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Holiday houses in Maidenhead

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Top-rated holiday rentals in Maidenhead

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

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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 Berkshire
4.91 out of 5 average rating, 32 reviews

Homey Modern 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
A spacious sleeping area is presented with a large bed dressed in crisp white linens and a navy throw. Soft lighting is provided by two lamps on side tables, while a window with slatted blinds offers natural light. A mirror and chair complete the inviting space.
Apartment in Windsor and Maidenhead
4.97 out of 5 average rating, 253 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
4.93 out of 5 average rating, 122 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, 140 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 charming cottage is framed by a well-tended garden featuring a thatched roof. Comfortable seating is arranged on a grassy area, accompanied by a small table. The entrance door is flanked by windows adorned with flower pots, creating a welcoming look.
Guesthouse in Cookham Dean
4.86 out of 5 average rating, 106 reviews

Charming Cottage, dogs welcome, private garden .

A pretty cottage fully equipped for a comfortable holiday/ stay! Set back from the road, a peaceful haven. Private garden & parking. Easy walk to all local amenities & The River Thames. Great pubs &Michelin Star restaurants locally. The Chiltern Way offers a stunning path to all cyclists & walkers. Gorgeous old Towns of Windsor ( Legoland& Castle) Henley( Regatta & Festival)& Marlow (Tom Kerridge) , Cliveden, The Stanley Spencer Gallery,Train -London Paddington. M4 M40, Bicester Village .

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, 440 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

Guest favourite
A spacious bed is adorned with a decorative black-and-white blanket and an array of decorative cushions. Two nightstands with lamps are positioned on either side, providing balanced lighting. Natural light enters through a window fitted with dark blinds.
Guest suite in Cookham
4.9 out of 5 average rating, 414 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 !

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 Windsor and Maidenhead
5 out of 5 average rating, 73 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
4.98 out of 5 average rating, 302 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

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 Berkshire
4.96 out of 5 average rating, 195 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

Superhost
Apartment in Berkshire
4.73 out of 5 average rating, 11 reviews

Entire Flat: 1 Bedroom

The flat is a 10 min walk from Maidenhead Town Centre and 15-20 min walk to Maidenhead station. Please note access to the flat is up a flight of stairs There is designated off street parking for one car, but also free street parking. Inside you will find a fully equipped kitchen perfect for an over night stop or week long stay.

Guest favourite
A spacious two-story house is set within well-maintained gardens, featuring a combination of white stucco and wooden accents. Gravel leads to the front entrance, showcasing large windows that offer natural light and a welcoming appearance.
Home in Maidenhead
4.91 out of 5 average rating, 54 reviews

Private Annex Nicely Located

Self contained annex with own access, private kitchen and private bathroom. Set within lovely grounds on a quiet road. The house is very close to the M4, Windsor (10 mins), Ascot (15 mins) and Maidenhead (5 mins). Great space, easy drive to Windsor to see Royal wedding, for holidays and work I have 3 friendly dogs.

Popular amenities for Maidenhead holiday rentals

When is the best time to visit Maidenhead?

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Avg. price$174 AUD$182 AUD$171 AUD$190 AUD$179 AUD$185 AUD$207 AUD$199 AUD$182 AUD$182 AUD$174 AUD$199 AUD
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Frequently Asked Questions

  • Do house rentals in Maidenhead have a kitchen?

    Absolutely! We offer over 130 house rentals with a kitchen in Maidenhead. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in condo rentals in Maidenhead?

    Experience the best of Maidenhead with our condo rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Where should I stay in Maidenhead?

    Make yourself at home in Maidenhead by choosing from our most frequently booked neighborhoods. We have over 1,700 vacation rentals in Taplow, over 660 vacation rentals in Maidenhead, and over 150 vacation rentals in Bray.

  • Do condo rentals in Maidenhead have wifi?

    Absolutely! We offer over 20 condo rentals with wifi in Maidenhead. Enjoy a tailored experience with all the comforts you desire.

  • Are there condo rentals with a dedicated workspace in Maidenhead?

    Yes! Work meets play with ease at over 10 condo rentals in Maidenhead featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly apartment rentals in Maidenhead?

    Maidenhead has more than 30 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for Condo Rentals in Maidenhead?

    Enhance your stay in our Condo Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Maidenhead have free parking?

    Absolutely! We offer over 120 house rentals with free parking in Maidenhead. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly house rentals in Maidenhead?

    Four-legged friends are welcome in Maidenhead. Choose from more than 40 house rentals for guests traveling with pets.

  • Are there Maidenhead vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Maidenhead, available on Airbnb. Make a splash and soak up the sun in style!

Quick stats about holiday rentals in Maidenhead

  • Total holiday rentals

    Explore 290 holiday rentals in Maidenhead

  • Nightly prices starting at

    Maidenhead holiday rentals start at $31 AUD per night before taxes and fees

  • Verified guest reviews

    Over 9,280 verified reviews to help you choose

  • Family-friendly holiday rentals

    120 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 70 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

    290 of Maidenhead holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi 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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  2. United Kingdom
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  5. Maidenhead