Family-friendly vacation rentals in Old Windsor

Find and book unique family-friendly homes on Airbnb

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$37,631 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,020 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

  • 4.7 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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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

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.

FamilyIndoor spacesLocation

4.95 out of 5 average rating, 261 reviews
Guest favorite
Cabin in Old Windsor

Cosy Cabin Retreat, 1–5 guests, 5 mins to Windsor

The Cosy Cabin is a peaceful retreat, ideal for couples or families up to 5. With two double bedrooms, a modern shower room, and comfortable open-plan lounge/kitchen/diner. Enjoy WiFi, Sky and Netflix, or explore nearby: Windsor Castle (5 mins), Legoland (10 mins), Thorpe Park (15 mins), Heathrow (20 minutes) and London under an hour by train. Perfect for romantic getaways and family breaks. Please note the access is through our utility room from a separate entrance into the garden to the cabin.

Indoor spacesFamilyWalkability

4.92 out of 5 average rating, 118 reviews
Guest favorite
The exterior of the property is displayed, featuring a blend of traditional and modern architecture. A courtyard with landscaped greenery is visible at the center, surrounded by the building's stone facade. Tall trees and blue skies add a serene backdrop to the scene.
Home in Englefield Green

Charming 5* Hse 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, a beautiful bathroom, abundant art and character; the property looks 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.

Indoor spacesKitchenHospitality

4.88 out of 5 average rating, 186 reviews
Guest favorite
Cabin in Old Windsor

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!

FamilyKitchenLocation

4.93 out of 5 average rating, 255 reviews
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 Old Windsor

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.

FamilyKitchenBreakfast

4.99 out of 5 average rating, 110 reviews
Guest favorite
A cozy corner showcases a rattan chair with a soft pillow next to a potted plant. A table lamp illuminates a side table, while artwork is displayed on the walls. Natural light enters through the glass doors, enhancing the intimate atmosphere.
Chalet in Old Windsor

The Potting Shed

The Potting Shed, is a characterful & cosy self contained annex that can sleep 1-4 people. Benefiting from a private sheltered courtyard garden for dining or just a morning coffee. Ample off street parking on a gated drive. Overlooking horse fields, the property is close to Windsor Castle, Legoland, river walks, Windsor Great Park, Saville Gardens, Runnymede & easy access into London & Heathrow by train, bus or car. Within 40 mins to central London, Oxford or Warner Bros. Harry Potter world.

KitchenIndoor spacesCheck-in

4.94 out of 5 average rating, 108 reviews
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 Bracknell Forest

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 9 mins to Legoland Walking distance to Lambrook School 10 mins to Swinley Forest, Go Ape, MTB bike park 11 mins to Ascot 16 mins to Windsor & Wentworth 30 mins to Henley 1 hour by train to London

FamilyKitchenParks

4.97 out of 5 average rating, 370 reviews
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

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.

FamilyIndoor spacesLaundry

4.97 out of 5 average rating, 280 reviews
Guest favorite
Cabin in Chorleywood

Sleep in the Trees - Hot Tub and Slide

The Owls treehouse is a fun filled family unit with a fantastic slide including a hot tub. 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 Morning' Why not book out of the ordinary and stay with us, we look forward to your stay at North Hill Farm

FamilyIndoor spacesCheckout

4.94 out of 5 average rating, 114 reviews
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

Oyster Fun’d the Ultimate Relaxation on Thames

Your EXCLUSIVE LUXURY EXPERIENCE on our spacious 42ft x15ft YACHT Oyster Fun’d Moored on the MainstreamThames on our PRIVATE Island *HEATING * AIRCONDITIONING* 2 double bedrooms 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.

FamilyKitchenGetting around

4.97 out of 5 average rating, 419 reviews
Top guest favorite
A serene riverside view showcases the flowing River Thames lined with moored boats. The expansive green garden gently slopes towards the water, framed by trees and flowering plants, providing a peaceful setting for relaxation.
Home in Wraysbury

Sunnycove - Riverfront House near Windsor

Sunnycove is a peaceful riverside family home located in a gated community on a tranquil island. With many attractions nearby and quick links to London, Windsor and Heathrow Airport, Sunnycove is an ideal place for a family getaway, a business break, or just a tranquil place to unwind. Sunnycove is set in half an acre of garden with amazing views of the River Thames. It makes it ideal to sit back and relax watching the world go by as people sail down the river on their boats.

Indoor spacesKitchenLocation

4.98 out of 5 average rating, 105 reviews
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

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.

FamilyIndoor spacesAccuracy

5.0 out of 5 average rating, 395 reviews

Popular amenities for Old Windsor family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
The spacious living area features high wooden beams and large windows that allow ample natural light. A fireplace is centrally located, framed by a mix of comfortable seating and a glass coffee table. A staircase leads to the upper level, enhancing the open design.
Barn in Buckinghamshire

Dorney/Windsor Family Getaway with Hot Tub

FamilyKitchenHeating

4.92 out of 5 average rating, 117 reviews
Top guest favorite
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

KitchenFamilyGetting around

4.98 out of 5 average rating, 466 reviews
Guest favorite
A charming black-clad cottage is softly illuminated by string lights, set against a dusk sky. A picnic table with floral centerpieces occupies the outdoor space, surrounded by a wooden fence. Warm light glows from the cottage windows, creating an inviting atmosphere.
Place to stay in Chorleywood

Hilly Hideaway. Luxury Glamping Retreat + Hot Tub

FamilyIndoor spacesCheck-in

4.93 out of 5 average rating, 253 reviews
Top guest favorite
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.
Shepherd’s hut in Addlestone

Tinkerbell Retreat

Indoor spacesFamilyAmenities

4.96 out of 5 average rating, 169 reviews
Top guest favorite
A modern pool house features expansive glass walls surrounded by lush greenery. The indoor pool is visible, complemented by an outdoor lounging area with a sunbed and a vibrant garden showcasing various plants and flowers. A natural landscape of trees frames the property.
Place to stay in South Oxfordshire

Luxury Pool House set in an Oxfordshire forest

KitchenIndoor spacesValue

4.97 out of 5 average rating, 104 reviews
Superhost
The farmhouse is set against a backdrop of lush green hills and trees, showcasing a distinct red-brick exterior. Rolling fields are visible in the foreground, complemented by a clear blue sky and scattered clouds, creating a serene countryside scene.
Home in Beaconsfield

Hillmotts Farm with secluded Hot Tub

Indoor spacesKitchenHot tub

4.82 out of 5 average rating, 129 reviews
Top guest favorite
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

FamilyIndoor spacesOutdoor spaces

5.0 out of 5 average rating, 281 reviews
Guest favorite
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

Unique Dome | Glamping | Hot Tub | Surrey | Adults

FamilyKitchenAccuracy

4.94 out of 5 average rating, 415 reviews

Family-friendly home rentals with a pool

Top guest favorite
A cozy kitchen area features light green cabinetry and a wooden countertop. Appliances, including a kettle and washing machine, are visible. Shelving with dishware adds a rustic touch. A soft rug lies on the tiled floor, contributing to the warm ambiance of the space.
Cottage in Chobham

The Cottage

KitchenIndoor spacesShared spaces

4.99 out of 5 average rating, 127 reviews
Top guest favorite
The exterior of the cottage is highlighted by its charming brick facade and large windows, surrounded by a lush garden filled with various plants. A seating area is visible in the garden, creating a serene outdoor space, complemented by flowering shrubs and trees.
Cottage in Buckinghamshire

Family friendly - rural, detached, home from home

KitchenIndoor spacesQuiet

4.97 out of 5 average rating, 421 reviews
Top guest favorite
Farm stay in Guildford

The Luxury Cottage – Surrey Countryside Retreat

FamilyIndoor spacesCleanliness

4.96 out of 5 average rating, 182 reviews
Top guest favorite
Lavender plants in full bloom are featured prominently in the foreground, with deep purple flowers contrasting against lush green foliage. In the background, a round, clock-topped structure can be seen, set amid a beautifully landscaped garden area.
Home in Frimley Green

Surrey Cottage with indoor heated swimming pool

FamilyKitchenAccuracy

4.98 out of 5 average rating, 118 reviews
Guest favorite
An indoor swimming pool is highlighted with a clear blue surface, surrounded by warm wooden paneling. Skylights allow natural light to fill the space, while a hot tub sits to one side. Large windows offer views of the surrounding greenery.
Cottage in Surrey

Delightful Cottage 15 Acre Estate + Pool + Hottub

KitchenIndoor spacesCleanliness

4.92 out of 5 average rating, 171 reviews
Guest favorite
A warm dining area is presented with a wooden table set for a meal. Elegant glassware, a candle, and wine bottles complement a bouquet of roses. Exposed brick walls enhance the rustic charm, while shelves display a curated selection of decor items.
Condo in Wandsworth

Luxury Battersea studio w open fire, close to Park

Indoor spacesKitchenSolo travel

4.86 out of 5 average rating, 460 reviews
Top guest favorite
The spacious outdoor area features a serene swimming pool surrounded by artificial grass. A hot tub and loungers are visible beside the pool, with a patio table and chairs positioned nearby. The charming chalet stands in the background, showcasing large glass doors.
Farm stay in Chinnor

The Pool House with Private Pool & Hot Tub

FamilyIndoor spacesView

4.93 out of 5 average rating, 147 reviews
Top guest favorite
An indoor pool is surrounded by elegant columns and mirrors, reflecting the calming blue water. Natural light enters through windows, illuminating the space. Potted plants are placed strategically, adding a touch of greenery to the tranquil setting.
Home in Englefield Green

South Wing of Country House

Indoor spacesAmenitiesCleanliness

5.0 out of 5 average rating, 18 reviews

When is the best time to visit Old Windsor?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$46,620 GYDG$51,637 GYDG$60,209 GYDG$77,979 GYDG$77,561 GYDG$74,634 GYDG$104,529 GYDG$95,122 GYDG$90,731 GYDG$79,024 GYDG$48,920 GYDG$68,571 GYD
Avg. temp6°C6°C8°C11°C14°C17°C19°C19°C16°C12°C8°C6°C