Holiday rentals in Maidenhead

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Top-rated holiday rentals in Maidenhead

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Top guest favourite
A well-appointed bedroom features a spacious bed adorned with a textured white coverlet and several neutral-toned pillows. Natural light filters through large windows, highlighting the soft color palette. Two bedside tables with minimal decor complete the inviting look of the room.
Flat in Berkshire
4.93 out of 5 average rating, 14 reviews

Cosy & Homely Stay in Maidenhead

Welcome to my home! Wind down and relax in this stylish and charming space 🌆 Short walk to Maidenhead town centre’s shops, supermarkets, restaurants, bars and pubs 🚝 Short walk to train station with services to Central London in 20 min 🌲 31 acres of Braywick’s Nature Reserve Park around the corner Local to surrounding areas Bray, Windsor and Ascot. Short drive to attractions including Legoland and Thorpe park 🎡 This is my home so it’s fully functional, you also have your own parking space!

Top guest favourite
A spacious sleeping area is presented with a large bed dressed in crisp white linens and a navy throw. Soft lighting is provided by two lamps on side tables, while a window with slatted blinds offers natural light. A mirror and chair complete the inviting space.
Flat in Windsor and Maidenhead
4.97 out of 5 average rating, 261 reviews

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.

Top guest favourite
The charming exterior of a Victorian terraced home features a white door framed by climbing greenery. Flower boxes filled with pink and white blooms adorn the windows, while a small bench sits beneath a decorative wrought iron fence.
Cottage in Bray
4.95 out of 5 average rating, 148 reviews

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

Top guest favourite
The cottage's serene garden is shown, featuring a stone patio with a wooden dining set surrounded by greenery. Sunny skies illuminate the exterior of the cottage, with trees and shrubs providing privacy and a peaceful atmosphere.
Cottage in Bray
5 out of 5 average rating, 159 reviews

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.

Top guest favourite
A cozy sleeping area features a spacious bed with neutral bedding against a softly colored wall. A small armchair and a light-colored rug complement the wooden flooring. Wall-mounted shelves display framed images, and a small closet provides additional storage.
Guest suite in White Waltham
4.94 out of 5 average rating, 464 reviews

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

Guest favourite
A spacious bed is adorned with a decorative black-and-white blanket and an array of decorative cushions. Two nightstands with lamps are positioned on either side, providing balanced lighting. Natural light enters through a window fitted with dark blinds.
Guest suite in Cookham
4.9 out of 5 average rating, 429 reviews

Southwood Gardens annexe in Cookham

We are right on the edge of the beautiful village of Cookham. The accommodation is annexed to the main house and is accessed through a secured side-gate for total privacy. There is also free private parking on the front drive. The room is ideal for people who need to commute (1 hour by train to London, 25 minutes drive to Heathrow), or families who need to have additional accommodation for their loved ones to stay in the area. We very much look forward to welcoming you to Cookham soon !

Guest favourite
Tiny home in Windsor and Maidenhead
5 out of 5 average rating, 11 reviews

Cosy Studio with own bathroom and kitchen

In a quiet location, within 15 minutes walk of the train station and town centre, 25 minutes walk from the SMAE institute and Norden Farm Arts Centre and a short drive to Bray, Windsor, Cookham, Marlow and Henley. The studio has underfloor heating and is warm all year round. There is a patio where you can enjoy your morning coffee and a recently refitted kitchen with fridge, induction hob and combi oven. The Studio has its own entrance and free on-street parking is available nearby.

Guest favourite
Townhouse in Berkshire
5 out of 5 average rating, 8 reviews

Family & Contractor Friendly sleeps 8 Maidenhead

Our beautiful 3 Bed Townhouse that sleep 8 with 2.5 bathrooms. 6 minutes drive to Maidenhead Town Centre & train station (Elizabeth Line-24 min Paddington) 19 minutes drive to Windsor Castle 20 minutes drive to LegoLand Key Features: ? 3 bed townhouse ( Sleeps up to 8) ? Prime Location ? Free private parking for 2 cars ? Fast Wi-Fi & Smart TV ? Professionally cleaned with fresh linen provided ? Easy self-check-in & 24/7 guest support ? Fully equipped kitchen – cook meals at

Top guest favourite
The exterior of the modern annexe is showcased, featuring large glass doors that allow natural light to fill the interior. A spacious balcony is visible above, bordered by glass, and wooden furniture is arranged on the terrace, ideal for outdoor relaxation.
Home in Tetsworth
5 out of 5 average rating, 368 reviews

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.

Top guest favourite
A cozy sitting room is featured, showcasing a comfortable armchair and a large coffee table adorned with various books and decorative items. A warm fire burns in the fireplace, and built-in shelving lines one wall, filled with a diverse selection of books.
Cottage in Warfield
4.98 out of 5 average rating, 333 reviews

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

Top guest favourite
The entrance to the house features a covered porch framed by lush greenery and climbing plants. A pathway leads to the front door, which opens into a welcoming lobby. Stacked logs are visible beside the entrance, adding a rustic touch to the outdoor space.
Apartment in Berkshire
4.96 out of 5 average rating, 220 reviews

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

Top guest favourite
A modern living area features a spacious sectional sofa arranged around a coffee table. Soft lighting is provided by hanging bulbs, while large windows allow natural light to fill the space. Decorative plants and a television complete the inviting atmosphere.
Barn in Winkfield
4.98 out of 5 average rating, 146 reviews

Oak Bray Coach House

Oak Bray Coach House is a new development which is located within the amazing grounds of the Oak Bray Manor estate , Enjoy the sounds of nature and experience amazing 360 views of the countryside when you stay in this unique place. 10 minutes away from Royal Ascot , and 20 mins via train to London

Popular amenities for Maidenhead holiday rentals

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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 apartment rentals in Maidenhead?

    Experience the best of Maidenhead with our apartment rentals, starting at about $20 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 condo rentals in Maidenhead have a kitchen?

    Absolutely! We offer over 10 condo 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 condo rentals in Maidenhead have free parking?

    Absolutely! We offer over 10 condo 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 $26 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

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  2. United Kingdom
  3. England
  4. Berkshire
  5. Maidenhead