Vacation rentals in Maidenhead

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Top-rated vacation rentals in Maidenhead

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Guest favorite
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, 34 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 favorite
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.

Top guest favorite
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, 129 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 favorite
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, 145 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 favorite
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, 109 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 favorite
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, 445 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 favorite
A bright studio space features a spacious bed with crisp white linen, set against a backdrop of exposed wooden beams. A comfortable sofa is nearby, and sliding glass doors offer views of the garden, enhancing the feeling of openness and light.
Guesthouse in Cookham
4.89 out of 5 average rating, 556 reviews

Riverside Boathouse

A warm and cosy studio style converted boat house on the edge of the River Thames in Cookham, Berkshire. Separate from the main house, the double glazed studio boathouse with en-suite, decorated beautifully. Egyptian cotton linen and nice towels. Relax with views of the river. Blackout blinds, kitchen, en-suite shower room, fridge, double glazing, heating, TV, WIFI, laptop area, outdoor seating/picnic blanket, umbrellas, off road parking, boat mooring, EV Charging Point (fee applies).

Top guest favorite
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, 309 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 favorite
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, 198 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 favorite
The exterior of the house is partially obscured by lush greenery, showcasing a combination of natural textures. A covered entrance leads into the living area, with a small wooden bench placed outside. A dog rests peacefully on the doorstep, complementing the serene garden setting.
Guesthouse in Berkshire
4.94 out of 5 average rating, 51 reviews

Branch House

Set in a secluded garden plot, Branch House is a place of rest and relaxation and is just minutes walk from the historic Thames Path and the futuristic Elizabeth Line. An ideal base from which to explore the quintessentially British towns of Windsor, Bray, Eton, Cookham, Marlow and Henley as well as the picturesque landscapes of the Chiltern Hills and the Thames Valley. Suitable for 2 adults and a child.

Superhost
Apartment in Berkshire
4.8 out of 5 average rating, 15 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 favorite
Condo in Central Windsor
4.93 out of 5 average rating, 46 reviews

Spacious 1-Bed w/ Double Height Ceiling

Experience comfort and charm and at this stylish one-bedroom apartment, just a 3-minute walk from the Windsor Castle. This brand-new, purpose-built, serviced apartment is nestled inside a locally listed Georgian property in the heart of Windsor with an abundance of pubs, bars, restaurants, bakeries and shops at your doorstep.

Popular amenities for Maidenhead vacation rentals

When is the best time to visit Maidenhead?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$23,850 GYDG$24,896 GYDG$23,431 GYDG$25,942 GYDG$24,477 GYDG$25,314 GYDG$28,243 GYDG$27,197 GYDG$24,896 GYDG$24,896 GYDG$23,850 GYDG$27,197 GYD
Avg. temp6°C6°C8°C11°C14°C17°C19°C19°C16°C12°C8°C6°C

Frequently Asked Questions

  • Do condo rentals in Maidenhead have a kitchen?

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

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

    Experience the best of Maidenhead with our apartment rentals, starting at about $20 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 660 vacation rentals in Maidenhead, over 1,700 vacation rentals in Taplow, and over 150 vacation rentals in Bray.

  • Do apartment rentals in Maidenhead have wifi?

    Absolutely! We offer over 70 apartment 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 Apartment Rentals in Maidenhead?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 70 homes with wifi, over 40 homes with free parking, over 70 homes with a kitchen, 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 apartment rentals in Maidenhead?

    Four-legged friends are welcome in Maidenhead. Choose from more than 10 apartment 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 vacation rentals in Maidenhead

  • Total vacation rentals

    Explore 290 vacation rentals in Maidenhead

  • Nightly prices starting at

    Maidenhead vacation rentals start at G$4,184 GYD per night before taxes and fees

  • Verified guest reviews

    Over 9,280 verified reviews to help you choose

  • Family-friendly vacation rentals

    120 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 70 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    130 properties have a dedicated workspace

  • Wi-Fi availability

    290 of Maidenhead vacation 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

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  5. Maidenhead