
Cottage holiday rentals in Windsor
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Top-rated cottage rentals in Windsor
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5* Boutique Hse Nr 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.

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.

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.

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. 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.

Upscale Bright Boutique Cottage Central St Albans
Our Cottage has been renovated from ground up and we are thrilled to present our "good life home". An experience of upscale casual elegance. Opting for a clean and uncluttered energy you will find our home equipped for the most discerning guests. A fully stocked gourmet kitchen with a Nespresso Citiz & Milk, a gas range cooking, Wall-to-wall window for natural light and a cosy outdoor lounge. The Living space displays contemporary décor, colours are serene and neutral and comfort is standard.

Studio East & Petting Farm, Near Legoland-Lapland
Studio East is a very cool, self contained, detached, self catering, open plan studio with private secure parking, large private fenced garden, free superfast WIFI with a 50 inch cable TV. There is also a small on site petting farm! Studio East has a king size bed along with bespoke bunk beds that the kids will just love and has a maximum occupancy of 2 adults and 2 children. Located in Oakley Green on the edge of Windsor and only 10 minutes from Windsor town centre, Lapland Uk and Legoland.

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.

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 Charming Windsor Cottage
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!
Popular amenities for Windsor cottage rentals
Cottage rentals with a hot tub

Newly Refurbished Tidy Room in a Cosy Cottage

Pond Cottage

5* Luxury Stylish House -LONG STAY discount

Lavender Cottage

Luxury rural thatched cottage with cedar hot tub.

3 Bed in Aylesbury (oc-88963)

2 Bed in Thame (oc-cc068)

Delightful Cottage 15 Acre Estate + Pool + Hottub
Pet-friendly cottage rentals

Gardeners’ Cottage (Georgian stable conversion)

Stylish Cottage near Oxford | Dogs | Village Pub

Wimbledon Village Sleeps 3 Cute Cottage

Delightful, rural, modern cottage, large garden.

Self contained, rural cottage, 2 double bedrooms

Stylish-Stays: Fleet, Patio, Pets, EV, Parking

The Stables

Modern Countryside Retreat with Stunning Views
Private cottage rentals

Charming Stylish Cottage at Windsor Great Park

Beautiful Two Bedroom Cottage

Victorian Cottage, Great Bookham near Leatherhead

Luxury Gatehouse in Rural Location

Walk to Windsor Castle-Grade II listed cottage

Flintstone Cottage in Boxmoor, Hemel Hempstead, UK

The Bakehouse, detached cottage

Stunning Design-led 2-bed 2- bath with parking
Quick stats about cottage rentals in Windsor

Total holiday rentals
Explore 10 holiday rentals in Windsor

Nightly prices starting at
Windsor holiday rentals start at $119 NZD per night before taxes and fees

Verified guest reviews
Over 1,240 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Wi-Fi availability
10 of Windsor holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Windsor rentals

4.8 Average rating
Windsor stays are highly rated by guests—averaging 4.8 out of 5!
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- South Downs National Park
- Paddington
- British Museum
- Covent Garden
- St Pancras International
- Hampstead Heath
- Kings Cross
- Wembley Stadium
- Buckingham Palace
- The O2
- London Bridge
- Tottenham Court Road
- Tower Bridge
- Marble Arch
- Big Ben
- Natural History Museum
- Piccadilly Theatre
- Trafalgar Square
- ExCeL London
- Emirates Stadium
- Battersea Power Station (disused)
- Royal Albert Hall
- Russell Square
- Olympia Events




