Vacation rentals in Maidenhead

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Top-rated vacation rentals in Maidenhead

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The outdoor dining area features a table with four chairs under a green umbrella. Potted plants frame the space, and the background showcases large glass doors leading into the bungalow. Bright greenery and clear skies enhance the comfortable setting.
Bungalow in Amersham
4.86 out of 5 average rating, 234 reviews

Stunning Chiltern Views from Old Amersham Bungalow

NEW BUNGALOW Kyteway is a self-contained detached studio between the historic town of Old Amersham and the rolling Chiltern Hills. Offering fully equipped kitchen, spacious shower room, double bed in sleeping area, dining table, storage, and sofa bed. BEAUTIFUL VIEWS from private dining patio & separate sun terrace. Short walk to historic old town and easy access to new town (inc station to London) on foot, by car, or local bus. Adjacent to countryside footpaths. Unrestricted on-street parking.

Top guest favorite
The welcoming living area features a spacious gray sofa adorned with colorful cushions. A patterned area rug lies beneath the seating, which is accompanied by a stylish dining table. An open entryway leads to the kitchen, with abundant natural light streaming in from the garden.
Home in Marlow
5 out of 5 average rating, 127 reviews

Magical Marlow town centre

Wing Cottage is a charming period terraced cottage with log burner in the heart of Marlow. It has been stylishly refurbished and has its own secluded courtyard garden. 5 minutes walk from High St shops with Everyman Cinema, Tom Kerridge’s Michelin* Hand &Flowers & The Coach, plus Marlow Ivy Garden, Côte Brasserie, Piccolino, The Compleat Angler and several historic pubs. The Park and Thames Path river walk are 10 minutes walk. Nearby bus stops serve neighbouring Henley-on-Thames (8 miles away).

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

Guest favorite
A serene bedroom features vaulted ceilings with exposed beams and a large window offering views of greenery. The ornate bed is adorned with soft linens and decorative pillows. A vintage dresser with intricate details complements the space alongside a delicate chandelier.
Loft in Cookham
4.8 out of 5 average rating, 166 reviews

Luxury Apartment, The Barn, Cookham

The Barn is tucked away in a private courtyard set back on a picturesque and quiet lane that leads towards the village high street. Steeped in history and oozing character, it dates back to the 18th century. Vaulted ceilings and old beams frame the bedrooms which are furnished with an ornate bed/sofa bed/Egyptian cotton bed linen in a combination of dusky pinks/greys all in a shabby chic style. Chandeliers, silk bedspread, Farrow & Ball paint and Bamford Botanical sustainably made toiletries.

Guest favorite
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, 787 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, 153 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
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, 111 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 rustic barn-style exterior features a mix of brick and timber. The building is complemented by a wooden deck with several white metal chairs arranged around a table, surrounded by greenery and a wooden fence. Two dormer windows are visible on the roof.
Condo in Dorney
4.94 out of 5 average rating, 202 reviews

Gardener's Bothy loft apartment, peaceful location

Loft apartment, Gardeners Bothy, completely newly refurbished, in converted barn in unique rural location. Minutes walk from the Thames towpath and Dorney Rowing lake. 10 minutes drive to the M4, close to Windsor town centre and handy for Slough Trading Estate, difficult to believe this is all so close to this unique and peaceful location overlooking fields and Dorney Common. Lovely place for walkers and great base for many local attractions. Ideal spot to work or just relax.

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, 265 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

Popular amenities for Maidenhead vacation rentals

When is the best time to visit Maidenhead?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR1,903 ZARR1,986 ZARR1,869 ZARR2,070 ZARR1,953 ZARR2,020 ZARR2,253 ZARR2,170 ZARR1,986 ZARR1,969 ZARR1,853 ZARR1,886 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 R334 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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