Holiday rentals in Old Windsor

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Top-rated holiday rentals in Old Windsor

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Guest favourite
The exterior view showcases a historic Mews property built of light-colored brick with a slate roof. Paved pathways lead through a well-maintained courtyard, bordered by greenery and mature trees. A secure, private entrance is visible, providing access to the residence.
Cottage
4.94 out of 5 average rating, 102 reviews

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.

Top guest favourite
A marching band of guards in red uniforms and tall black hats moves down a street lined with historic buildings. The scene captures the vibrant atmosphere of Windsor, as onlookers watch from above, framed by the charming architecture.
Apartment
4.99 out of 5 average rating, 134 reviews

Spacious & light 2bd, 2ba in the heart of Windsor

This beautiful 2bed, 2bath apartment, with parking, in the heart of Windsor, is an exceptional find. With Windsor Castle (watch the marching bands for the Changing of the Guard pass right outside your front door!), Windsor Great Park, The Guildhall, beautiful Eton and its own historic town centre with fabulous shops, restaurants, bars and clubs all only minutes away on foot, you couldn't be better placed for your stay. Windsor is also a very short drive from both Ascot Racecourse and Legoland.

Top guest favourite
Cabin
4.94 out of 5 average rating, 208 reviews

Gorgeous Self-Contained Wooden Cabin - Old Windsor

Beautiful and spacious self-contained log cabin comfortably sleeps 2-4. 1 king size bed, 1 small double sofa bed & 1 king size day bed (lounge). Shower/toilet, lounge and kitchenette. Close to Heathrow (7.4 miles / 15 mins) Great access to Windsor (2.4 miles). Close to a bus stop if needed. 2.5 miles to Runneymede where the Magna Carta was signed. Easy access to Ascot and Legoland The cabin is in the owner's garden. Friendly labrador included so please only book if comfortable around dogs!

Top guest favourite
The charming Victorian Lodge features a classic brick exterior with white trim, framed by lush greenery. Two inviting front windows and a central doorway are surrounded by decorative flower pots. A gravel pathway leads to the entrance, highlighted by an expansive tree nearby.
Cottage
4.99 out of 5 average rating, 102 reviews

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.

Guest favourite
A bright living area features two large sofas in green tones and a stylish glass coffee table. A dining table with four chairs is set for a meal, complemented by wall art and natural light from a window with curtains.
Flat
4.94 out of 5 average rating, 180 reviews

Apartment in Windsor

Newly refurbished apartment located 10 minutes walk from Windsor Castle and the town centre with all of its great shops, bars, restaurants and tourist attractions. Benefits from its own private entrance, double bedroom, wet room, kitchen and separate living room with 2 large sofas and dining area. Easy access to the M4 and only a 10 minute walk to the train station with direct links into London, it is ideally located for a business stay or as a base to explore Windsor and the surrounding area.

Guest favourite
The open-plan living area features a contemporary kitchen with sleek cabinetry and modern appliances. A glass coffee table sits atop a colorful area rug in front of a cozy sofa. Natural light fills the space through two windows, accented by a vase of fresh tulips.
Guest house
4.92 out of 5 average rating, 525 reviews

Luxury ♥️ 1 bed apartment Windsor Legoland Heathrow

Private self contained bungalow situated close to Windsor town centre. One-bedroom boutique style property plus a double pullout sofa bed, equipped with fully-fitted kitchen , lounge and bathroom with washing machine. Ideal for families visiting Legoland or historic Windsor, with excellent transport links, travel to central London takes just under an hour from Datchet station. Luxury features including a 'rain' shower, 400 thread count Egyptian cotton bedsheets Dolce gusto coffee machine

Top guest favourite
The cottage's serene garden is shown, featuring a stone patio with a wooden dining set surrounded by greenery. Sunny skies illuminate the exterior of the cottage, with trees and shrubs providing privacy and a peaceful atmosphere.
Cottage
5 out of 5 average rating, 151 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, 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.

Guest favourite
A cozy studio space is showcased, featuring a king-size bed with light bedding and decorative pillows. Natural light enters through large windows, illuminating the comfortable seating area with a patterned rug. A small bookshelf adorns the wall, adding a touch of warmth to the inviting atmosphere.
Flat
4.97 out of 5 average rating, 246 reviews

Stylish Studio-Walk to Windsor/Eton/Thames/Parking

Welcome to Crail Cottage in Datchet. Surrounded by beautiful greenery, there is plenty of wildlife and the River Thames is just behind the house. Take a walk to Windsor and Eton via the home park or the riverside. You can even walk to Eton through the school grounds from here. Our little studio is freshly decorated and welcomes you to stay. There is a new addition which is a King size bed with Hypnos mattress that will guarantee you a good night sleep. Perfect to relax after a busy day.

Top guest favourite
The yacht Oyster Fun'd is securely moored beside a tranquil river, showcasing its sleek exterior and spacious deck. Surrounding features include a paved pathway leading to the entrance, with views of other moored boats and natural scenery in the background.
Boat
4.97 out of 5 average rating, 377 reviews

Thames Relaxation 2 bedroom luxury Heated Yacht

Your EXCLUSIVE LUXURY EXPERIENCE on our spacious 42ft x15ft YACHT Oyster Fun’d Moored on the MainstreamThames on our PRIVATE Island *HEATING * 2 double bedrooms White cotton bedding WHITE COMPANY products 2 showers 2 electric toilets Galley fridge microwave induction hob 2 smart TVs Netflix Prime WIFI Seating area below and on deck far reaching views under the shadows of historical Runnymede Parking 1 for car. Designated smoking area . Cruises available during your stay .

Top guest favourite
A cozy living area features a comfortable white sofa adorned with striped cushions. Natural light filters through two windows with shades, highlighting a wooden coffee table and side table displaying a small vase of flowers. A mirror reflects the space, adding depth.
Cottage
5 out of 5 average rating, 374 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.

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
4.96 out of 5 average rating, 142 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
A cozy sitting room is featured, showcasing a comfortable armchair and a large coffee table adorned with various books and decorative items. A warm fire burns in the fireplace, and built-in shelving lines one wall, filled with a diverse selection of books.
Cottage
4.98 out of 5 average rating, 322 reviews

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 Ascot 9 mins to Legoland 11 mins to Ascot 16 mins to Windsor & Wentworth 30 mins to Henley-on-Thames Under 1 hour by train to London via nearby Bracknell station

Popular amenities for Old Windsor holiday rentals

When is the best time to visit Old Windsor?

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Avg. price£129£139£163£165£189£223£223£221£205£198£160£201
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Old Windsor?

    Old Windsor has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Old Windsor?

    Experience the best of Old Windsor with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Old Windsor?

    Four-legged friends are welcome in Old Windsor. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Old Windsor?

    Yes! Work meets play with ease at over 20 vacation rentals in Old Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Old Windsor have a kitchen?

    Absolutely! We offer over 30 house rentals with a kitchen in Old Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Old Windsor have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Old Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Old Windsor have free parking?

    Absolutely! We offer over 30 house rentals with free parking in Old Windsor. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Old Windsor?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with wifi, over 30 homes with a kitchen, over 30 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Old Windsor

  • Total holiday rentals

    Explore 60 holiday rentals in Old Windsor

  • Nightly prices starting at

    Old Windsor holiday rentals start at £30 per night before taxes and fees

  • Verified guest reviews

    Over 2,310 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 of Old Windsor holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Old Windsor rentals

  • 4.7 Average rating

    Old Windsor stays receive an average rating of 4.7 out of 5 from guests

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