Holiday rentals in Maidenhead
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Top-rated holiday rentals in Maidenhead
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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!
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
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.
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.
Family & Contractor Friendly sleeps 8 Maidenhead
Our beautiful 3 Bed Townhouse that sleeps 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 home
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 !
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.
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.
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.
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.
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
Popular amenities for Maidenhead holiday rentals
Other great holiday rentals in Maidenhead
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1 bed flat, Maidenhead town centre, with parking.
Brayfields landmark luxury development
Maidenhead Imperial Court - 1 Bedroom Apartment
Sleeps 4 Maidenhead Windsor Ascot Legoland
When is the best time to visit Maidenhead?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $146 SGD | $138 SGD | $137 SGD | $160 SGD | $151 SGD | $157 SGD | $175 SGD | $168 SGD | $154 SGD | $153 SGD | $144 SGD | $146 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
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
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