Family-friendly vacation rentals in Windsor and Maidenhead

4.86 out of 5 average rating, 445 reviews

Guesthouse

Cosy Cabin Virginia Water/Longcross

A separate, detached self contained cabin with private access, situated next to our home . Our cosy cabin has a cosy living area with sofa, a fully equipped kitchen area, separate bathroom with shower and a double bedroom with a 4ft double bed, wardrobe and drawers. Heating/air conditioning. Tea, coffee, sugar and milk provided. Driveway parking space available on request (driveway may not be suitable for large vehicles, however there is plenty of free on street parking) Not suitable for infants

4.91 out of 5 average rating, 820 reviews

Barn

Delightful small converted barn

Unique newly converted small barn, bright, light and self contained. Sleeps 3 adults or 2 adults and 2 children (or 2 small adults) due to restricted height space in loft. Large gravel drive behind big, wooden gates for safe and easy parking. An assortment of Teas, coffee & biscuits. Breakfast is not provided. Situated down a country lane, within the garden of the house, walking distance to pubs and restaurants. Near Lapland UK, Legoland, Ascot, Windsor, Train stations to London and Reading

4.96 out of 5 average rating, 275 reviews

Place to stay

Cottage/Annex. B&B available

One large bedroom cottage with bathroom. Part of a 19th Century farmhouse set in 1 1/2 acre gardens. Mainline station/tube 25 mins walk & 4mins drive. 25 mins to London. 10 min to Pinewood & 15 to Leavesden. Convenient for Heathrow/Luton. Perfect to explore the Chilterns/Grand Union canal/the Harry Potter Experience. Egyptian cotton sheets, fluffy gowns, SMART TV, tea/coffee making facilities. Fridge and microwave on request. Room for 2 Adults and 1 small child or baby. Breakfast on request.

4.9 out of 5 average rating, 121 reviews

1 bed apartment. Village location. Heathrow 25mins

This one bedroom apartment is annexed within our family home but benefits from its own entrance and facilities. Quiet village location but easy access to transport links (Heathrow is 20 mins drive, London 35 mins on the train). We are on the edge of the Chilterns, an UNESCO recognised Area of Outstanding Natural Beauty. We are taking bookings using the Covid19 guidelines and legislation set out on the UK government website. If the road map changes then availability may also need to change.

4.93 out of 5 average rating, 109 reviews

5* Boutique House Nr Windsor Castle, Ascot, London

This Grade 11 listed Mews property was built in 1872 and offers contemporary, five star living space. Luxurious king size beds, beautiful bathrooms, abundant art and character; the property 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 within 6 miles. Central London is 35 minutes by train. Heathrow is 6 miles away.

4.92 out of 5 average rating, 135 reviews

Condo

Windsor - Castle 5 min walk lux 2bed 2 bath+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

5 out of 5 average rating, 347 reviews

Cottage

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.

4.87 out of 5 average rating, 337 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.

4.97 out of 5 average rating, 120 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.

Superhost

Apartment

4.75 out of 5 average rating, 174 reviews

Central Windsor Apartment Facing The Castle

A delightful 2 bedroom apartment facing Windsor Castle in the heart of the town center. Ideally placed to take advantage of the excellent range of shops, bars and restaurants that Windsor has to offer. Two train stations provide links to London. Activities include horse racing at both Windsor and Ascot, polo and horse riding in Windsor Great Park, golf at Sunningdale and Wentworth and rowing/boating on the River Thames. Ten minutes from Legoland.

4.94 out of 5 average rating, 621 reviews

Apartment

Old Butchers Wine Cellar 15th Century Apartment

Our restored 15th century apartment is in a unique position on Cookham High Street, located within 500 meters to 7 different restaurants and pubs and four Michelin Star restaurants within 3 miles. Situated above our beautiful wine shop with a pop up wine bar on Thursday, Friday and Saturday nights. We have very comfortable beds, 100% cotton sheets and towels. The perfect choice for couples, business travellers and families.