Holiday houses in Maidenhead

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Top-rated holiday rentals in Maidenhead

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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, 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.

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
4.83 out of 5 average rating, 780 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
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, 147 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
4.85 out of 5 average rating, 110 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
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, 448 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 property is shown, featuring a brick façade and a gravel driveway. A tall, spiky tree stands prominently in the foreground. A large window is visible on the side, allowing ample natural light into the space.
Place to stay in Cookham
4.91 out of 5 average rating, 106 reviews

Smart Loft annex in Cookham

Lovely first-floor loft annex on a quiet lane, just a few minutes’ walk from Cookham’s centre and its historic High Street with 7 pubs and restaurants. Bright and airy, the property is ideal for those seeking a village retreat: couples, small families, and business travellers. It features a double bedroom, lounge area with sofa bed (sleeps 1 adult), and separate bathroom. It has its own entrance and parking space within a secluded gated property. SkyTV with Sky Cinema/Kids/Sky/BT Sports.

Top 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, 419 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 modern kitchen area features sleek cabinetry and stainless steel appliances. A round dining table, surrounded by four black chairs, is positioned nearby. Natural light filters in through windows, enhancing the light wood flooring and neutral wall tones.
Cabin in Waltham Saint Lawrence
4.97 out of 5 average rating, 106 reviews

The Garden Cabin

Newly refurbish to a very high standard. The cabin is modern, light and airy and very peaceful. Accessed via a private pathway you enter your enclosed garden area, secure for dogs, with lawn, good sized decking with patio furniture. Based in the heart of the beautiful village of Waltham St Lawrence, The Cabin is a stones throw from the village pub and church. You are spoilt for choice for local walks and bike rides. Well worth a visit to this idyllic part of the country.

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, 313 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, 199 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 living area is highlighted by exposed wooden beams and a large window allowing natural light. Two soft white sofas are arranged around a wooden coffee table, with a flat-screen TV positioned on a black stand. A charming brick fireplace adds character to the room.
Apartment in Cookham
4.94 out of 5 average rating, 657 reviews

Old Butchers Wine Cellar 15th Century Apartment

Our restored 15th century apartment is in a unique position on Cookham High Street, located within 500 meters to 7 different restaurants and pubs and four Michelin Star restaurants within 3 miles. Situated above our beautiful wine shop with a pop up wine bar on Thursday, Friday and Saturday nights. We have very comfortable beds, 100% cotton sheets and towels. The perfect choice for couples, business travellers and families.

Guest favourite
A well-lit studio featuring a comfortable bed adorned with crisp linens and decorative pillows. A mounted television is positioned above the headboard, while a wardrobe provides ample storage. A cozy armchair adds a pop of color, completing the inviting ambiance of this modern space.
Apartment in Berkshire
4.89 out of 5 average rating, 131 reviews

Luxury studio apartment

STUDIO FLAT 25m2-PERFECT FOR CONTRACTORS/BUSINESS TRAVELERS Our studio flat offers a cosy living space, fully furnished with modern décor and all essential amenities in a single open space, making it ideal for both short- term or longer stays. Whether you are staying for a week or a year, you will enjoy the convenience of a combined living and sleeping area complemented by separate kitchen and bathroom.

Popular amenities for Maidenhead holiday rentals

When is the best time to visit Maidenhead?

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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 $30 AUD 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 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

    120 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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