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, 15 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!

Superhost
A charming exterior view of the property reveals a combination of brick and white walls. A grassy area is framed by greenery, with a small table and chairs located just outside. Leafy plants and a shed provide a natural setting, while a gravel pathway leads to the entrance.
Apartment in Berkshire
4.85 out of 5 average rating, 13 reviews

Spacious Apartment with Parking near River Thames

A bright and cosy 1-bed flat in a quiet residential street, perfect for couples or professionals. Enjoy a light-filled lounge with Smart TV, a fully equipped kitchen with garden views, and a peaceful double bedroom with soft bedding. The modern bathroom includes a full bath and power shower. You’ll have private access, off-street parking, and use of the shared garden. Just minutes from Maidenhead town centre, and the River Thames. Great transport links. Ideal for work trips or weekend getaways.

Top guest favourite
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, 149 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.

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
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, 221 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 detached barn-style maisonette with a combination of brick and stone exterior stands in a landscaped setting. Large windows allow natural light to filter through, while a staircase leads to an upper terrace. Well-maintained lawns provide a green backdrop.
Cottage in GB
4.94 out of 5 average rating, 197 reviews

Luxurious Barn between Marlow & Henley

A luxurious 2 bedroom detached maisonette barn with garden, terrace and outstanding views over the Chiltern Hills.Situated in the picturesque village of Medemenham, 2 miles from Marlow and 5 miles from Henley-on-Thames. Located opposite Danesfield House Hotel and with stunning woodland walks accessible straight from the property and easy access to the River and Harleyford Golf Course . The property has 2 parking spaces, air conditioning ,wifi .

Guest favourite
Guest suite in White Waltham
4.97 out of 5 average rating, 326 reviews

A delightful oak-framed studio, own entrance.

Beautiful oak-framed studio apartment in the picturesque village of White Waltham. Spacious but cosy property with garden views. Conveniently located for Windsor, Henley, Marlow, M4. Bistro pub, The Beehive, in easy walking distance. Local walks. Great for a quick escape. Perfect for 1-2 guests.

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

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.

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

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