Cottage vacation rentals in Maidenhead

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Top-rated cottage rentals in Maidenhead

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Top guest favorite

Cottage in Warfield

4.98 out of 5 average rating, 268 reviews

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.

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Cottage in Englefield Green

4.88 out of 5 average rating, 184 reviews

Luxury 5* House Near Windsor Castle, Ascot, London

This Grade 11 listed Mews property was built in 1872 and offers contemporary, luxurious living space. Luxurious king size beds, beautiful bathrooms, abundant art and character; the properties look onto an ancient courtyard with fountain, secure behind private gates with parking. The location is exceptional. Windsor Great Park is a 10 min stroll away, and Windsor is 3 miles away, Wentworth Golf Club and Ascot are all within 6 miles. Central London is 35 minutes by train. Heathrow is 6 miles away.

Guest favorite

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

4.91 out of 5 average rating, 211 reviews

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.

Guest favorite

A spacious kitchen and dining area features rustic wooden beams and a large table surrounded by benches. A well-equipped kitchen counters along the wall include a stove and sink, while light streams in through large windows, highlighting the warm tones of the wooden flooring.

Cottage in Crowmarsh Gifford

4.96 out of 5 average rating, 353 reviews

Gardeners’ Cottage (Georgian stable conversion)

An entirely self contained cottage, recently converted from a Georgian stable and gardeners’ lodge. While adjacent to the owners property it is entirely separate, with its own secure parking and EV charger. Located in a small village, with two pubs and charming village shop on doorstep. Market town of Wallingford (setting for “Midsomer Murders”) is short walk, many amenities including boat rides on the River Thames an outdoor heated pool (summer), great restaurants and shops including Waitrose.

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Cottage in Dorney

4.89 out of 5 average rating, 274 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

Top guest favorite

Cottage in Sarratt

5 out of 5 average rating, 238 reviews

Crestyl Cottage riverside barn for 2 with hot tub

Crestyl Cottage is a delightful self contained country cottage in Sarratt - providing the perfect place to relax, walk, cycle, birdwatch and fish for carp in our small private lake. We provide high end accommodation for 2 adults in an area which has plenty to offer in the heart of the stunning Chess Valley. Crestyl Cottage is a conversion of a redundant barn, originally used for watercress seed drying which has been converted into self catering holiday accommodation with wood fired hot tub.

Top guest favorite

A bright and inviting open-plan living and dining area features large glass doors leading to the outdoor space. A dining table with wooden chairs is positioned next to a comfortable sofa facing a TV. Natural light fills the room, highlighting the wooden flooring and exposed beams.

Cottage in High Wycombe

4.97 out of 5 average rating, 315 reviews

Chiltern Barn at Wheeler End, Buckinghamshire

Chiltern Barn is a 230 year old converted hay barn in Wheeler End in Buckinghamshire - half way between London and Oxford, close to Marlow and Henley-on-Thames with easy access to the M40. Wheeler End is a small village in The Chilterns built around a large common. There is a friendly local pub, The Chequers and Lane End, less than mile away has local amenities, including a well stocked Londis, a newsagents, excellent farm shop, gastro-pub, Indian and Chinese takeaways, hair dressers etc.

Top guest favorite

A narrow, gravel pathway runs between two brick structures, leading to visible buildings in the distance. Lush greenery bordered by wooden fencing is present on the right side, while the left features windows from the semi-detached cottage, allowing for natural light.

Cottage in Bray

5 out of 5 average rating, 111 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, recently completely refurbished. It provides a stylish place to stay for those wishing to enjoy the comforts of home whilst availing themselves of the local amenities. First night's stay includes a continental breakfast.

Guest favorite

A modern kitchen area features a white kettle and retro-style toaster with wooden accents. The counter is light-colored with a sink visible, while a warm glow from under-cabinet lighting complements the exposed brick backsplash.

Cottage in Surrey

4.81 out of 5 average rating, 108 reviews

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.

Top guest favorite

An entrance gate marked 'Dolphin House' stands surrounded by lush greenery. A gravel driveway leads into the property, framed by trees that create a natural canopy overhead. The brick pillars of the gate feature intricate detailing, enhancing the welcoming ambiance of the entrance.

Cottage in Englefield Green

5 out of 5 average rating, 347 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.

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Boats are lined along a concrete dock beside a serene river. Colorful rowboats occupy the water, while a gentle breeze ripples the surface. A pathway leads to a nearby building, framed by lush trees and vibrant clouds in the blue sky.

Cottage in Windsor

4.83 out of 5 average rating, 107 reviews

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!

Guest favorite

A serene riverside scene showcases the reflection of a historic church tower and charming buildings along the water's edge. A suspension bridge extends across the river, with boats resting quietly beneath the clear blue sky, while ducks and swans glide gracefully on the surface.

Cottage in GB

4.94 out of 5 average rating, 175 reviews

Luxurious Barn between Marlow & Henley

A luxurious 2 bedroom detached maisonette barn with garden, terrace and outstanding views over the Chiltern Hills.Situated in the picturesque village of Medemenham, 2 miles from Marlow and 5 miles from Henley-on-Thames. Located opposite Danesfield House Hotel and with stunning woodland walks accessible straight from the property and easy access to the River and Harleyford Golf Course . The property has 2 parking spaces, air conditioning ,wifi .