Holiday rentals in Maidenhead

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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

Top-rated holiday rentals in Maidenhead

Guests agree: these stays are highly rated for location, cleanliness and more.

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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 Maidenhead
4.94 out of 5 average rating, 17 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
Flat in Maidenhead
4.97 out of 5 average rating, 264 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.

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
4.94 out of 5 average rating, 156 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
Apartment in Maidenhead
5 out of 5 average rating, 72 reviews

Friends & Families | Parking & EV | Station close

Top-floor apartment in a stunning Grade II Listed Arts & Crafts mansion in Maidenhead. Sleeps 6 across 3 bedrooms - ideal for families or groups of friends. Perfect base for Legoland (15 min drive), Windsor (20 min) and London via the Elizabeth Line (10 min walk to station). Also close to Lillibrooke Manor (wedding venue). Fully equipped kitchen, AC, free driveway parking for several cars, EV charger (payable via TAP app), washer/dryer and a selection of books and games for the kids.

Guest favourite
The exterior of the house is partially obscured by lush greenery, showcasing a combination of natural textures. A covered entrance leads into the living area, with a small wooden bench placed outside. A dog rests peacefully on the doorstep, complementing the serene garden setting.
Guest house in Maidenhead
4.95 out of 5 average rating, 56 reviews

Branch House

As a furniture maker, I spent five years designing and building this house by hand. Inspired by bird hides and nature reserves the space is designed around long windows overlooking the Marlow branch line - a green corridor where local wildlife can be observed. Cats, foxes, birds, badgers and deer are all common. The house is built from British grown Oak and Douglas Fir from a historic sawmill in the South Downs. The space is designed to a human scale using natural textures and materials.

Top guest favourite
The exterior view shows a contemporary cabin with wooden siding, surrounded by a well-maintained green garden. A large glass door opens to the interior, while a planter box with bamboo and other plants creates a tranquil atmosphere.
Cabin in Maidenhead
5 out of 5 average rating, 77 reviews

Charming Garden Cabin Retreat

Charming cabin, clean, quiet & cosy. Newly built and furnished. Bedroom, bathroom, living room. Kitchen has microwave, oven, hob & fridge/freezer, larder. TV includes Netflix & Prime. High speed Broadband. Quiet & private garden area with fire pit. Close to M4/M40 & Heathrow. Near Windsor, Marlow, Cookham & Henley. Ten minutes walk from the River Thames/Boulters Lock/Thames Path. Cliveden House & Bray Michelin starred restaurants close. For 2 guests maximum. Not suitable for children.

Top guest favourite
Tiny home in Maidenhead
5 out of 5 average rating, 16 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.

Top guest favourite
Home in Marlow
4.96 out of 5 average rating, 23 reviews

Luxury cottage 5 mins walk from Marlow High St

Beautiful one bedroom cottage just a short walk from Marlow town centre and its award-winning restaurants. Full of character with a large kitchen, lounge and bedroom that blend seamlessly with tasteful furnishings. From the moment you step through the door, you’ll feel the warmth and character of this much-loved home. Perfect for enjoying countryside walks, and vibrant Marlow life. A bedroom, a bathroom and parking. It's located just 200m from the famous Hand & Flowers restaurant.

Guest favourite
A spacious exterior view of the converted barn features large glass panels that allow natural light to flood the interior. A manicured lawn and planted pots are visible in the foreground, while the structure's brick façade adds character. The sunny sky emphasizes the inviting atmosphere.
Guest house in Maidenhead
4.8 out of 5 average rating, 41 reviews

Annex with Stunning Views

Beautiful views of Cliveden. Spacious double room with living area with large TV & Sofa. Access to a large garden. Easy parking and 10 minutes from Maidenhead train station. The main house is a converted barn and the connected annex is in the garden. We do have 4 dogs who are ever friendly. Fine to have well behaved dogs to stay! Microwave, fridge, sink included. There is not a full kitchen. Large bathroom with separate shower & double bath. Please do ask any questions

Top guest favourite
A bright living room features a comfortable grey sofa and a turquoise chaise lounge. Natural light filters through large windows with plantation shutters. A modern coffee table sits in the center, with a decorative item displayed. A working fireplace adds a cozy touch to the space.
Home in Maidenhead
5 out of 5 average rating, 77 reviews

Artists Victorian Semi

A charming Victorian semi on a quiet cul-de-sac with a beautifully landscaped garden where you’ll have two terraces, a comfy day bed, fire pit and gas BBQ to enjoy from May - September. Relax in the cosy living room with a working fire or in one of the two spacious double bedrooms. With Windsor, Marlow and Henley all only a 15 minute drive away or Maidenhead station a 25 minute walk with direct links to London, my home is situated in the perfect location.

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
4.97 out of 5 average rating, 347 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 Maidenhead
4.96 out of 5 average rating, 237 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

Popular amenities for Maidenhead holiday rentals

When is the best time to visit Maidenhead?

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Frequently Asked Questions

  • What are the best places to stay in Maidenhead?

    Stays around the town center provide convenient access to shops and dining, while neighborhoods near the riverside are frequently suggested for a peaceful atmosphere. Residential areas and nearby villages can also provide quieter surroundings.

  • What are the best things to do in Maidenhead with kids?

    Families often explore parks, riverside walks, or leisure centers with swimming pools and play areas. The Maidenhead Heritage Centre provides interactive exhibits that appeal to a range of ages.

  • What are some of the best things to do in Maidenhead?

    Explore riverside walks, discover the Maidenhead Heritage Centre, or visit historic sites like the nearby Maidenhead Bridge. Seasonal boat trips on the River Thames are also frequently suggested.

  • How is the weather in Maidenhead?

    Maidenhead has mild winters around 37–48°F (3–9°C) and summer highs near 75°F (24°C), with rainfall spread throughout the year. Light layers and a waterproof jacket are practical for most visits.

  • When is the best time to visit Maidenhead?

    Late spring to early autumn is often recommended for milder weather and a variety of outdoor events. In spring, local parks feature blossoms and riverside walks become especially popular.

  • What are the best places to visit in Maidenhead?

    Many enjoy the Maidenhead Heritage Centre for local history, walks by the River Thames, and the historic Maidenhead Bridge. The nearby Cliveden estate with its extensive gardens is also frequently suggested.

  • What are some hiking trails in Maidenhead?

    Maidenhead has riverside walking routes and woodland trails in nearby areas. The Thames Path, with scenic stretches along the river, is especially popular for leisurely hikes.

  • What are some family activities we can do in Maidenhead?

    Parks with play areas, riverside walks, and visits to the Maidenhead Heritage Centre are often enjoyed by families. Rowing or feeding ducks along the river can also be relaxing ways to spend time together.

  • What are some of the best day trip ideas from Maidenhead?

    Visitors frequently take day trips to historic Windsor, vibrant Reading, or the gardens at Cliveden. Country villages around Maidenhead and city attractions in London are also within reach for those seeking a mix of experiences.

  • Are there any pet friendly accommodations available in Maidenhead?

    A selection of accommodations in Maidenhead welcomes pets, especially in residential areas and near green spaces. Many rental hosts clearly indicate pet-friendly policies to help guests travel comfortably with animals.

  • What are some local tips for visiting Maidenhead?

    Exploring the riverside paths is a favorite local pastime, especially early in the day or during sunset. Many visitors enjoy sampling baked goods at independent cafés and browsing weekend markets for handmade items.

  • What is Maidenhead known for?

    Maidenhead is known for its riverside setting on the Thames, Victorian-era architecture, and historic bridges. The town has a longstanding reputation as a peaceful retreat with access to scenic green spaces.

  • What are the best hidden gems to explore in Maidenhead?

    Independent art galleries, tucked-away gardens, and local markets provide opportunities for unique finds in Maidenhead. Small bakeries and riverside viewpoints are also frequently discovered by visitors who wander beyond the main streets.

  • What are the best foods to try in Maidenhead?

    The area is known for locally baked pastries, classic English roasts, and seasonal dishes featuring produce from Berkshire farms. Riverside pubs often serve traditional pies and freshly prepared desserts.

  • What should I bring for a trip to Maidenhead?

    It is practical to pack layers for varying temperatures, a waterproof jacket, and comfortable shoes for riverside walks. Bringing a reusable water bottle and a camera comes in handy while exploring town cafes, markets, and green spaces.

  • What is the nightlife in Maidenhead like?

    Maidenhead has a variety of pubs, cozy bars, and casual venues with live music or themed nights, concentrated around the town center. Many visitors enjoy relaxed evenings with cocktails, craft beer, or live performances.

  • What are the most popular events or festivals in Maidenhead?

    Community festivals, regattas on the River Thames, and art fairs are among the most popular events throughout the year. Seasonal celebrations and food markets often draw both locals and visitors.

  • Are there family friendly vacation rentals in Maidenhead?

    Maidenhead has a variety of family-friendly rentals, with many homes and apartments providing extra space or child-focused amenities. Listings often highlight proximity to parks and ease of access for families.

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