A castle surrounded by lush gardens and a pond.

Vacation Rentals in Windsor and Maidenhead

Dates

November 2026

December 2026

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Our top choices for Windsor and Maidenhead vacation rentals

A modern building with dark siding, a glass door entrance, and two potted plants.

1. Willow Court Farm

Windsor

Anne

NT$6,361 total

includes taxes & fees

Nov 9 - Nov 10

A cozy living room with a green sofa, a decorative tapestry, and a high ceiling with exposed beams.

2. Copper Castle & Petting Farm near Legoland

Windsor

Susan

NT$7,019 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with a central island, two bar stools, a stainless steel range hood, and a window with blinds.

3. Hampden Apartments - The William

Eton

Tony

NT$5,873 total

includes taxes & fees

Nov 15 - Nov 16

A modern house with a patio, a garden with various plants, and a wooden deck.

4. Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire

Wraysbury

NT$11,361 total

includes taxes & fees

Nov 9 - Nov 10

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Find vacation rentals that suit your style

Top Windsor and Maidenhead Hotel Reviews

Willow Court Farm

Windsor

10/10 Excellent

michael

A cozy bedroom with a bed, bedside tables, a clock, and a window with curtains.

Park Farm Bed and Breakfast

Park

10/10 Excellent

Steven

An indoor swimming pool with lounge chairs and a glass wall.

Coworth Park - Dorchester Collection

Ascot

10/10 Excellent

From the pre-arrival concierge phone call from the UK to Canada asking whether I would like or need anything to enhance my stay and reminding me to bring my swimsuit to take advantage for the beautiful pool and spa to the last interaction at check-out - the Coworth Hotel is totally 5 star. The staff, ambience, grounds and wonderful staff are matchless. I travel frequently - and this experience topped the experience to date & has spoilt me for the future!

Heather

A bedroom with a patterned wallpaper, a striped headboard, a bed with multiple pillows, a chair, and two bedside tables with lamps.

Bel & The Dragon Cookham

Maidenhead

10/10 Excellent

Harriett

An outdoor patio area with round tables and chairs, a fire feature, and a view of the interior through large glass doors.

Monkey Island Estate - Small Luxury Hotels of the World

Maidenhead

10/10 Excellent

Beautiful little hotel in the cute little town of Bray. It was a delight, though dining at hotel was limited. I don't know why someone would choose to stay at an airport hotel when there is a wonderful place like this just a short drive away. Very convenient to Heathrow. Very romantic hotel. On an actual island, it was very nice in fall but I imagine it would be spectacular in summer. Only downside is no pool. Total delight!

Alice

A historic hotel with a classic facade, multiple windows, and a balcony with decorative railings.

Castle Hotel Windsor

Windsor City Centre

10/10 Excellent

Melanie

A neatly made bed with a black and white duvet, a wooden nightstand with a lamp, and a large mirror on the wall.

The Crown And Cushion

Eton

10/10 Excellent

constantine

A hotel room with a view of a historic castle.

Macdonald Windsor Hotel

Windsor City Centre

10/10 Excellent

Meriel

A bedroom with a large bed, two bedside tables, a tray with breakfast, and a view of the sea through the window.

Hampden Apartments - The Henry

Windsor City Centre

10/10 Excellent

Stacy

A large stone building with multiple chimneys, arched windows, and a well-maintained lawn.

Bisham Abbey National Sports Centre

Bisham

10/10 Excellent

inna

A hotel lobby with a wooden floor, a reception desk, and a dining area with chairs and tables.

Premier Inn Maidenhead Town Centre

Maidenhead

10/10 Excellent

John

A reception area with a wooden desk, a yellow sofa, and a round table with a vase of flowers.

The Royal Adelaide Hotel

Windsor City Centre

10/10 Excellent

Robert

A modern kitchen with a central island, recessed lighting, and a view to the outside.

Stunning Central Windsor Town House

Windsor City Centre

10/10 Excellent

JOEL

Find out more about Windsor and Maidenhead

Vacation Apartments in Windsor and Maidenhead

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Vacation Rentals in Windsor and Maidenhead

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor and Maidenhead vacation rentals

1. Willow Court Farm

2. Copper Castle & Petting Farm near Legoland

3. Hampden Apartments - The William

4. Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire

Find vacation rentals that suit your style

Top Windsor and Maidenhead Hotel Reviews

Willow Court Farm

10/10 Excellent

Find out more about Windsor and Maidenhead

Vacation Apartments in Windsor and Maidenhead