
Holiday rentals in Maidenhead
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Top-rated holiday rentals in Maidenhead
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Five Star Boutique House near Windsor Castle, Ascot & London
This Grade 11 listed Mews property was built in 1872 and offers contemporary, luxurious living space. Luxurious king size beds, beautiful bathrooms, abundant art and character; the properties look onto an ancient courtyard with fountain, secure behind private gates with parking. The location is exceptional. Windsor Great Park is a 10 min stroll away, and Windsor is 3 miles away, Wentworth Golf Club and Ascot are all within 6 miles. Central London is 35 minutes by train. Heathrow is 6 miles away.

The Studio in Maidenhead Riverside, Berkshire, UK.
LARGE STUDIO: (T0) A large self-contained quiet studio with UK size 2m double bed, en-suite bathroom and kitchenette with it's own private entrance. Attached to our house. There is off-street parking for 1 guest car. Convenient for the A4, M4, M40 M25 London is 25 miles. Heathrow Airport is 15 minutes away by car.. Direct trains into London. The Elizabeth Line train runs from Maidenhead station direct to London and the West End. Good for Windsor, Ascot, River Thames, Pinewood Studios etc.

Charming terrace in the heart of Bray village
Our lovely victorian terraced home is perfectly situated for all the fine dining that the charming village of Bray has to offer. The Michelin 3-starred Waterside Inn and Fat Duck are a few mins walk away as are the Crown Inn, Hinds Head and Caldesi. Stroll 15 mins more and you’ll find the recently renovated Monkey Island Estate. A short drive and you can be at either Ascot or Windsor Races, Cliveden House, Legoland, the village of Cookham or the beautiful river Thames towns of Marlow or Henley

17th Century Barn in quiet country village
A 17th Century Hay Barn 7 miles from Oxford and in the same village as ‘Le Manoir aux Quat’ Saisons’. Enjoy a glass of bubbles on your own private terrace before strolling to dinner at this famous Cotswold stone Manor. Fully wheelchair accessible & with private parking this unique property is the perfect place for a few days away walking in the nearby Chilterns, exploring Oxford’s Colleges & Cafes, visiting Art & Literary Fairs or attending appointments at Oxford’s many leading hospitals.

A Hidden Gem
A character cottage, tucked away, in the heart of gastronomic Bray - renowned for its Michelin-starred restaurants: The Waterside, The Fat Duck, the Hind's Head and Caldesi, all within easy walking distance of the cottage. Lych Cottage is a two-bed semi-detached property, completed to a high standard. It provides a stylish place to stay for those wishing to enjoy the comforts of home whilst availing themselves of the local amenities. The first night's stay includes a continental breakfast.

Completely separate self-contained studio flat
Self-contained double room with en-suite shower room and kitchen area. Private access and parking. Completely private stand-alone studio but part of our home. Suitable for professional person/couple for short let periods. Ideal Monday-Friday but good for weekends to visit local area too. Free wi-fi, TV. A car is essential. Located in White Waltham village just outside Maidenhead. Easy access to Junction 8/9 of M4 and Maidenhead station. Also handy for Windsor, Henley, Ascot, Reading

2 Bedroom Luxury Cottage (Secure & Quiet)
This charming Cottage is located in the picturesque Village of Englefield Green. Just four miles from Windsor Castle, three miles from Wentworth Golf Course and six miles from Ascot Race Course. Heathrow Airport if just six miles away. 300 metres further down the lane is The Royal Air Force Memorial and below that, on National Trust grounds that skirts the River Thames is the Magna Carta Memorial. The Royal Holloway University is a ten minute stroll across the Village.

Hagrid Hut Themed - Hot Tub - Warner Bro Studio
Hagrid & Fang are away and would like you to watch over his home, located next to the Forbidden Forest! This unique Glamping experience is conveniently located only 12 minuets drive from the Warner bros Studio Tour & 40 minuets to central London via Chorleywood Metropolitan line. Hagrid's Hut sleeps five wizards - making it the perfect accommodation choice for families and friends. Soak under the stars in the leaky cauldron wood fired hot tub nestled in nature, MAGIC.

Luxury 2 bedroom cottage
Luxury Cottage at Hayley Green A charming, character-filled retreat for up to 4 guests in a peaceful semi-rural setting. Designed for comfort and relaxation, it’s ideal for couples, families, or friends. Enjoy a well-stocked library if you prefer to stay in. Perfectly located: 6 mins to Lapland Ascot 9 mins to Legoland 11 mins to Ascot 16 mins to Windsor & Wentworth 30 mins to Henley-on-Thames Under 1 hour by train to London via nearby Bracknell station

Unique Dome | Glamping | Hot Tub | Surrey | Adults
Olive Pod is the ultimate cosy, private and picturesque geo dome retreat. Set on a fruit farm in Surrey, in its own secluded field behind tall fir trees, with no other pods or tents nearby. A firm favourite adults-only escape for proposals, anniversaries, birthdays and honeymoons - we can also decorate for your arrival ✨ The perfect place to unwind and recharge in a peaceful natural setting. Ideal for couples or friends. No infants, children or pets.

Cheerful modern apt central Maidenhead, parking
Quiet location with free driveway parking, excellent road/rail links to London. On a tree lined street, 7 minutes walk from the Town Centre and Railway Station (London or Oxford 1hr max) The private space includes 2 double bedrooms, a large bathroom, en-suite shower room, a well equipped kitchenette and a relaxing lounge area Maidenhead Town Centre is being transformed with new restaurants, bars, coffee shops, and a new Leisure Centre 20 mins walk

Romantic Spring Glamping w/ Hot Tub & fire pit
Escape to this luxury countryside retreat, perfect for couples or families, just 40 minutes from Central London. Sleeping up to four guests, this private farm hideaway blends comfort and style with peaceful surroundings. relax in your own hot tub under the stars, cosy up by the fire pit, or enjoy a slow morning in the roll-top bath - the perfect setting to unwind and reconnect.
Popular amenities for Maidenhead holiday rentals
Other great holiday rentals in Maidenhead

The Green Views Work Contractors, Family, Travels

Racecourse Marina Lodge | Hot tub | Parking | EV

Private Garden Annex with Own Entrance

Spacious Sunny Apartment

1 bed flat, Maidenhead town centre, with parking.

Secluded Mansion Oasis - Charming Private Retreat

Spacious, Family Home - With Parking & Garden

Swallows Sanctuary • Lakeside Hut • Sauna, Hot Tub
When is the best time to visit Maidenhead?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $145 SGD | $152 SGD | $143 SGD | $158 SGD | $149 SGD | $154 SGD | $172 SGD | $166 SGD | $152 SGD | $150 SGD | $141 SGD | $144 SGD |
| Avg. temp | 6°C | 6°C | 8°C | 11°C | 14°C | 17°C | 19°C | 19°C | 16°C | 12°C | 8°C | 6°C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Maidenhead?
Maidenhead has more than 130 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Maidenhead?
Experience the best of Maidenhead with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Maidenhead?
Four-legged friends are welcome in Maidenhead. Choose from more than 60 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Maidenhead?
Yes! Work meets play with ease at over 130 vacation rentals in Maidenhead featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Maidenhead vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Maidenhead, available on Airbnb. Make a splash and soak up the sun in style!
Where should I stay in Maidenhead?
Make yourself at home in Maidenhead by choosing from our most frequently booked neighborhoods. We have over 680 vacation rentals in Maidenhead, over 1,700 vacation rentals in Taplow, and over 140 vacation rentals in Bray.
Do house rentals in Maidenhead have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Maidenhead. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Maidenhead have a kitchen?
Absolutely! We offer over 70 apartment rentals with a kitchen in Maidenhead. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Maidenhead have wifi?
Absolutely! We offer over 150 house rentals with wifi in Maidenhead. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Maidenhead have free parking?
Absolutely! We offer over 130 house rentals with free parking in Maidenhead. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Maidenhead

Total holiday rentals
Explore 310 holiday rentals in Maidenhead

Nightly prices starting at
Maidenhead holiday rentals start at $25 SGD per night before taxes and fees

Verified guest reviews
Over 9,770 verified reviews to help you choose

Family-friendly holiday rentals
130 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
130 properties have a dedicated workspace

Wifi availability
300 of Maidenhead holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Maidenhead rentals

4.7 Average rating
Maidenhead stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
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- South Downs National Park
- Paddington
- British Museum
- Covent Garden
- St Pancras International
- Hampstead Heath
- London Bridge
- Buckingham Palace
- Wembley Stadium
- Kings Cross
- Big Ben
- The O2
- Tower Bridge
- Marble Arch
- Tottenham Court Road
- Natural History Museum
- Trafalgar Square
- Piccadilly Theatre
- ExCeL London
- Emirates Stadium
- Battersea Power Station (disused)
- Royal Albert Hall
- Russell Square
- Olympia Events




