Vacation rentals in Windsor and Maidenhead

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.

4.88 out of 5 average rating, 25 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!

4.92 out of 5 average rating, 215 reviews

An open-plan living space features a wooden ceiling beam, creating a cozy ambiance. The kitchen is equipped with modern appliances, and a comfortable seating area is arranged with stylish chairs and a sofa, with natural light flowing in through the large windows.

Cottage in Winkfield Row

Unique Cottage, Beautiful Views, Ascot, Windsor

This is the perfect hideaway to retreat, unwind and escape from the pressures of life. The cottage is a newly refurbished, converted stable block, set in a unique location. Close to historic towns & villages including Ascot and Windsor with direct trains from London Waterloo and close to the M4, M25 & M3. A plethora of Michelin starred restaurants, wonderful walks in Windsor Great Park, Virginia Water & the neighbouring Chilterns await you! Ideally situated for visiting Lapland UK and Legoland.

A bright living area features two large sofas in green tones and a stylish glass coffee table. A dining table with four chairs is set for a meal, complemented by wall art and natural light from a window with curtains.

4.96 out of 5 average rating, 157 reviews

Apartment in Windsor

Newly refurbished apartment located 10 minutes walk from Windsor Castle and the town centre with all of its great shops, bars, restaurants and tourist attractions. Benefits from its own private entrance, double bedroom, wet room, kitchen and separate living room with 2 large sofas and dining area. Easy access to the M4 and only a 10 minute walk to the train station with direct links into London, it is ideally located for a business stay or as a base to explore Windsor and the surrounding area.

4.95 out of 5 average rating, 102 reviews

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

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 suite in White Waltham

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.

4.94 out of 5 average rating, 421 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

4.98 out of 5 average rating, 199 reviews

A cozy studio space is showcased, featuring a king-size bed with light bedding and decorative pillows. Natural light enters through large windows, illuminating the comfortable seating area with a patterned rug. A small bookshelf adorns the wall, adding a touch of warmth to the inviting atmosphere.

Apartment in Datchet

Stylish Studio-Walk to Windsor/Eton/Thames/Parking

Welcome to Crail Cottage in Datchet. Surrounded by beautiful greenery, there is plenty of wildlife and the River Thames is just behind the house. Take a walk to Windsor and Eton via the home park or the riverside. You can even walk to Eton through the school grounds from here. Our little studio is freshly decorated and welcomes you to stay. There is a new addition which is a King size bed with Hypnos mattress that will guarantee you a good night sleep. Perfect to relax after a busy day.

The image displays the majestic stone architecture of Windsor Castle, featuring tall towers and an arched entrance. A warm sunset casts a soft glow over the walls. Surrounding benches and lamp posts are visible, adding to the historic atmosphere of the scene.

5 out of 5 average rating, 39 reviews

Epic Location, Views & Private Terrace

Any more central and you'd be in the Castle! Watch the King's Guards march past from the Kitchen window of this newly renovated 15th century penthouse apartment. We have clear views of the Castle, the Round Tower and the Royal Church, St George's Chapel. Everything is on your doorstep: Shops, Cafes, Restaurants, the stunning Long Walk and the 5,000 acre Windsor Great Park full of deer and ancient Oaks. We have 2 train stations to Central London & Heathrow is a 17 min drive.

5 out of 5 average rating, 20 reviews

The living room features a leather sofa paired with a stylish chair, both positioned around a wooden coffee table. Large glass doors open to the private garden, while a flat-screen TV is mounted on a wooden accent wall, providing a cozy and modern atmosphere.

Guest suite in Windsor

Annexe near Windsor town and Bray

A beautiful, modern ground floor private annexe and garden. Fully self contained with private entrance and secure parking. Living room/ diner leading on to private garden area. Separate toilet. Kitchen with hob and built in oven with extractor fan. Microwave, kettle, toaster and fridge. Washing machine and tumble dryer. All crockery & cutlery provided. Double bedroom with king size bed and en-suite shower & toilet. Large Flat screen TV's in bedroom & lounge. Separate toilet.

A cozy living area features a large window with views of Windsor Castle and the bustling street below. Elegant curtains frame the window, while a textured wall covering adds character. A wooden coffee table and a green sofa invite relaxation, complemented by decorative accents.

4.92 out of 5 average rating, 37 reviews

Castle View: Lux Apartment, Spa!Walk to River/Pubs

If you are looking for a unique, luxury experience with prime views of Windsor Castle then look no further. We are located right in the heart of Windsor High St with unobstructed views of Windsor Castle. We pride ourselves on being a truly unique concept for accommodation and relaxation. As part of booking your stay with us (retreat package) you will receive one free 30 minute treatment in the spa located above the apartment.

5 out of 5 average rating, 10 reviews

A modern lodge is surrounded by a glass balustrade, offering a clear view of the outdoor terrace furnished with a dining table and chairs. The well-maintained lawn provides a vibrant green space, and large windows reflect the bright sky with scattered clouds.

Home in Berkshire

Racecourse Marina Lodge | Hot tub | Parking | EV

Live your high life on Windsor Racecourse Marina! Discover your dream get away with this beautifully designed luxury lodge located in a prestigious gated community. This property is perfect for a couple or a family looking to enjoy a relaxing luxurious lifestyle in tranquillity and peace. With amazing views over Windsor Racecourse and the boats moored on the marina, every moment here is a picture of calm elegance.

5 out of 5 average rating, 25 reviews

The open living space showcases a round wooden dining table with two chairs, accompanied by a comfortable sofa. Natural light floods in through large windows, illuminating the kitchen area equipped with modern appliances. Potted plants are visible outside the windows, enhancing the tranquil setting.

Condo in Central Windsor

Cosy 1-Bed w/ Private Outdoor Area

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.

4.98 out of 5 average rating, 127 reviews

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 Winkfield

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

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Windsor and Maidenhead vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Windsor and Maidenhead's top sights

Thorpe Park12 locals recommend

LEGOLAND® Windsor Resort187 locals recommend

Ascot Racecourse89 locals recommend

Other great vacation rentals in Windsor and Maidenhead

Private room in Windsor and Maidenhead

4.97 out of 5 average rating, 35 reviews

En-suite bedroom with free parking in Windsor

Private room in Buckinghamshire

A private room is shown with a wooden bed featuring a floral-patterned purple bedspread and matching pillows. Nightstands are placed on either side of the bed, and natural light enters through a window with patterned curtains, enhancing the room's brightness.

4.97 out of 5 average rating, 150 reviews

Private ensuite Room near Pinewood Studios

Private room in Windsor and Maidenhead

A bright room is presented with a wooden bed beside a chair featuring a colorful upholstery pattern. A large window allows natural light to fill the space, complemented by light curtains. A decorative rug lies on the wooden floor, enhancing the overall comfort.

4.88 out of 5 average rating, 58 reviews

Newly Refurbished Tidy Room in a Cosy Cottage

Private room in Wokingham

A cozy double room is equipped with a spacious bed, complemented by a plaid bedding set. Wall-mounted lamps provide focused lighting on either side of the bed. A mirror and artwork adorn the walls, while wooden nightstands offer additional storage.

4.89 out of 5 average rating, 225 reviews

Cosy Room with Private Shower in Town Centre

Private room in Berkshire

A single room is furnished with a neatly made bed topped with a yellow blanket and folded towels. A desk with a chair provides a workspace, and a mounted TV offers entertainment options. Natural light enters through a window, framed by a roller shade.

4.97 out of 5 average rating, 116 reviews

Doll House - Sunny home

4.92 out of 5 average rating, 145 reviews

Private room in Burnham

Next, double/family bedroom

Private room in Maidenhead

4.96 out of 5 average rating, 342 reviews

Ground floor room with own shower and kitchenette