Top Chalets in Windsor and Maidenhead in 2026

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Our top choices for Windsor and Maidenhead chalets

1. Cosy Cabin Close to Heathrow Airport, Windsor Castle, Legoland, Thorpe Park

Horton

Bruce S.

AED 762 total

includes taxes & fees

8 Sep - 9 Sep

2. Ascot Four Bedroom House With Garden

Ascot

3. Ascot Spacious 4 Bedroom Home with Driveway

Ascot

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Top Windsor and Maidenhead Hotel Reviews

Harte and Garter

10/10 Excellent

"Good nights sleep and a great location"

De Vere Beaumont Estate

8/10 Good

"Negatives: Lack of air-con in the room, poor changing facilities for the swimming pool (no privacy) and the Wi-Fi stopped working on our second evening, right through to the following morning. Positives: Family room was spacious, great food/drink selection at breakfast and the swimming pool itself was decent (and warm)."

The Crown And Cushion

10/10 Excellent

"Nice old pub with rooms. Stairs are steep and may be tricky with a heavy case. Decent carpark behind the pub, Nice cooked breakfast. The pub was shut when we returned about 21:30 but you can use the cark park entrance with the key provided. Very handy for Windsor High Street and the boat to the race track."

Oakley Court

10/10 Excellent

"Oakley Court is a beautiful hotel. The interiors manage to achieve both a sense of opulence and a feeling of being one’s own, at home. The spaces work equally well for a day time hang out but also provide cosy corner and fireplaces to sit alongside in the evening. Staff have a good balance of providing everything you need whilst still offering you privacy. We stayed in a Manor House room which are large on proportion, have a small seating area and lovely views of the gardens and river. We were also lucky enough to stay when the sun was shining and able to loose (willingly) hours to a watching the world go by on the lawn alongside the River. It gives a real sense of peace. The main Oakley Court menu is good but they also host guest chefs. Beyond the hotel there are a number of Michelin and Gastro style pubs that are a short taxi ride away. I’ve listed them on Instagram @takenbytoria It’s a would recommend and would return (hopefully soon)."

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Suv Car Rentals in Burnham

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor and Maidenhead chalets

1. Cosy Cabin Close to Heathrow Airport, Windsor Castle, Legoland, Thorpe Park

2. Ascot Four Bedroom House With Garden

3. Ascot Spacious 4 Bedroom Home with Driveway

Find vacation rentals that suit your style

Top Windsor and Maidenhead Hotel Reviews

Harte and Garter

The Royal Adelaide Hotel

De Vere Beaumont Estate

The Olde Bell, BW Signature Collection

Sir Christopher Wren Hotel

Macdonald Berystede Hotel

The Crown And Cushion

Macdonald Compleat Angler

Oakley Court

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