House vacation rentals in Old Windsor

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Top-rated house rentals in Old Windsor

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Guest favourite
The exterior of the property is displayed, featuring a blend of traditional and modern architecture. A courtyard with landscaped greenery is visible at the center, surrounded by the building's stone facade. Tall trees and blue skies add a serene backdrop to the scene.
Home in Englefield Green
4.87 out of 5 average rating, 173 reviews

Charming 5* Hse 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, a beautiful bathroom, abundant art and character; the property looks 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 favourite
The exterior of the Coach House displays a combination of traditional brickwork and modern design. Black doors are framed by large windows, while a small stone table with chairs is positioned by the entrance. Decorative plants add a touch of greenery to the inviting facade.
Home in Windsor and Maidenhead
4.95 out of 5 average rating, 262 reviews

Historic building in the centre of Windsor.

Beautifully renovated 1850's Coach House. This is part of a building that housed Queen Victoria's Equerries at Windsor Castle. Based in central Windsor with private parking, the property is an ideal place for a staycation. Mess about on the river (boating, paddle boarding, swimming) or visit the many beauty spots in the area. Legoland, Windsor Great Park, Windsor Castle and Swinley mountain bike trails are all within easy reach. A unique property that we hope that you will love as much as us.

Guest favourite
A cozy sleeping area features a double bed with a soft green bedspread and an assortment of pillows in various colors. A light pink throw blanket is neatly arranged across the bed. A bedside table holds a notebook, and a wardrobe is visible in the background.
Home in Ascot
4.95 out of 5 average rating, 154 reviews

Cosy private detached from main house large room

Private entrance,dressing room, large corner shower , making the area totally self sufficient and private. The living room area is the same room as the sleeping area. With a Divan bed, 1 double Sofa bed. 1.7 miles to Ascot Racecourse, 2 miles to Ascot Station, 4.5 miles to Legoland, 7 miles to Windsor, 9 miles to Thorpe Park. A 5 Minute drive to Lapland UK. 3.2 miles to Bracknell. Wifi, Sky and Smart TV. Fridge, kettle and microwave. For a family visit please message me to discuss a discount.

Guest favourite
A spacious lounge area features a comfortable sofa draped with a green throw and adorned with colorful cushions. A sleek side table stands nearby. Light wood flooring extends to a dining area, which includes a table surrounded by green chairs. A spiral staircase leads to the upper level.
Home in Berkshire
4.95 out of 5 average rating, 100 reviews

Windsor Cottage: Traditional English Charm

Only 20 minutes from London Heathrow Airport and ideally located in one of the most central terraces in Windsor, our cosy cottage is full of character and charm, with all the modern conveniences you'd expect. Perfect for a romantic get-away or a family sight-seeing trip. Windsor Cottage is an 1890's two bedroom terrace house that comfortably sleeps a family or 4 (+ travel cot). A home away from home, you will find all of the luxury and convenience expected of a traditional English cottage.

Superhost
The living room features a combination of comfortable seating, including a plush gray sofa and a vibrant yellow armchair. A smart TV is placed on a modern media console, while a patterned area rug adds warmth to the space. Natural light enters through large windows, enhancing the inviting atmosphere.
Home in Colnbrook
4.84 out of 5 average rating, 104 reviews

Shal Inn @ Heathrow – pick & Drop + Parking

Book this family &bussiness friendly,well connected to London and only 10 mins away from Heathrow airport. You are welcome to bring your car as free parking available on premises. Pick and drop to airport is also available on request. Public transport is only couple of mins walk away. Elizabeth line to central London from Langley station, which is 2 miles away. 20 mins by bus to Langley station Attractions Windsor Castle Legoland Windsor resort Thorpe park Chessington world of adventure

Superhost
The historic brick exterior of the building is adorned with gothic-style windows, framed by lush greenery. A pathway leads through the landscaped gardens, where trees and shrubs offer a serene atmosphere. The architecture reflects the character of a Grade II listed structure.
Home in Windsor
4.92 out of 5 average rating, 112 reviews

The Truly Incredible Windsor Home, Free Parking

Welcome to your stay at this incredible and unique Grade II listed building- a stunning 3 bedroom house. Absolutely NO Parties and NO Events. I live close by and guests will be asked to leave immediately. No loud sounds after 10pm. We have to be very respectful of our neighbours. Walk to town in around 20 minutes where you will be able to visit all of the shops and sights. Alternatively hop in the car and drive to Legoland in around 5 minutes or Ascot Racecourse in just over 10.

Top guest favourite
The exterior of the annexe is framed by leafy greenery, showcasing a wooden door with large window panes. Gravel pathways lead to raised garden beds, which are positioned beside the entrance, contributing to a serene and natural ambiance.
Home in Hampshire
4.99 out of 5 average rating, 102 reviews

"Annexe" - Private Studio With Garden

Enjoy easy access to everything in Farnborough and surrounding areas from this perfectly located home base. Private parking, Farnborough North train station 6 mins walk and Farnborough Main train station < 20 mins walk (35 mins to London Waterloo). Wifi, Netflix, private outdoor space, own entrance. Well equipped kitchen with various appliances. Free parking on site. Washing machine and tumble dryer available by request. Ideal for contractor working close by.

Superhost
A spacious lounge area features leather sofas positioned around a central glass coffee table. Large windows allow natural light to fill the room, while light-colored walls create a bright atmosphere. A flat-screen television is mounted on the wall, providing entertainment options.
Home in Horton
4.87 out of 5 average rating, 350 reviews

Modern, spacious 2 bedroom and secure parking

Modern and spacious 2 double bedroom bungalow is located 5 mins from Heathrow. Bus service to and from Heathrow T5. Windsor, Legoland with close proximity car. Liquid Leisure is merely 2 minutes drive and British Rail Wraysbury train station is within 5mins car or 20mins walk from the property and it goes to Windsor and Waterloo London. Secure gated parking, close to local travel amenities. Comfortably fits 4 and being a bungalow it is suitable for the elderly too.

Top guest favourite
A spacious terrace is furnished with wicker seating and a wooden table, providing a comfortable area for relaxation. The serene view of the river Thames is framed by lush greenery and a bright blue sky, creating a peaceful outdoor setting.
Home in Wraysbury
4.97 out of 5 average rating, 135 reviews

River Thames near Windsor, Heathrow & London

Our home sits on the beautiful river Thames in Wraysbury near Windsor. The river runs past the end of the garden. There is a large west facing terrace, from the master bedroom. There is a large living room, kitchen and dinning room. 3 double bedrooms. There's parking for 2 cars in the garden. Windsor, Windsor castle and Lego land are about 20mins away my car. From Wraysbury station you can get into London Waterloo in 42mins. Heathrow is only 15mins drive away.

Top guest favourite
The cottage features a charming brick and flint exterior, adorned with climbing foliage and pink flowers. A vibrant blue front door adds a pop of color, while the well-maintained garden includes lush greenery. Windows are symmetrically placed, allowing for generous natural light.
Home in Wooburn Green
4.9 out of 5 average rating, 187 reviews

18th century cottage

Self contained character annex in the beautiful Buckinghamshire countryside. Low ceilings and a narrow steep staircase with handrail and stair gates top and bottom. Parking spaces at the front and use of the pretty garden to the rear. Fantastic location on the edge of the Chilterns; good road and rail links to London and Oxford, close to the Thames, Windsor, Marlow, Cliveden, Hedsor House, Harry Potter Studios and Legoland. Plus there’s a pub next door!

Guest favourite
A cozy bedroom is depicted with a spacious bed adorned with light linens and a patterned headboard. Bold teal walls create a vibrant backdrop, complemented by artwork featuring a tree. Soft lighting is provided by stylish wall-mounted fixtures.
Home in Windsor and Maidenhead
4.9 out of 5 average rating, 108 reviews

Modern with parking near Windsor Castle & Legoland

A stylish one bedroom private flat close to Windsor town centre, Windsor Castle, Legoland and all other historic and regional attractions. A short drive to Thorpe Park, Virginia Water, Ascot and London Heathrow. The cozy flat can accommodate up to 2 guests with a king size bed that is available in a private bedroom. High speed WiFi throughout, 4K TV with Netflix & YouTube, high quality cotton bedding, toiletries and fresh towels.

Top guest favourite
A red-brick exterior features two separate white doors, leading into the private annexe. Solar panels are installed on the roof, and the surrounding area includes a paved patio with a smooth stone surface, complemented by greenery in the background.
Home in Old Windsor
4.94 out of 5 average rating, 128 reviews

Private annexe in Old Windsor.

A private double bedroom annexe, with its own entrance, separated from main house. Private bathroom and full use of the gymnasium and lovely garden. (which includes a small wood area). The house is situated right on the doorstep of Windsor Great Park, in Old Windsor. Windsor town centre is 3 miles away and we are close to Heathrow and the M25 and M4.

Popular amenities for Old Windsor house rentals

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Avg. price$286 CAD$286 CAD$368 CAD$407 CAD$415 CAD$620 CAD$619 CAD$551 CAD$407 CAD$444 CAD$343 CAD$368 CAD
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Quick stats about house rentals in Old Windsor

  • Total vacation rentals

    Explore 40 vacation rentals in Old Windsor

  • Nightly prices starting at

    Old Windsor vacation rentals start at $56 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,450 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 of Old Windsor vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Old Windsor rentals

  • 4.6 Average rating

    Old Windsor stays receive an average rating of 4.6 out of 5 from guests

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