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Holiday houses in Maidenhead

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Quick stats about holiday rentals in Maidenhead

  • Total holiday rentals

    Explore 320 holiday rentals in Maidenhead

  • Nightly prices starting at

    Maidenhead holiday rentals start at $34 NZD per night before taxes and fees

  • Verified guest reviews

    Over 10,050 verified reviews to help you choose

  • Family-friendly holiday rentals

    130 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    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

  • Wi-Fi availability

    300 of Maidenhead holiday rentals include Wi-Fi 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
The welcoming living area features a spacious gray sofa adorned with colorful cushions. A patterned area rug lies beneath the seating, which is accompanied by a stylish dining table. An open entryway leads to the kitchen, with abundant natural light streaming in from the garden.
Home in Marlow

Magical Marlow town centre

Wing Cottage is a charming period terraced cottage with log burner in the heart of Marlow. It has been stylishly refurbished and has its own secluded courtyard garden. 5 minutes walk from High St shops with Everyman Cinema, Tom Kerridge’s Michelin* Hand &Flowers & The Coach, plus Marlow Ivy Garden, Côte Brasserie, Piccolino, The Compleat Angler and several historic pubs. The Park and Thames Path river walk are 10 minutes walk. Nearby bus stops serve neighbouring Henley-on-Thames (8 miles away).

FamilyValueNearby

5.0 out of 5 average rating, 150 reviews
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

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

LocationFamilyCleanliness

4.95 out of 5 average rating, 165 reviews
Top Guest favourite
Apartment in Maidenhead

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.

FamilyLocationSleep quality

4.97 out of 5 average rating, 266 reviews
Top Guest favourite
The charming Victorian Lodge features a classic brick exterior with white trim, framed by lush greenery. Two inviting front windows and a central doorway are surrounded by decorative flower pots. A gravel pathway leads to the entrance, highlighted by an expansive tree nearby.
Cottage in Old Windsor

Gorgeous CountryCottage overlooking Windsor Castle

The Victorian Lodge (1876) is a charming & quintessentially English country cottage on a private estate once owned by King Henry 8th. It sits right beside Windsor Great Park, at the entrance of a long driveway to Little Dower House, where the owners of the Lodge live. The private gardens and stunning view at the Victorian Lodge provide the perfect setting for a small intimate wedding. Whilst the romantic gardens within the Little Dower House estate provide an ideal venue for larger weddings.

LocationFamilyLaundry

4.99 out of 5 average rating, 110 reviews
Superhost
A charming stand-alone annexe is nestled within a lush green garden, framed by neatly trimmed hedges. The building features a distinctive roof, skylights, and wooden beams, surrounded by mature trees and grassy areas inviting exploration and relaxation.
Guest suite in Maidenhead

Oak Barn - 1st Floor self contained Studio

Light and spacious apartment in a stand-alone annexe in the grounds of our house, 250m from the River Thames. Modern furniture, TV, wifi, full kitchen, washing machine, freezer. Great location for eating out and for access to countryside. Close to Windsor, Eton, Marlow, Cliveden National Trust and lovely river walks. 5 minutes from Maidenhead station. 10 minutes from The Fat Duck and the Waterside Inn. We are near a railway line. It doesn't bother us at all but you can hear the trains.

ValueFamilySleep quality

4.82 out of 5 average rating, 809 reviews
Top Guest favourite
Condo in Maidenhead

Friends & Families | Parking & EV | Station nearby

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

ValueLocationTV

5.0 out of 5 average rating, 83 reviews
Guest favourite
Townhouse in Maidenhead

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

FamilyLocationAmenities

4.88 out of 5 average rating, 16 reviews
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

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.

LocationFamilyBarbecue

5.0 out of 5 average rating, 79 reviews
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 Bracknell Forest

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

ValueFamilyHospitality

4.97 out of 5 average rating, 364 reviews
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.
Condo in Maidenhead

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

ValueLocationLong stay

4.96 out of 5 average rating, 248 reviews
Superhost
Home in Maidenhead

Spacious 4-Bed in Maidenhead | Parking | Sleeps 8

This modern four-bedroom retreat offers two en suite bedrooms, a family bathroom, a fully equipped kitchen, and spacious living areas that open onto a private garden, along with parking for up to two cars. Just a short walk from Maidenhead town centre, it’s ideal for families or groups looking for generous space, modern comforts, and a convenient, relaxed place to stay.

Air conditioningIndoor spacesCondition

5.0 out of 5 average rating, 3 reviews
Top Guest favourite
A bright open-plan seating area features a large grey settee adorned with yellow accent pillows. A small coffee table sits in front, complemented by a sleek cabinet and a wall-mounted TV. Bifold doors lead out to a private patio with garden views.
Home in Marlow

Home in Marlow

If you’re looking for a quiet central location (with the luxury of parking), in a spacious and stylish modern newly renovated extension then this is the place for you! Whether you're looking to relax and unwind or enjoy the many bars, restaurants and shops that Marlow has to offer, this is a great place to stay.

FamilyValueLayout

4.98 out of 5 average rating, 108 reviews

Popular amenities for Maidenhead holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Maidenhead's top sights

Cliveden - The National Trust

100 locals recommend

The Crown

29 locals recommend

Ray Mill Island

15 locals recommend

Other great holiday rentals in Maidenhead

Guest favourite
Home in Maidenhead

Spacious, Family Home - With Parking & Garden

FamilyLocationParking

4.86 out of 5 average rating, 14 reviews
Top Guest favourite
Tiny home in Maidenhead

Cosy Studio with own bathroom and kitchen

FamilyLocationParks

5.0 out of 5 average rating, 24 reviews
Guest favourite
A bright bedroom features a spacious bed layered with a textured white blanket and numerous neutral-toned pillows. Natural light flows through a large window dressed with simple curtains. Two bedside tables with decorative plants and art pieces enhance the welcoming ambiance of the room.
Apartment in Maidenhead

Homey Modern Stay in Maidenhead

ValueLocationCheck-in

4.9 out of 5 average rating, 40 reviews
Guest favourite
The exterior of the historic townhouse is showcased, featuring a combination of brick and stone elements. Lush greenery surrounds the property, with a gravel driveway leading to the entrance. Large windows enhance the welcoming appearance, and carefully landscaped gardens provide an inviting feel.
Townhouse in Marlow

Historic Luxury Townhouse in Marlow

LocationFamilyOutdoor spaces

4.97 out of 5 average rating, 61 reviews
Superhost
Home in Maidenhead

Family 6 Bed | Gated Parking, Sleeps 11, Bray

AmenitiesCleanlinessComfort

4.83 out of 5 average rating, 6 reviews
Top Guest favourite
Apartment in Bray

Apartment in Bray, secure parking & EV charge inc.

ValueFamilyKitchen

4.93 out of 5 average rating, 75 reviews
Superhost
A spacious garden features a well-maintained lawn shaded by several trees. A dining table is set with chairs under a green umbrella, while ornamental plants are placed in various pots nearby. The house is visible in the background, showcasing bi-fold doors that open to the interior.
Home in Maidenhead

Bright & Spacious Home 10 min from Elizabeth line

LocationFamilyAccess

4.79 out of 5 average rating, 193 reviews
Superhost
A sleeping area features a wooden bed with a floral-patterned duvet cover and four pillows arranged neatly. A bedside table with a lamp and a framed wall art piece is positioned above it. Light tones dominate the wood flooring, complemented by white walls and wardrobe.
Condo in Maidenhead

Thieves Garden Apartment

LocationValueLong stay

4.5 out of 5 average rating, 54 reviews

When is the best time to visit Maidenhead?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$192 NZD$182 NZD$180 NZD$209 NZD$205 NZD$215 NZD$229 NZD$221 NZD$202 NZD$200 NZD$188 NZD$192 NZD
Avg. temp6°C6°C8°C11°C14°C17°C19°C19°C16°C12°C8°C6°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.

Destinations to explore