Family-friendly vacation rentals in Old Windsor

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Top-rated family-friendly rentals in Old Windsor

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Top guest favorite
A cozy bedroom is depicted with a double bed featuring decorative pillows. The walls are adorned with various framed artworks and photographs, contributing to a personalized aesthetic. A small nightstand is visible beside the bed, and an open door leads to a well-lit hallway.
Guest suite in Egham
4.94 out of 5 average rating, 220 reviews

Self-contained Annex Studio Flat

The accommodation consists of a double bedroom with French doors opening onto a nice big garden. There is a fully fitted kitchen and a small bathroom with walk-in shower. Broadband, TV, fridge, washing machine and drier are all included. It is about 50 yards from Egham station which has regular trains to London, the journey taking about 40 minutes. The train goes to Waterloo Station which is very close to the London Eye and Westminster, with Buckingham Palace, St James Park, Trafalgar Square a short walk away. Heathrow Airport is 5 or 6 miles away. Egham is a small town, but it has some historic interest in that the Magna Carta was signed at Runnymede down the road by the river in 1215. Not far away is Windsor castle and Eton (where princes William and Harry, and David Cameron went to school). There is also some lovely countryside around and lovely walks.

Guest favorite
A modern living area is depicted with a stylish sofa and armchair arrangement. Natural light enters through large windows, highlighting the wooden flooring. A flat-screen TV is mounted on the wall, while potted plants and decorative vases add a touch of greenery to the space.
Cottage in Englefield Green
4.89 out of 5 average rating, 197 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.

Top guest favorite
Cabin in Old Windsor
4.94 out of 5 average rating, 206 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 favorite
A cozy living area features a plush blue sofa adorned with colorful patterned cushions and a wooden coffee table at its center. A modern entertainment unit stands against a textured stone wall, while large patio doors open to a shared garden, allowing natural light to fill the space.
Guest suite in Whitley
4.97 out of 5 average rating, 314 reviews

Peaceful stay in Frimley village

Welcome to our Annex. Located down a restricted road it is both very safe and quiet. You will find the accommodation tastefully decorated with a comfortable bed, modern shower room and general work/dining area. The living area opens out through patio doors onto our shared garden. Ideally located for all transport links i.e. M3, A3, Main line trains to London and close to Heathrow (25 mins) and Gatwick (45mins). There is a hourly direct bus service to Heathrow (730/731 ) with the stop 200m away.

Top guest favorite
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 in Windsor
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 favorite
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.
Apartment in Berkshire
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.

Top guest favorite
A cozy sleeping area features a spacious bed with neutral bedding against a softly colored wall. A small armchair and a light-colored rug complement the wooden flooring. Wall-mounted shelves display framed images, and a small closet provides additional storage.
Guest suite in White Waltham
4.94 out of 5 average rating, 455 reviews

Completely separate self-contained studio flat

Self-contained double room with en-suite shower room and kitchen area. Private access and parking. Completely private stand-alone studio but part of our home. Suitable for professional person/couple for short let periods. Ideal Monday-Friday but good for weekends to visit local area too. Free wi-fi, TV. A car is essential. Located in White Waltham village just outside Maidenhead. Easy access to Junction 8/9 of M4 and Maidenhead station. Also handy for Windsor, Henley, Ascot, Reading

Guest favorite
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.
Apartment in Datchet
4.97 out of 5 average rating, 244 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.

Guest favorite
A cozy studio interior is shown, featuring a king-size bed against the wall with a light blue duvet and decorative pillows. A sofa bed in pastel tones is positioned nearby. Shelving contains framed photographs and decor items. A small desk and chair, along with a lamp, complete the space.
Condo in Surrey
4.91 out of 5 average rating, 132 reviews

Guest House in Wentworth, Virginia Water

Welcome to our cozy studio flat in the annex at our home! The space features a king-size bed, a sofa bed for 2 kids or 1 adult, a private bathroom, kitchenette, desk & Freeview TV. Perfectly located: - 5 min walk to Wentworth Golf Club - 5 min drive to Longcross Studios and Windsor Great Park - 15 min drive to Ascot Racecourse, Lapland LEGOLAND, Thorpe Park, Windsor Castle, Heathrow Pls confirm if you require both the King Size bed & Sofa Bed - £25 surcharge for 2 person bookings

Top guest favorite
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 in Englefield Green
5 out of 5 average rating, 373 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 favorite
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
4.96 out of 5 average rating, 141 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 favorite
A charming self-contained cottage is set within a lush private garden, characterized by brick exterior and a slate roof. A welcoming door leads to the entrance, framed by greenery and flowering plants, with a spacious lawn surrounding the building.
Cottage in Windsor and Maidenhead
4.96 out of 5 average rating, 833 reviews

The Old School House, Ascot, Berkshire

Beautiful small self-contained character cottage set within private garden, one mile from Ascot. Open plan studio room with sitting area, kitchenette and bedroom area; en suite shower room/WC. Perfect for 1-2 adult guests looking for a comfortable and relaxing place to stay, whether for business or pleasure. It is ideal for visitors to Ascot Races, Windsor, close to Heathrow and a lovely rural retreat less than one hour from central London.

Popular amenities for Old Windsor family-friendly rentals

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MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$42,472 GYDG$42,472 GYDG$58,164 GYDG$86,618 GYDG$90,802 GYDG$107,749 GYDG$104,611 GYDG$95,196 GYDG$90,802 GYDG$79,086 GYDG$48,958 GYDG$68,625 GYD
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Quick stats about vacation rentals that are family-friendly in Old Windsor

  • Total vacation rentals

    Explore 30 vacation rentals in Old Windsor

  • Nightly prices starting at

    Old Windsor vacation rentals start at G$29,291 GYD per night before taxes and fees

  • Verified guest reviews

    Over 940 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Old Windsor vacation rentals include wi-fi 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