Holiday rentals in Maidenhead

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Top-rated holiday rentals in Maidenhead

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Guest favourite
An outdoor hot tub is situated on a wooden deck, surrounded by lush greenery. A seating area with a light-colored chair offers a comfortable spot to relax. Large sliding glass doors lead into the retreat, allowing for seamless indoor-outdoor access.
Shepherd’s hut in Chessington
4.99 out of 5 average rating, 187 reviews

Lavish Retreat & Champagne 30mins Taxi from London

The Little Touch of Grey, provides an electric ambiance and the perfect setting for the elite of mind, who wants to reward both themselves and their partner. We are proud to share the latest addition to our portfolio with those who appreciate of all things bespoke. Included are; a complimentary bottle of Champagne, indoor & outdoor Jacuzzi, underfloor heating, sound system and salacious yet tasteful surprises throughout. For special occasions, use our secret compartment to add to your surprise.

Top guest favourite
Flat in Maidenhead
4.97 out of 5 average rating, 262 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, 152 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
A spacious living area is furnished with a large pink sectional sofa, complemented by a cozy throw. A round dining table for four and a kitchen area featuring modern appliances are visible. Natural light enters through multiple windows, enhancing the inviting ambiance.
Flat in Marlow
4.95 out of 5 average rating, 127 reviews

Marlow F7-Central-1 Bed Penthouse Wi-Fi & Parking

Stunning Second Floor Apartment, 1 bed apartment in a central Marlow Location, free on-site parking and private balcony. A full brand new kitchen, with all appliances, coffee machine, free high-speed WIFI, TV in the living room , with fire stick. Dedicated work and fitness area with spinning bike, weights. Extra bed charged at £35.00, this is a foldout armchair bed suitable for a children and small adults please note this is only a temporary bed. 24 hours notice required if this is needed.

Superhost
A serene bedroom features vaulted ceilings with exposed beams and a large window offering views of greenery. The ornate bed is adorned with soft linens and decorative pillows. A vintage dresser with intricate details complements the space alongside a delicate chandelier.
Loft in Cookham
4.79 out of 5 average rating, 171 reviews

Luxury Apartment, The Barn, Cookham

The Barn is tucked away in a private courtyard set back on a picturesque and quiet lane that leads towards the village high street. Steeped in history and oozing character, it dates back to the 18th century. Vaulted ceilings and old beams frame the bedrooms which are furnished with an ornate bed/sofa bed/Egyptian cotton bed linen in a combination of dusky pinks/greys all in a shabby chic style. Chandeliers, silk bedspread, Farrow & Ball paint and Bamford Botanical sustainably made toiletries.

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, 167 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
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, 471 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

Top guest favourite
Guest suite in Cookham
4.9 out of 5 average rating, 436 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
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, 342 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, 230 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

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, 201 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 .

Top guest favourite
A charming self-contained cottage is set within a lush private garden, characterized by brick exterior and a slate roof. A welcoming door leads to the entrance, framed by greenery and flowering plants, with a spacious lawn surrounding the building.
Cottage in Sunninghill
4.96 out of 5 average rating, 855 reviews

The Old School House, Ascot, Berkshire

Beautiful small self-contained character cottage set within private garden, one mile from Ascot. Open plan studio room with sitting area, kitchenette and bedroom area; en suite shower room/WC. Perfect for 1-2 adult guests looking for a comfortable and relaxing place to stay, whether for business or pleasure. It is ideal for visitors to Ascot Races, Windsor, close to Heathrow and a lovely rural retreat less than one hour from central 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