Vacation rentals in Maidenhead

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Top-rated vacation rentals in Maidenhead

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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 Maidenhead
4.97 out of 5 average rating, 258 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, 139 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
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 Taplow
4.82 out of 5 average rating, 786 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 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, 152 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
4.85 out of 5 average rating, 114 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, 456 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 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, 428 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 favorite
A spacious living area features a gray sofa adorned with decorative pillows, a sleek TV unit with a flat-screen television, and ambient lighting. A contemporary armchair in green adds a pop of color, while soft carpeting enhances comfort.
Condo in Marlow
4.96 out of 5 average rating, 264 reviews

Marlow F8 Penthouse 1 bed apartment WiFi & Parking

Stunning penthouse, 1 bed apartment in a central Marlow Location, free on-site parking and Juliet balcony. A full brand new kitchen, with all appliances, coffee machine, free high-speed WIFI, TV's in the living room and bedroom, with fire sticks. Dedicated work and fitness area with spinning bike, weights. Extra bed charged at £35.00, this is a foldout camp bed suitable for a child up to 12 years only. We require at least 24 hours notice for the extra bed.

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, 324 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 Maidenhead
4.96 out of 5 average rating, 211 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 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, 667 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.

Top guest favorite
A modern living area features a spacious sectional sofa arranged around a coffee table. Soft lighting is provided by hanging bulbs, while large windows allow natural light to fill the space. Decorative plants and a television complete the inviting atmosphere.
Barn in Bray
4.98 out of 5 average rating, 145 reviews

Oak Bray Coach House

Oak Bray Coach House is a new development which is located within the amazing grounds of the Oak Bray Manor estate , Enjoy the sounds of nature and experience amazing 360 views of the countryside when you stay in this unique place. 10 minutes away from Royal Ascot , and 20 mins via train to London

Popular amenities for Maidenhead vacation rentals

When is the best time to visit Maidenhead?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR1,925 ZARR2,009 ZARR1,891 ZARR2,093 ZARR1,975 ZARR2,043 ZARR2,279 ZARR2,195 ZARR2,009 ZARR1,992 ZARR1,874 ZARR1,908 ZAR
Avg. temp6°C6°C8°C11°C14°C17°C19°C19°C16°C12°C8°C6°C

Frequently Asked Questions

  • 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.

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

    Experience the best of Maidenhead with our condo rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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 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 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!

  • Where should I stay in Maidenhead?

    Make yourself at home in Maidenhead by choosing from our most frequently booked neighborhoods. We have over 670 vacation rentals in Maidenhead, over 1,700 vacation rentals in Taplow, and over 150 vacation rentals in Bray.

  • Do house rentals in Maidenhead have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Maidenhead. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Maidenhead have a kitchen?

    Absolutely! We offer over 10 condo rentals with a kitchen in Maidenhead. Enjoy a tailored experience with all the comforts you desire.

  • 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.

  • Do house rentals in Maidenhead have free parking?

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

Quick stats about vacation rentals in Maidenhead

  • Total vacation rentals

    Explore 300 vacation rentals in Maidenhead

  • Nightly prices starting at

    Maidenhead vacation rentals start at R338 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 9,770 verified reviews to help you choose

  • Family-friendly vacation rentals

    120 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    120 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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  2. United Kingdom
  3. England
  4. Berkshire
  5. Maidenhead