Vacation rentals in Windsor and Maidenhead

4.98 out of 5 average rating, 276 reviews

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

Newly refurbished luxury 2 bedroom cottage

Luxury cottage at Hayley Green that accommodates up to 4 people. Newly refurbished in semi-rural setting. Full of character with all the amenities you need for a luxurious comfortable stay. The perfect relaxing getaway for couples, family and friends. The cottage is located 16 minutes to Windsor, 30 minutes to Henley on Thames, 11 minutes to Ascot, 9 minutes to Legoland, 6 minutes drive to Lapland Ascot.We are also close to Bracknell train station where you take a train to London under 1 hour.

4.92 out of 5 average rating, 216 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, 158 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

Superhost

A charming historic cottage stands surrounded by a spacious, manicured lawn, dotted with fallen leaves. The property features traditional black and white timber framing, complemented by a warm roof. Ample parking is available in front of the house, nestled among lush trees.

Cottage in Dorney

4.89 out of 5 average rating, 276 reviews

Nr Windsor- Unique Cottage Stay for upto 14 guests

ASK ABOUT ADDITIONAL WEEKDAY DISCOUNTS FOR MULTIPLE NIGHT STAYS. Dorney Cottage is a truly unique property, dating back to the early 16th Century. Atmospheric & historic, yet homely & cosy all at the same time. With its stunning 30 ft Great Hall, which is now its kitchen, it is ideal for family gatherings and group celebrations. Sorry, but no house parties or loud music is permitted at any time. • Sleeps up to 14 • Entire House • Ample free parking • Set in own private grounds

5 out of 5 average rating, 119 reviews

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

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 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

Cottage in Englefield Green

A cozy living area features a comfortable white sofa adorned with striped cushions. Natural light filters through two windows with shades, highlighting a wooden coffee table and side table displaying a small vase of flowers. A mirror reflects the space, adding depth.

5 out of 5 average rating, 350 reviews

2 Bedroom Luxury Cottage (Secure & Quiet)

This charming Cottage is located in the picturesque Village of Englefield Green. Just four miles from Windsor Castle, three miles from Wentworth Golf Course and six miles from Ascot Race Course. Heathrow Airport if just six miles away. 300 metres further down the lane is The Royal Air Force Memorial and below that, on National Trust grounds that skirts the River Thames is the Magna Carta Memorial. The Royal Holloway University is a ten minute stroll across the Village.

Cottage in Windsor and Maidenhead

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.

4.96 out of 5 average rating, 790 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.

Apartment in Windsor and Maidenhead

A self-contained studio features a spacious double bed dressed in neutral linens, accented by yellow pillows and a decorative cushion. The kitchenette with modern appliances is visible in the background, complemented by simple shelving and a well-placed pendant light.

4.96 out of 5 average rating, 360 reviews

Windsor Great * Snug * Private Annexe with Parking

*stylish private annexe with off street parking for one car. * self contained studio attached to our family home. * suitable for up to 2 people only. * ideal for both work travellers (key box ) and tourists. * approx 21 m2 *quiet, leafy "Boltons" area. * 15\20 mins stroll to town centre and Castle. * 10 mins stroll to Long Walk and Great Park. * 5 mins cycle to Windsor Great Park cycle path. * local shop and pub 5-10 mins walk.

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.

4.98 out of 5 average rating, 128 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

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Popular amenities for Windsor and Maidenhead vacation rentals

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Other great vacation rentals in Windsor and Maidenhead

Private room in Maidenhead

Sunlight filters through a large window, illuminating a cozy bedroom with striped bedding. Floral curtains frame the view of greenery outside. A wooden dresser stands nearby, topped with a vase of fresh flowers, adding a touch of color to the serene space.

4.83 out of 5 average rating, 572 reviews

Double bedroom in Riverside home

5 out of 5 average rating, 10 reviews

A pale green front door is set within a brick entryway, featuring three clear glass panels. A small window above the door allows for natural light. Adjacent to the door, a modern mailbox and a decorative light fixture enhance the inviting entrance.

Condo in Berkshire

The perfect stay in the heart of Windsor

5 out of 5 average rating, 6 reviews

The exterior of the historic townhouse is showcased, featuring a combination of brick and stone elements. Lush greenery surrounds the property, with a gravel driveway leading to the entrance. Large windows enhance the welcoming appearance, and carefully landscaped gardens provide an inviting feel.

Home in Buckinghamshire

Historic Luxury Townhouse in Marlow

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

An open-plan living area is featured, showcasing a mix of seating options, including two armchairs and a spacious sofa. A dining table is set for four, with natural light filtering through two large windows. Modern kitchen appliances complement the stylish decor.

4.93 out of 5 average rating, 28 reviews

Smart Living by Lawsons

4.89 out of 5 average rating, 447 reviews

A loft room is shown, featuring a spacious bed with floral bedding and a charming red chair beside the window. A light-toned sofa is positioned nearby, with neatly stacked towels on a storage trunk. The room is bright with natural light illuminating the cozy decor.

Private room in Cookham

Warm, spacious loft room in Cookham

The kitchen features stylish cabinetry in soft green tones with marble countertops. A dining table is set for two, and natural light fills the space through a window. Modern appliances are integrated into the design, complemented by decorative elements on the shelves.