Family-friendly holiday rentals in Windsor

4.99 out of 5 average rating, 133 reviews

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.

Condo in Berkshire

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.

Home in Windsor and Maidenhead

The exterior of the Coach House displays a combination of traditional brickwork and modern design. Black doors are framed by large windows, while a small stone table with chairs is positioned by the entrance. Decorative plants add a touch of greenery to the inviting facade.

4.95 out of 5 average rating, 265 reviews

Historic building in the centre of Windsor.

Beautifully renovated 1850's Coach House. This is part of a building that housed Queen Victoria's Equerries at Windsor Castle. Based in central Windsor with private parking, the property is an ideal place for a staycation. Mess about on the river (boating, paddle boarding, swimming) or visit the many beauty spots in the area. Legoland, Windsor Great Park, Windsor Castle and Swinley mountain bike trails are all within easy reach. A unique property that we hope that you will love as much as us.

4.95 out of 5 average rating, 155 reviews

An open-plan kitchen and living area features a wooden countertop with bar seating. The room is illuminated by natural light from the skylight, highlighting the contrasting blue and white walls. A cozy sofa and decorative artwork create a welcoming space.

Guesthouse in Berkshire

Windsor Home with Free Parking

Welcome to our 1-bedroom, skylit, guest house with off-road parking & private patio. Located in a quiet cul-de-sac close to Legoland, Windsor Racecourse, and Windsor Castle, our home is the perfect retreat after a long day of sightseeing. The bedroom can be set up with either a kingsize bed or 2 singles on request, while the sofa bed can comfortably fit 2 people. Our family run Airbnb is a great fit for families with kids, a couple or a small group of friends. Any questions, please just ask!

4.95 out of 5 average rating, 109 reviews

A spacious lounge area features a comfortable sofa draped with a green throw and adorned with colorful cushions. A sleek side table stands nearby. Light wood flooring extends to a dining area, which includes a table surrounded by green chairs. A spiral staircase leads to the upper level.

Home in Berkshire

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.

4.95 out of 5 average rating, 178 reviews

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

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 suite in White Waltham

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.

4.94 out of 5 average rating, 445 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

4.97 out of 5 average rating, 234 reviews

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

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.

4.92 out of 5 average rating, 117 reviews

The historic brick exterior of the building is adorned with gothic-style windows, framed by lush greenery. A pathway leads through the landscaped gardens, where trees and shrubs offer a serene atmosphere. The architecture reflects the character of a Grade II listed structure.

Home in Windsor

The Truly Incredible Windsor Home, Free Parking

Welcome to your stay at this incredible and unique Grade II listed building- a stunning 3 bedroom house. Absolutely NO Parties and NO Events. I live close by and guests will be asked to leave immediately. No loud sounds after 10pm. We have to be very respectful of our neighbours. Walk to town in around 20 minutes where you will be able to visit all of the shops and sights. Alternatively hop in the car and drive to Legoland in around 5 minutes or Ascot Racecourse in just over 10.

4.98 out of 5 average rating, 309 reviews

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

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

Apartment in Windsor and Maidenhead

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.

4.87 out of 5 average rating, 158 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.

Apartment in Windsor and Maidenhead

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.

4.96 out of 5 average rating, 394 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.

4.95 out of 5 average rating, 101 reviews

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

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.

Popular amenities for Windsor family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.56 out of 5 average rating, 9 reviews

The living area features oak flooring and a blend of modern and traditional furnishings. A comfortable sofa and armchair surround a coffee table. A dining table is set for four, and large windows provide ample natural light, creating an inviting atmosphere.

Apartment in Windsor

2-Bedroom Windsor Apartment with parking / 15CC

5 out of 5 average rating, 37 reviews

A modern lodge is surrounded by a glass balustrade, offering a clear view of the outdoor terrace furnished with a dining table and chairs. The well-maintained lawn provides a vibrant green space, and large windows reflect the bright sky with scattered clouds.

Home in Berkshire

Racecourse Marina Lodge | Hot tub | Parking | EV

Shepherd’s hut in Addlestone

A wooden hut is nestled among lush greenery, surrounded by trees and shrubs. Steps lead up to the entrance, which is framed by large glass doors. A small seating area is visible in the garden, providing a relaxing outdoor space.

4.96 out of 5 average rating, 136 reviews

Tinkerbell Retreat

Place to stay in Chorleywood

4.92 out of 5 average rating, 180 reviews

Hilly Hideaway, Hot Tub Countryside Retreat

4.98 out of 5 average rating, 427 reviews

A riverside log cabin is nestled among trees, featuring a spacious deck and seating area overlooking the water. Lush greenery surrounds the outdoor space, creating a natural setting that invites relaxation. The cabin’s wooden structure blends harmoniously with its peaceful environment.

Cabin in Reading

Riverside Log Cabin+Luxury Hot Tub Spa+Copper bath

Treehouse in Hertfordshire

A rustic treehouse is elevated among leafy trees, connected by a wooden staircase. Surrounding foliage creates a serene environment, while a shaded area beneath features a bench and a fire pit. The natural setting offers a sense of privacy and tranquility.

4.96 out of 5 average rating, 238 reviews

Tree House - Hot Tub on balcony

4.94 out of 5 average rating, 355 reviews

An aerial view showcases the unique geo dome structure surrounded by lush greenery. A wooden deck leads to an outdoor seating area, fire pit, and hot tub. The tranquil setting emphasizes a peaceful retreat in nature.

Dome in West Horsley

Private Unique Dome | Glamping | Hot Tub | Surrey

5 out of 5 average rating, 259 reviews

A serene scene showcases a cottage surrounded by lush greenery and a private lake. Two swans glide across the calm water, while the cottage, with its wooden facade and sloped roof, is nestled among the trees, offering a peaceful retreat in nature.

Cottage in Sarratt

Crestyl Cottage riverside barn for 2 with hot tub

Family- and pet-friendly home rentals

4.89 out of 5 average rating, 556 reviews

A bright studio space features a spacious bed with crisp white linen, set against a backdrop of exposed wooden beams. A comfortable sofa is nearby, and sliding glass doors offer views of the garden, enhancing the feeling of openness and light.

Guesthouse in Cookham

Riverside Boathouse

4.8 out of 5 average rating, 219 reviews

The exterior of a Georgian townhouse is depicted, featuring a mix of white and brown brick facades. Bright red doors enhance the building's character, while multiple square windows provide natural light. A low iron railing suggests a welcoming approach to the entrance.

Townhouse in Berkshire

Stunning 3-bedroom castle view Windsor townhouse

4.98 out of 5 average rating, 185 reviews

The exterior of the Brickmaker’s Loft displays a charming white facade with brown accents and multiple arched windows. A spiral staircase leads to the entrance, and a well-maintained garden is visible, featuring lush green grass and flower beds along the edge.

Guesthouse in Binfield

The Brickmaker’s Loft

Guesthouse in Cookham Dean

A charming cottage is framed by a well-tended garden featuring a thatched roof. Comfortable seating is arranged on a grassy area, accompanied by a small table. The entrance door is flanked by windows adorned with flower pots, creating a welcoming look.

4.85 out of 5 average rating, 110 reviews

Charming Cottage, dogs welcome, private garden .

4.91 out of 5 average rating, 159 reviews

A well-equipped kitchen features white cabinetry and a wooden countertop. Essential appliances, including a microwave and kettle, are neatly arranged. Natural light enters through the door, highlighting the clean design and wall-mounted dishware. A small table adds functional space.

Guest suite in Reading

Lovely annex, courtyard garden and private access

4.9 out of 5 average rating, 192 reviews

The cottage features a charming brick and flint exterior, adorned with climbing foliage and pink flowers. A vibrant blue front door adds a pop of color, while the well-maintained garden includes lush greenery. Windows are symmetrically placed, allowing for generous natural light.

Home in Wooburn Green

18th century cottage

4.93 out of 5 average rating, 212 reviews

A bright kitchen features a wooden dining table surrounded by chairs, with a vase of tulips as a centerpiece. Bifold doors open to a spacious garden, framed by wooden fencing and lush greenery. Modern appliances and cabinetry complete the open space.

Home in Bracknell Forest

2 bed house, close to Town Centre

4.94 out of 5 average rating, 656 reviews

A spacious living area is highlighted by exposed wooden beams and a large window allowing natural light. Two soft white sofas are arranged around a wooden coffee table, with a flat-screen TV positioned on a black stand. A charming brick fireplace adds character to the room.

Apartment in Cookham

Old Butchers Wine Cellar 15th Century Apartment

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 54 reviews

A charming Mill House, featuring a stone exterior and a spacious front entrance. Lush green grass and neatly trimmed hedges frame the property, while flowering lavender lines the pathway leading to the door. A second building is visible to the right, enhancing the picturesque setting.

Home in Stadhampton

The Mill House

4.88 out of 5 average rating, 100 reviews

An indoor pool features a striking wooden ceiling with exposed beams. The tiled area includes a hot tub and a spacious swimming pool, both surrounded by large windows that allow natural light to fill the space. Scenic wall murals enhance the relaxation atmosphere.

Condo in Buckinghamshire

Luxury retreat with extensive leisure facilities

4.95 out of 5 average rating, 39 reviews

A comfortable sitting area is presented, featuring a dark sectional sofa and a coffee table atop a patterned rug. A television is positioned on a stand, and two lamps provide soft lighting. Natural light flows in through the windows, adorned with light curtains.

Apartment in Maidenhead

Spacious Sunny Apartment

5 out of 5 average rating, 78 reviews

The floating home features a green rooftop adorned with lounge chairs and a patterned rug. A wooden deck extends towards the water, while a hot tub is visible on an adjacent patio. A small boat rests alongside the structure, surrounded by greenery.

Island in Hampton

Tulana Taggs - floating home on idyllic island

4.99 out of 5 average rating, 137 reviews

An outdoor seating area features a circular table surrounded by dark wooden chairs. A barbeque grill stands nearby, and the surrounding garden is lush with greenery. The unique architecture of the property includes charming brick walls and vibrant green doors, framed by foliage.

Cottage in Chobham

The Coach House

4.99 out of 5 average rating, 77 reviews

A charming log cabin is nestled among greenery, with a gravel pathway leading to its entrance. Flowering plants are positioned around the cabin, and a tree provides shade in the foreground. The structure features large windows that invite natural light.

Guesthouse in Surrey

4 bedroom Lodge/Hotub-Pool in Surrey UK

4.98 out of 5 average rating, 55 reviews

The exterior of a converted barn is visible, showcasing a rustic structure with a clock tower. Large windows framed in wood offer glimpses of the welcoming interior. Well-maintained greenery and flower beds surround a gravel courtyard, creating a tranquil outdoor space.

Barn in Henley-on-Thames

Two Bed Large Countryside Barn with Indoor Pool