Family-friendly vacation rentals in Windsor

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Top-rated family-friendly rentals in Windsor

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

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Top guest favorite
Home in Berkshire
4.96 out of 5 average rating, 114 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 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, 179 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 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.

Top guest favorite
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 in Oakley Green
4.98 out of 5 average rating, 160 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.

Guest favorite
A serene bedroom features a spacious bed adorned with neutral linens and decorative pillows. Soft, warm lighting is provided by two hanging lamps, while artwork decorates the walls. Fresh towels are neatly arranged on a textured blanket at the foot of the bed, alongside a woven basket.
Condo in Windsor
4.92 out of 5 average rating, 142 reviews

Royal Windsor Castle 5 min lux 2 Bed 2bath+Garden

Welcome to Central Windsor. Only a 10 -15 min walk to Windsor Castle - The long walk / Great Park -Local shops -Restaurants Cafes -Pubs -Arts centre -Theatre •Good transport links to London - Heathrow 20 minutes by taxi -702/703 buses to bottom of Grove road . Super comfy king size bed with en-suite wet room plenty of wardrobe space Small double bedroom & second bathroom (extra nightly charge p) Kitchenette Microwave Washing machine . Private Patio No smoking/ Vaping please

Top guest favorite
A conservatory area is highlighted by a large Union Jack artwork on a vibrant yellow wall. A grey corner sofa is adorned with various colored cushions, creating a comfortable seating arrangement around a wooden table. Natural light enters through a window beside the sofa.
Cottage in Windsor
4.97 out of 5 average rating, 338 reviews

Saddlers Rest perfect for LaplandUK & Legoland

A cosy 1860s Victorian cottage located opposite Windsor Racecourse. Just under a 3-5 minute drive to Windsor Castle and 8-10 minutes to Legoland, with an easy train ride to London via the Elizabeth Line. Lapland UK is only 20 minutes away by car. Ideal for families visiting Legoland and Windsor Castle, couples looking for a getaway, or friends seeking a relaxing time. Perfect for race days or events at Windsor Racecourse, with Dorney Lake just 10-15 minutes 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, 320 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
An open plan kitchen and living area is illuminated by natural light from the windows. Features include modern cabinetry, a tiled backsplash, and a dining area with two stools. A comfortable sofa with patterned cushions adds to the inviting atmosphere.
Apartment in Windsor and Maidenhead
4.87 out of 5 average rating, 159 reviews

Stylish 2 bedroom flat; parking included

Modern flat a short 10-15 minute walk into Windsor centre. The long walk is round the corner with beautiful views of Windsor Castle. Modern open plan kitchen living area with all working facilities available for use during your stay - oven, induction hob, fridge/freezer, dishwasher and washing machine. Wifi is available throughout the flat. The bedrooms have double beds; all sheets and towels provided. One bathroom with shower facilities.

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 and Maidenhead
4.96 out of 5 average rating, 398 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.

Guest favorite
A modern bedroom features a spacious bed with soft linens and a decorative green pillow. Sunlight filters through the window, illuminating a minimalist design. A mirrored wardrobe reflects the light and space, while a small plant adds a touch of greenery beside a bedside table.
Condo in Berkshire
4.93 out of 5 average rating, 121 reviews

Modern Windsor home with free off-street parking

Welcome to our stylish, child-friendly 2-bed apartment in central Windsor! Ideal for families, couples, or a business stay. Just a short walk to Windsor Castle, shops and the train station. Legoland and Lapland UK are also closeby, plus there's easy access to London and Heathrow. Enjoy free parking, fast Wi-Fi, a fully equipped kitchen, and a spacious living area—perfect for relaxing after a day out.

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 Berkshire
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
4.9 out of 5 average rating, 103 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!

Popular amenities for Windsor family-friendly rentals

When is the best time to visit Windsor?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$34,230 GYDG$34,648 GYDG$35,691 GYDG$41,744 GYDG$43,623 GYDG$54,894 GYDG$54,268 GYDG$51,554 GYDG$47,171 GYDG$44,040 GYDG$42,162 GYDG$46,336 GYD
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Quick stats about vacation rentals that are family-friendly in Windsor

  • Total vacation rentals

    Explore 400 vacation rentals in Windsor

  • Nightly prices starting at

    Windsor vacation rentals start at G$10,436 GYD per night before taxes and fees

  • Verified guest reviews

    Over 13,020 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 80 rentals that welcome pets

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wi-Fi availability

    390 of Windsor vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windsor rentals

  • 4.8 Average rating

    Windsor stays are highly rated by guests—averaging 4.8 out of 5!

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