
Cottage holiday rentals in Maidenhead
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Maidenhead holiday rentals start at $63 SGD per night before taxes and fees

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Guests love Kitchen, Wifi and Pool across Maidenhead rentals

4.9 Average rating
Maidenhead stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated cottage rentals in Maidenhead
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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.
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Gale Cottage
Gale Cottage combines classic country charm with modern styling. The Cottage looks out over a landscaped courtyard affording privacy and a stunning view including a medieval church and Grade 1 Listed surroundings. Part of the Dorney Court Estate, the Cottage is a stone's throw from Dorney Lake (2012 Olympic Venue) and a short walk to Dorney's wonderful Walled Garden Centre with its delightful cafe perfect for breakfast or lunch during your stay. Two village pubs are also conveniently close by.
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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
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Gorgeous CountryCottage overlooking Windsor Castle
The Victorian Lodge (1876) is a charming & quintessentially English country cottage on a private estate once owned by King Henry 8th. It sits right beside Windsor Great Park, at the entrance of a long driveway to Little Dower House, where the owners of the Lodge live. The private gardens and stunning view at the Victorian Lodge provide the perfect setting for a small intimate wedding. Whilst the romantic gardens within the Little Dower House estate provide an ideal venue for larger weddings.
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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. Air Con. Free EV charging point. Many public footpaths close by. Local shops are only a 10 minutes stroll. Gastro pubs, restaurants and independent shops within easy walking distance. A short drive from M25 (J11). Fast rail links to London from Woking. LGBTQ+ friendly. Friendly Spaniel and Siamese cat on site.
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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.
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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.
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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 9 mins to Legoland Walking distance to Lambrook School 10 mins to Swinley Forest, Go Ape, MTB bike park 11 mins to Ascot 16 mins to Windsor & Wentworth 30 mins to Henley 1 hour by train to London
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3 BR Victorian Cottage close to Windsor
The cottage offers generous living and bedroom space and a secluded garden. Ideal as a base from which to visit local sights such as Windsor, Legoland and Thorpe Park, and London is just over an hour journey to get into/from. Situated in the historic village of Colnbrook where there are good local amenities within a few minutes walk of the property; convenience store, The Ostrich Inn, take-aways and a children's playground. NB: Main Bathroom/WC are located on the ground floor.
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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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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 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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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 .
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Popular amenities for cottage rentals in Maidenhead
Cottage rentals with a hot tub

Luxury rural thatched cottage with cedar hot tub.
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Lavender Cottage
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5* Luxury Stylish House -LONG STAY discount
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6 Bed in Englefield Green (oc-e34166)
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Pond Cottage

Newly Refurbished Tidy Room in a Cosy Cottage
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Pet-friendly cottage rentals

Delightful, rural, modern cottage, large garden.
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Luxury Cottage near Oxford | Pub & Garden
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The Stables
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Self contained, rural cottage, 2 double bedrooms
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The Granary country cottage with private garden
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Very Pretty 2 BR Cottage On Edge of National Trust
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Delightful Period House with Sauna & Games Tables
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Walk to Windsor Castle-Grade II listed cottage
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Private cottage rentals

Family friendly - rural, detached, home from home
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Studio East & Petting Farm, Near Legoland-Lapland
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The Coach House
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Relaxing home near Legoland, Ascot, LaplandUK
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Beautiful Rose Cottage Barn on a farm in Surrey
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Period cottage, cosy sittingroom individual host
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Tawny's at Willow Barn
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Stunning Cottage, Perfect Location + Parking
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Destinations to explore
- Wembley Stadium
- Covent Garden
- Kings Cross
- Paddington
- Hampstead Heath
- St Pancras International
- London Bridge
- The O2
- ExCeL London
- Tower Bridge
- Silverstone Circuit
- Emirates Stadium
- Clapham Common
- Goodwood Motor Circuit
- Tottenham Hotspur Stadium
- Victoria Park
- University of Oxford
- Thorpe Park Resort
- The National Bowl
- Blenheim Palace
- Big Ben
- Buckingham Palace
- South Downs National Park
- Alexandra Palace





