Family-friendly vacation rentals in Old Windsor

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Top-rated family-friendly rentals in Old Windsor

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
Cabin in Old Windsor
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!

Guest favorite
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.
Guesthouse in Datchet
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 favorite
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 in Wraysbury
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 .

Guest favorite
A modern living area features a vibrant blue sofa adorned with soft cushions in varying shades of turquoise and pink. The industrial-style exposed brick wall and art piece create visual interest. A dining area with sleek chairs is visible adjacent to a glass coffee table.
Home in Englefield Green
4.91 out of 5 average rating, 176 reviews

Charming Mews House near Windsor Castle, London and Ascot

This Grade 11 listed Mews property was built in 1872 and offers contemporary, luxurious living space. Luxurious beds, a beautiful bathroom, 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
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, 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.

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, 353 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.

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, 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 favorite
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 in Warfield
4.98 out of 5 average rating, 324 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

Top guest favorite
A self-contained studio features a spacious double bed dressed in neutral linens, accented by yellow pillows and a decorative cushion. The kitchenette with modern appliances is visible in the background, complemented by simple shelving and a well-placed pendant light.
Apartment in Windsor
4.96 out of 5 average rating, 402 reviews

Windsor Great * Snug * Private Annexe with Parking

*stylish private annexe with off street parking for one car. * self contained studio attached to our family home. * suitable for up to 2 people only. * ideal for both work travellers (key box ) and tourists. * approx 21 m2 *quiet, leafy "Boltons" area. * 15\20 mins stroll to town centre and Castle. * 10 mins stroll to Long Walk and Great Park. * 5 mins cycle to Windsor Great Park cycle path. * local shop and pub 5-10 mins walk.

Top guest favorite
The living area features a leather sofa adorned with orange cushions, complemented by a comfortable blue chair. A wooden coffee table is centered, with a television mounted on the wall. Light filters through a large window, enhancing the bright, inviting space.
Townhouse in Windsor
4.97 out of 5 average rating, 104 reviews

Charming cottage in the heart of Windsor

Rose Cottage is a cosy, terraced Victorian house sleeping up to 5 people in the centre of Windsor. It's on a quiet side street close to independent shops and restaurants and just a few minutes walk from the castle. There are two railway stations in Windsor, Central and Riverside, both within walking distance of the cottage. The cottage is an ideal base for visiting Windsor and its many attractions.

Guest favorite
A modern kitchen is shown, featuring sleek cabinetry and a marble counter. Cooking appliances include a microwave, stovetop, and oven. Light is softly reflected on the tiled backsplash, enhancing the contemporary design. Ample storage is provided within the cabinets below.
Guest suite in Berkshire
4.91 out of 5 average rating, 107 reviews

1-Bedroom Guest Suite: Close to Heathrow & Windsor

Enjoy easy access to local conveniences in Slough and neighbouring areas like Windsor, Iver, Heathrow and London with this clean, reasonably-priced and homely guest suite. Perfect for couples, those visiting their families / friends, or tourists wishing to visit Windsor, wider Berkshire / Buckinghamshire and London, with close links to Heathrow for onward travel!

Top guest favorite
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, 137 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 family-friendly rentals

When is the best time to visit Old Windsor?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$42,468 GYDG$42,468 GYDG$58,158 GYDG$86,610 GYDG$90,794 GYDG$107,739 GYDG$104,601 GYDG$95,187 GYDG$90,794 GYDG$79,079 GYDG$48,953 GYDG$68,618 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$29,288 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