
Holiday rentals in Maidenhead
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Top-rated holiday rentals in Maidenhead
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Tree House - Hot Tub on balcony
Our rustic Glamping Treehouse stands 5m above the ground, which is accessible via an exciting seven-meter long suspension bridge. Boasting a warm themed interior, the Treehouse offers breathtaking views over the Chess Valley, which can be seen from the balcony and through the large panoramic window. Features include a spacious king-size double bed, en-suite toilet and basin facility. The outdoor balcony is home to a shower and hot tub, the perfect spot to relax amongst the surrounding treetops!

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

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.

Charming Cottage, dogs welcome, private garden .
A pretty cottage fully equipped for a comfortable holiday/ stay! Set back from the road, a peaceful haven. Private garden & parking. Easy walk to all local amenities & The River Thames. Great pubs &Michelin Star restaurants locally. The Chiltern Way offers a stunning path to all cyclists & walkers. Gorgeous old Towns of Windsor ( Legoland& Castle) Henley( Regatta & Festival)& Marlow (Tom Kerridge) , Cliveden, The Stanley Spencer Gallery,Train -London Paddington. M4 M40, Bicester Village .

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

Luxury self-contained Annexe with balcony Jacuzzi
Luxury self-contained annexe on the edge of the Chilterns, situated in the peaceful countryside which can be enjoyed from the hot tub, yet only 5 mins to the M40, 15 mins to Oxford Park & Ride & 15 mins to the station with trains to London taking 45 mins. It is the perfect place to relax with cosy lounge, wood burning stove, bespoke kitchen & underfloor heating. Upstairs features a super-king sized bed, seating area, luxury wet-room with underfloor heating, balcony and Jacuzzi.

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

The Ultimate Couples Retreat | 30 Mins from London
This countryside retreat is the perfect romantic escape, just a 35 minute taxi/train ride minutes from London. Unwind in your private luxury hot tub, sip on a complimentary bottle Champagne under the stars, and wake up to breathtaking views of rolling fields and wildlife. Our handcrafted shepherd’s hut blends rustic charm with modern comfort, offering a king-sized stargazing bed, a cozy fire-lit deck, and a luxury bathroom, all set in a peaceful meadow.

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

Beautiful self catering 2 bed Cottage
This beautifully restored Wheelwrights has been transformed into a contemporary 2 bedroom, (one kingsize bed. One twin beds) 2 bathroom cottage with all the luxuries of a modern home, and yet maintaining its original oak beams, vaulted ceilings and light gallery. This is a wonderful venue for couples, friends and families.
Popular amenities for Maidenhead holiday rentals
Other great holiday rentals in Maidenhead

The Green Views Work Contractors, Family, Travels

Private Garden Annex with Own Entrance

1 bed flat, Maidenhead town centre, with parking.

Branch House

Sleeps 4 Maidenhead Windsor Ascot Legoland

Charming Annexe in Maidenhead

Swedish cottage in Cookham Dean, 5 min to Marlow

Spacious, level, luxury home with log burner
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 apartment rentals in Maidenhead?
Maidenhead has more than 30 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in condo rentals in Maidenhead?
Experience the best of Maidenhead with our condo rentals, starting at about $40 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 apartment rentals in Maidenhead?
Four-legged friends are welcome in Maidenhead. Choose from more than 10 apartment rentals for guests traveling with pets.
Are there apartment rentals with a dedicated workspace in Maidenhead?
Yes! Work meets play with ease at over 10 apartment 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 apartment rentals in Maidenhead have wifi?
Absolutely! We offer over 70 apartment 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 300 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
120 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
120 properties have a dedicated workspace

Wifi availability
290 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
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- South Downs National Park
- Paddington
- British Museum
- Covent Garden
- St Pancras International
- Hampstead Heath
- London Bridge
- Buckingham Palace
- Big Ben
- Kings Cross
- Tower Bridge
- Wembley Stadium
- The O2
- 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




