Top Condo Rentals in Windsor and Maidenhead in 2026

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Our top choices for Windsor and Maidenhead condo rentals

1 bedroom, iron/ironing board, WiFi, bed sheets

1. Charming Character Home| 1 Bed| By Tempstay

Windsor City Centre

2. Racing Royalty: 2-Bed, Ascot, Parking By Tempstay

Berkshire

3. ★ASCOT RACES★PERFECT SPOT TO EXPLORE WINDSOR/ASCOT

Berkshire

4. Luxury 2 Bedroom Apartment

Clewer North

SAR 948 total

includes taxes & fees

31 Aug - 1 Sep

5. Charming 1BR Apartment | Parking Included

Windsor City Centre

SAR 1,066 total

includes taxes & fees

25 Aug - 26 Aug

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Top Windsor and Maidenhead Hotel Reviews

Macdonald Windsor Hotel

8/10 Good

"Great location and wonderful breakfast There is a car park (£40) located under the hotel - very convenient although on the pricey side- that said our car was safe and the gentleman attending to the car park was lovely - he even offered us a complimentary bottle of water for our journey home."

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)."

The Olde Bell, BW Signature Collection

10/10 Excellent

"We received a warm welcome and enjoyed a super Sunday lunch. Our room was in excellent condition for our overnight stay and we enjoyed a good breakfast. Overall a lovely chilled stay in a quiet pretty village on the River Thames. Would we return? …. Certainly."

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor and Maidenhead condo rentals

1. Charming Character Home| 1 Bed| By Tempstay

2. Racing Royalty: 2-Bed, Ascot, Parking By Tempstay

3. ★ASCOT RACES★PERFECT SPOT TO EXPLORE WINDSOR/ASCOT

4. Luxury 2 Bedroom Apartment

5. Charming 1BR Apartment | Parking Included

Find vacation rentals that suit your style

Top Windsor and Maidenhead Hotel Reviews

Macdonald Windsor Hotel

The Royal Adelaide Hotel

Macdonald Compleat Angler

De Vere Beaumont Estate

Oakley Court

Castle Hotel Windsor

Fredrick's Hotel Restaurant & Spa

The Crown And Cushion

The Olde Bell, BW Signature Collection