United States
Abbie c.
Riverside bungalow, Hot Tub/Sauna, Nr Legoland, Windsor, Thorpe Park Theme Park.

Victorian Cottage, Close 2 All Sights, Parking 🏰

Victorian Cottage, Close 2 All Sights, Parking 🏰
Clewer South
9.4 out of 10, Exceptional, (9 reviews)
"Cozy and comfortable house"
United States
David H.
Victorian Cottage, Close 2 All Sights, Parking 🏰

Luxurious Central Windsor Town House

Luxurious Central Windsor Town House
4.0 star property
Windsor City Centre
10.0 out of 10, Exceptional, (2 reviews)
"Everything was as I'd hoped for. Great location, lots of space, lovely bedrooms. The only fault I have was it advertised an iron and board. There wasn't an iron but there were three boards! "
United Kingdom
Yvonne
Luxurious Central Windsor Town House

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.
4 Bed Windsor Countryside Escape - By Tempstay

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
24 May - 25 May
Nayla House – Cozy 4BR with Garden & Parking

Stunning Central Windsor Town House

Stunning Central Windsor Town House
3.0 star property
Windsor City Centre
10.0 out of 10, Exceptional, (3 reviews)
"The house was perfect! The standard of the accommodation was excellent and it was located close to restaurants and all local attractions."
United Kingdom
Lisa
Stunning Central Windsor Town House

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 £459
includes taxes & fees
26 May - 27 May
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!

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

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 £220
includes taxes & fees
2 Jun - 3 Jun
Windsor Gem: 1 Bed|1 Bath| Free Parking

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

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.
The price is £434
includes taxes & fees
13 May - 14 May
Rainfall Shower | Pool/Snooker | x 4 Cars

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

Fabulous house on the river Thames riverside, near Windsor, Heathrow and London

Fabulous house on the river Thames riverside, near Windsor, Heathrow and London
Wraysbury
9.8 out of 10, Exceptional, (18 reviews)
"Lovely area right next to the river. Excellent property, perfect for a short stay."
United Kingdom
Edward L.
Fabulous house on the river Thames riverside, near Windsor, Heathrow and London

Historic River View Home in Windsor - By Tempstay

Historic River View Home in Windsor - By Tempstay
Clewer North
10.0 out of 10, Exceptional, (3 reviews)
"I booked this house for an extended family vacation - 4 couples, 1 single, and 2 babies. It was perfect! Huge, lovely, comfortable, perfectly situated. We had a fantastic time. Highly recommend."
United States
Patricia F.
Historic River View Home in Windsor - By Tempstay

Windsor 5-Bed House - Near Castle - Sleeps 13

Windsor 5-Bed House - Near Castle - Sleeps 13
Clewer North
Windsor 5-Bed House - Near Castle - Sleeps 13

Dual-Property Retreat in Windsor - By Tempstay

Dual-Property Retreat in Windsor - By Tempstay
Clewer North
10.0 out of 10, Exceptional, (2 reviews)
"The houses were beautiful. My daughter was getting married in the UK so 14 of the wedding party stayed at the house. The house is spacious and has a ton of history! The location was perfect with a fantastic walk along the river into the town. My only suggestion would have been to clean off outside furniture but other than that it was perfect. "
United States
yolande p.
Dual-Property Retreat in Windsor - By Tempstay

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 £683
includes taxes & fees
13 May - 14 May
Vintage style Lodge In Windsor! Sleeps 15! Hot Tub!

Family Home, beautiful view of Windsor Castle, 5 minute walk to shops and River

Family Home, beautiful view of Windsor Castle, 5 minute walk to shops and River
Eton
Family Home, beautiful view of Windsor Castle, 5 minute walk to shops and River

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
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

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 174 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 £220 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
228
Accommodation
174 Holiday Homes
Lowest Price
£220
Highest Price
£683

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