Windsor and Maidenhead Holiday Rentals from NZ$278: Search Short-Term Rentals

Where will you be on 19 May 2018?

In Windsor Castle, attending the wedding of Prince Harry and Meghan Markle?

Or maybe in Wembley watching the FA Cup final?

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 holiday rentals

Willow Court Farm

Windsor

Zoe

includes taxes & fees

1 Feb - 2 Feb

Comfort Apartment, 2 Bedrooms, Non Smoking

Hampden Apartments - The George

Windsor City Centre

Timothy

Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire

Wraysbury

includes taxes & fees

1 Feb - 2 Feb

Relaxing guest house with Jacuzzi & boat hire

Wraysbury

Wayne M.

includes taxes & fees

10 Feb - 11 Feb

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

Old Windsor

Peyton T.

includes taxes & fees

4 Feb - 5 Feb

1 bedroom, individually decorated, individually furnished, free WiFi

Thames Retreat

Wraysbury

includes taxes & fees

7 Feb - 8 Feb

Spacious 5 bed Sunninghill with driveway parking

Berkshire

Scott D.

includes taxes & fees

5 Feb - 6 Feb

Character Victorian apartment close to Windsor town with secure parking

Clewer East

Isabel

includes taxes & fees

1 Feb - 2 Feb

View all properties

Find holiday rentals that suit your style

Aparthotels

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top Windsor and Maidenhead Hotel Reviews

Monkey Island Estate - Small Luxury Hotels of the World

10/10 Excellent

"Staff incredibly friendly, fantastic breakfasts too. Plenty of parking, wonderful location. "

Sir Christopher Wren Hotel

10/10 Excellent

"The only downside to the hotel is the lack of parking. Whilst you can pre-book reserved parking at the railway station it's a 5 minute walk away, so not ideal with luggage, particularly if it's raining. However, that won't put me off staying again as everything else about it is wonderful! Our room, which was an executive king size, was lovely and big and the bed was very comfortable and much bigger than our king size bed! The breakfast is self service and has a wide variety of pastries and cooked breakfast and even has a pancake maker, which I didn't try but I might next time! We ate in the restaurant one night and the food was very nice, with a good choice. The views of the river from the restaurant are lovely. We stayed because we were going to Windsor races and you can't get any closer to the promenade to catch the boat to the races! We also managed to get a last minute booking to go the Theatre Royal, which is a couple of minutes walk away. The hotel really is in a perfect position! All I would say is that if you struggle with stairs, make sure that you ask for a room on the level, or in their courtyard building rather than the main building. The main building doesn't have lifts (it's listed) and the stairs are windy. I will do that next time we go because my knees will thank me! We have stayed at two other hotels in Windsor, but I think that we will be staying here from now on. I don't think that it can be beaten for comfort, food and it's position."

Castle Hotel Windsor

10/10 Excellent

"I would recommend the castle hotel to everyone. Lovely hotel, great location and the staff were so friendly and helpful. On arrival to the hotel, I went to check in, and found I’d booked the wrong date, I was a week early. Expedia did nothing whatsoever to help me, apart from try to charge me the same price of the room again, to change my booking, even though I spend £1000s through them every year. It was my mistake, but I found Expedias response to the situation very disappointing. However, the lady on reception and someone from the reservations team…. I can’t remember either of their names, did everything they could to help and even got me a refund on the room that I incorrectly booked and I can’t thank them enough. If you ever stay in Windsor, then make sure you stay here "

Holiday Inn Express Windsor by IHG

10/10 Excellent

"This hotel far exceeded our expectations. The staff were the kindest, most conscientious, considerate, cheerful people we’ve ever seen in a hotel and they seemed to take great pride in their work. The breakfast was astounding both with the variety of offerings and the quality. The room was nice and had a sofa that we could both sit on whereas most king rooms only have one chair at other hotels. The heat in our room wasn’t working properly and they immediately sent up a portable heater. We’re already looking forward to coming back next year."

The Olde Bell, BW Signature Collection

10/10 Excellent

"The building is beautiful, filled with history. I booked a superior for the bath in the room. I was given a pleasant room in what I think is the original medieval part of the building but the bath was through a cool 'corridor' in the room. However, I spoke to the very assistive staff and they suggested a different room which I was absolutely delighted with! This room was unique, had 2 steps down to the bathroom, had a deep bath in the room, room was spacious but cosy and homely. The bed was very comfortable. The water was very hot, not scolding, but good temp. for a bath. The staff were very accommodating! Brought a radiator to the room for me, down to smallest details, even being short staffed on New Year's. They were also very attentive. Breakfast was good. Buffet of the usual English breakfast items, juice, toast with toppings and continental options. Parking just opposite. Also, lovely little village to take walks. Very pleased! Highly recommend."

Find out more about Windsor and Maidenhead

Everything you need to know about Windsor and Maidenhead holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor and Maidenhead holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor and Maidenhead holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor and Maidenhead holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor and Maidenhead. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor and Maidenhead holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor and Maidenhead holiday rentals we have selected for you start as low as NZ$278 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor and Maidenhead rentals

At Expedia, we put the best Windsor and Maidenhead holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor and Maidenhead rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor and Maidenhead holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor and Maidenhead. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Windsor and Maidenhead holiday rentals

Willow Court Farm

Hampden Apartments - The George

Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire

Relaxing guest house with Jacuzzi & boat hire

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

Thames Retreat

Spacious 5 bed Sunninghill with driveway parking

Character Victorian apartment close to Windsor town with secure parking

Fabulous Central Windsor Town House

Shepherds Hut with Hot Tub Retreat

SnoozeDen Westmead| Double Room

Windsor Home with Free Parking

Windsor Luxe Living – 3BR Near Windsor Castle

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

Spacious, light apartment sleeps up to four

Stylish 2-Bed House With Office And Private Garden

Nayla House – Cozy 4BR with Garden & Parking

Stay In Style With Castle Views/Prime Spot Windsor

Doorstep Of Windsor Castle Chic: 1BR|Parking

Heartwarming Windsor Cottage with Free Parking

Find holiday rentals that suit your style

Top Windsor and Maidenhead Hotel Reviews

Monkey Island Estate - Small Luxury Hotels of the World

Macdonald Compleat Angler

Macdonald Windsor Hotel

Goswell House

Sir Christopher Wren Hotel

The Royal Adelaide Hotel

Castle Hotel Windsor

Holiday Inn Express Windsor by IHG

The Olde Bell, BW Signature Collection

Find out more about Windsor and Maidenhead