Family-friendly holiday rentals in Old Windsor

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Old Windsor

  • Total holiday rentals

    Explore 30 holiday rentals in Old Windsor

  • Nightly prices starting at

    Old Windsor holiday rentals start at £136 per night before taxes and fees

  • Verified guest reviews

    Over 980 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 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

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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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, 103 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
Cabin
4.94 out of 5 average rating, 245 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 favourite
Cabin
4.94 out of 5 average rating, 104 reviews

Sleep in the Trees - Hot Tub, Sauna and Slide

The Owls treehouse is a fun filled family unit with a fantastic slide including a hot tub and sauna. With unusual tunnel shaped rooms looking out to beautiful woodland country side, this unique getaway is exciting to share with loved ones. Attractions include Harry Potter studios, 35min Trains to London, Legoland Windsor to name a few. Also Featured on 'Amazing small spaces' and 'This Moring' Why not book out of the ordinary and stay with us, we look forward to your stay at North Hill Farm

Top guest favourite
An outdoor roof terrace features a seating arrangement with a grey cushioned sofa and two armchairs facing a square coffee table. Lush greenery is affixed to the wall, providing a natural backdrop against the wooden decking.
Home
4.96 out of 5 average rating, 138 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.

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
4.95 out of 5 average rating, 185 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 exterior of a charming stone barn is illuminated at night, highlighting its rustic architecture. Soft lighting from below enhances the textures of the stone walls and draws attention to the barn doors. A sculptural feature is visible in the foreground, adding interest to the serene landscape.
Barn
4.95 out of 5 average rating, 235 reviews

17th Century Barn in quiet country village

A 17th Century Hay Barn 7 miles from Oxford and in the same village as ‘Le Manoir aux Quat’ Saisons’. Enjoy a glass of bubbles on your own private terrace before strolling to dinner at this famous Cotswold stone Manor. Fully wheelchair accessible & with private parking this unique property is the perfect place for a few days away walking in the nearby Chilterns, exploring Oxford’s Colleges & Cafes, visiting Art & Literary Fairs or attending appointments at Oxford’s many leading hospitals.

Top 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, 266 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
A modern sleeping area is featured, showcasing a unique bunk bed design with rounded windows. Soft lighting highlights the cozy bedding. A child is playfully seated in the upper space, emphasizing the fun and creative layout of the room.
Cottage
4.98 out of 5 average rating, 183 reviews

Studio West & Petting Farm-Near Legoland- Lapland

STUDIO WEST is located at Willow Court Farm in Oakley Green and only 5-10 minutes drive away from LEGOLAND, Lapland UK and Windsor town centre so is perfectly located for a great stay. We have private award winning detached open plan modern holiday studios providing unique accommodation with easy access to the all the fantastic places to visit in the surrounding area. Guests can feed the various animals on the farm including the 6 pigs, 9 pygmy goats, 6 sheep, turkey ducks and chicken.

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, 403 reviews

Thames Relaxation Luxury 2 bedroom 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 of the Thames near 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, 385 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
4.97 out of 5 average rating, 150 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.

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
4.97 out of 5 average rating, 347 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 family-friendly rentals

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