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Vacation rentals in Maidenhead

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Top-rated vacation rentals in Maidenhead

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

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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
4.9 out of 5 average rating, 31 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, 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 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
4.93 out of 5 average rating, 120 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, 137 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
4.86 out of 5 average rating, 104 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 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, 438 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

Top guest favorite
A detached house with a brick and stucco exterior is visible. A paved driveway accommodates two vehicles, including a dark sedan and a blue SUV. Landscaping features a short hedge and a gravel area, framed by blue skies and a few scattered clouds.
Guesthouse in Berkshire
4.98 out of 5 average rating, 147 reviews

Self-contained studio Wokingham

A self-contained newly build 20 m2 studio with separate entrance and parking. The studio is comprised of an en-suite bathroom, a super-king bed, a tall boy and a work desk. A kitchenette just next to the room with fridge freezer, microwave, kettle, toaster, coffee machine, washing machine and a tumble dryer. “The kitchenette doesn’t have a stove or an oven.” The studio is brand new and built to high standards. The studio is a 15 minutes walk to Wokingham train station and town centre.

Guest favorite
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
4.9 out of 5 average rating, 105 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.

Guest favorite
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, 411 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 !

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, 298 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

Top 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
4.97 out of 5 average rating, 193 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

Top guest favorite
A charming self-contained cottage is set within a lush private garden, characterized by brick exterior and a slate roof. A welcoming door leads to the entrance, framed by greenery and flowering plants, with a spacious lawn surrounding the building.
Cottage in Windsor and Maidenhead
4.96 out of 5 average rating, 813 reviews

The Old School House, Ascot, Berkshire

Beautiful small self-contained character cottage set within private garden, one mile from Ascot. Open plan studio room with sitting area, kitchenette and bedroom area; en suite shower room/WC. Perfect for 1-2 adult guests looking for a comfortable and relaxing place to stay, whether for business or pleasure. It is ideal for visitors to Ascot Races, Windsor, close to Heathrow and a lovely rural retreat less than one hour from central London.

Popular amenities for Maidenhead vacation rentals

When is the best time to visit Maidenhead?

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Avg. priceG$23,837 GYDG$24,882 GYDG$23,418 GYDG$25,928 GYDG$24,464 GYDG$25,300 GYDG$28,228 GYDG$27,182 GYDG$24,882 GYDG$24,882 GYDG$23,837 GYDG$27,182 GYD
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Frequently Asked Questions

  • 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!

  • 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.

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$4,182 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

  1. Airbnb
  2. United Kingdom
  3. England
  4. Berkshire
  5. Maidenhead