Cottage holiday rentals in Windsor and Maidenhead

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.

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

Beautiful oak barn in peaceful countryside setting

Delightful detached barn crafted from French oak in a peaceful private lane on a gated country estate. Luxuriously appointed with full facilities for a short break or longer stay. Many public footpaths close by and local shops are only a 10 minute stroll away. Gastro pubs, restaurants and independent shops within easy walking distance. A short drive from M25 (J11). Free EV charging point. Fast rail links to London from Woking. LGBTQ+ friendly. Friendly Spaniel and Siamese cat on site.

Newly refurbished luxury 2 bedroom cottage

Luxury cottage at Hayley Green that accommodates up to 4 people in a semi-rural setting. Full of character with 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, 16 minutes to Wentworth.We are close to Bracknell train station where you take a train to London under 1 hour.

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.

Relaxing home near Legoland, Ascot, LaplandUK

This cosy cottage is situated in Windlesham, a pretty village in the Surrey Heath borough. Situated between Chobham Common and Swinley Forest, it is on the doorstep to some fantastic country walking and cycling routes; not to mention the famous golf courses in the area. Ideal location to visit Legoland, Thorpe Park, Ascot racing and Windsor castle. Heathrow Airport is only 15 miles away. Windlesham is known for the Boxing Day pram race and also a location to amazing gastro pubs.

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.

Perfect Location Windsor Cottage + Parking Option

Welcome to your stay at our Lovely Central Windsor Cottage. The cottage is full of character with a mix of traditional and a modern cozy feel. Perfect for a staycation, for the whole family or a quick break in Windsor. A stone throws away from all of Windsors attractions: take a stroll around the corner past the Diamond Jubilee Water Fountains and find yourself in front of the River Thames. Take a peak out of the King Bedrooms window to see the Windsor Castle!

Saddlers Rest perfect for Legoland & LaplandUK

A cosy 1860s Victorian cottage located opposite Windsor Racecourse. Just under a 3-5 minute drive to Windsor Castle and 8-10 minutes to Legoland, with an easy train ride to London via the Elizabeth Line. Lapland UK is only 20 minutes away by car. Ideal for families visiting Legoland and Windsor Castle, couples looking for a getaway, or friends seeking a relaxing time. Perfect for race days or events at Windsor Racecourse, with Dorney Lake just 10-15 minutes away.