Holiday rentals in Maidenhead

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Top-rated holiday rentals in Maidenhead

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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.
Flat in Berkshire
4.91 out of 5 average rating, 35 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
Flat in Windsor and Maidenhead
4.97 out of 5 average rating, 256 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
4.94 out of 5 average rating, 138 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

Superhost
Guest suite in Maidenhead
4.82 out of 5 average rating, 785 reviews

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.

Top guest favourite
Tiny home in Berkshire
4.98 out of 5 average rating, 60 reviews

Private Garden Annex with Own Entrance

You have driveway and roadside parking, your own private entrance and secluded garden. The fabulous open plan has fully fitted kitchen with integrated combi microwave oven, fridge/freezer, hob and instant hot water. The living area is welcoming with corner sofa, electric fire, smart tv and dining area overlooking your private garden. The bedroom is cosy and welcoming and the wetroom bathroom is just perfect. On a no through road, with two fab gastro pubs, a local café, butcher and more.

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, 150 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.
Guest house in Cookham Dean
4.85 out of 5 average rating, 112 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 .

Top guest favourite
Guest suite in White Waltham
4.94 out of 5 average rating, 455 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
The exterior of the house is framed by vibrant foliage, with climbing plants covering part of the brick walls. A pathway leads to a covered area with wooden seating. The lush, green lawn is bordered by potted plants, enhancing the tranquil garden setting.
Guest house in Berkshire
4.95 out of 5 average rating, 55 reviews

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.

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, 209 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 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
4.9 out of 5 average rating, 60 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.

Top guest favourite
A modern kitchen area features sleek gray cabinetry and a white countertop. A black sink with a faucet is complemented by an electric stove and kettle. Shelves above showcase decorative items, with plants adding a touch of greenery to the space. Natural light filters through the window.
Flat in Berkshire
4.97 out of 5 average rating, 88 reviews

Charming Annexe in Maidenhead

A calming and delightful self contained annexe with its own private entrance and patio. Other great facilities include shared use of a lovely garden and 24 hour use of our gym and fitness room. An ideal place to stay to explore the surrounding area, or as a base if you’re working or studying.

Popular amenities for Maidenhead holiday rentals

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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 150 vacation rentals in Bray, and over 670 vacation rentals in Maidenhead.

  • 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 house rentals with a dedicated workspace in Maidenhead?

    Yes! Work meets play with ease at over 60 house rentals in Maidenhead featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly house rentals in Maidenhead?

    Maidenhead has more than 70 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Enhance your stay in our House Rentals with the most popular amenities: over 120 homes with free parking, over 130 homes with a kitchen, over 140 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do apartment rentals in Maidenhead have free parking?

    Absolutely! We offer over 40 apartment 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 300 holiday rentals in Maidenhead

  • Nightly prices starting at

    Maidenhead holiday rentals start at $25 SGD per night before taxes and fees

  • Verified guest reviews

    Over 9,770 verified reviews to help you choose

  • Family-friendly holiday rentals

    120 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

    120 properties have a dedicated workspace

  • Wifi availability

    290 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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