Family-friendly vacation rentals in Maidenhead

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Top-rated family-friendly rentals in Maidenhead

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

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Guest favorite

Guest suite in Amersham

4.96 out of 5 average rating, 309 reviews

Peaceful, self-contained apartment on two levels

Overlooking private garden, situated in historic old town of Amersham, the apartment, once lived in by Roald Dahl, is close to restaurants, pubs, coffee shops plus fashion boutiques. Own entrance, fitted kitchen with electric hob, oven, microwave, fridge, washing machine. Also sitting room with sofa-bed, TV & DVD player, double bedroom with TV, bathroom with bath and separate shower unit. Full central heating, free Wi-Fi. Secluded outside seating area. Unlimited free parking in High Street.

Sep 7 – 14

G$23,632 GYD per night

Guest favorite

Barn in Warfield

4.91 out of 5 average rating, 732 reviews

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. A few miles from Ascot and Royal Windsor, Train stations to London and Reading.

Apr 29 – May 6

G$23,519 GYD per night

Superhost

Cottage in Windsor

4.79 out of 5 average rating, 281 reviews

Gale Cottage

Gale Cottage combines classic country charm with modern styling. The Cottage looks out over a landscaped courtyard affording privacy and a stunning view including a medieval church and Grade 1 Listed surroundings. Part of the Dorney Court Estate, the Cottage is a stone's throw from Dorney Lake (2012 Olympic Venue) and a short walk to Dorney's wonderful Walled Garden Centre with its delightful cafe perfect for breakfast or lunch during your stay. Two village pubs are also conveniently close by.

Oct 23 – 30

G$37,731 GYD per night

Guest favorite

Home in Buckinghamshire

4.92 out of 5 average rating, 143 reviews

The Stables, Little Marlow

A fabulous, converted barn, located in the very desirable village of Little Marlow, Bucks. The property is set within 3/4 acre for your private use and has it's own private driveway + parking. The interior has underfloor heating, a wood burning stove, panelled walls, en-suite bathroom and a family bathroom. Little Marlow has been in numerous Midsomer Murder TV series. The village has two pubs, a cricket ground and a church. The property is a 10 min walk to the river Thames. AONB & cons. area

Apr 18 – 25

G$108,315 GYD per night

Guest favorite

Guest suite in Nr Bracknell

4.96 out of 5 average rating, 116 reviews

4 people, beautiful views, near Legoland & Lapland

Lovely, 2-bed modern apartment, fantastic views over the gardens. Spacious apartment for 4 people in a quiet countryside setting, 1.5 miles to the Lexicon town centre & excellent shops, entertainment, eating, cinema. 5 miles to Legoland, 3 miles to Ascot (the races). 50 minutes into London Waterloo or Paddington from Maidenhead in 18 minutes. *NEW* Meta Quest 2 available to rent Great fun for all the family! £ 15 per stay 2 x 4k TV's, Disney, Netflix and SNES mini Bikes available to hire

Aug 13 – 20

G$39,396 GYD per night

Guest favorite

Guesthouse in Thatcham

5.0 out of 5 average rating, 256 reviews

Manstone Cottage, Yattendon

Situated just outside the picturesque village of Yattendon, Manstone Cottage is surrounded by beautiful views of rolling country side. Spacious and elegantly furnished, with private parking the cottage is the ideal get away for couples, families or small groups. Within walking distance of the village with it's fantastic pub, shop, cafe, brewery and beauty salon you won't have much need to go far but it's also well situated for access to Newbury, Hungerford, Goring, Pangbourne and Henley.

Jan 6 – 13

G$41,685 GYD per night

Guest favorite

Cottage in Englefield Green

5.0 out of 5 average rating, 277 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.

Nov 19 – 26

G$42,891 GYD per night

Guest favorite

Apartment in Cookham

4.94 out of 5 average rating, 516 reviews

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.

May 26 – Jun 2

G$34,795 GYD per night

Guest favorite

Guest suite in Datchet

4.96 out of 5 average rating, 206 reviews

Self Contained Annex, Datchet

The flat at Littlecroft is a comfortable self-contained 1 bedroom annex to the main house that can sleep 4 ( one king bed and one double sofa bed). It's within 10 - 15 mins walking distance of Datchet village/station with both Windsor and London connections and a short drive from Heathrow and the motorway network.

Sep 8 – 15

G$18,961 GYD per night

Guest favorite

Apartment in Oxford

4.93 out of 5 average rating, 134 reviews

Newly refurbished apartment in Summertown Oxford

A newly renovated basement apartment in the heart of Summertown, a vibrant neighbourhood packed with cafes and shops. Situated in a quiet street, within a minute's walk of cafes, food shops, and bus stops, the apartment is also close to the city centre, Oxford Parkway railway station and routes out of the city.

Jul 12 – 19

G$23,127 GYD per night

Guest favorite

Condo in Henley-on-Thames

4.98 out of 5 average rating, 206 reviews

Delightful Sparkling Clean Flat in Central Henley

Little Beeches is a ground floor fully self contained annex off the main house. Parking in the driveway. The large bedroom has kingsize and single bed (sleeps 2-3) Situated in a private leafy lane 5 minutes walk from Henley Town centre, close to the river and all amenities.

Jan 29 – Feb 5

G$31,428 GYD per night

Guest favorite

Guesthouse in The Ayots

4.93 out of 5 average rating, 483 reviews

White Cottage Annexe with riverside garden hot tub

Detached riverside retreat in self-contained garden room ideal for 'staycations' or longer term lets. Rural position nestling adjacent to a ford close to Brocket Hall, St Albans and nearby London, which is less than an hour away.

Sep 29 – Oct 6

G$26,922 GYD per night