
House vacation rentals in Maidenhead
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Quick stats about house rentals in Maidenhead

Total vacation rentals
Explore 160 vacation rentals in Maidenhead

Nightly prices starting at
Maidenhead vacation rentals start at $40 per night before taxes and fees

Verified guest reviews
Over 4,930 verified reviews to help you choose

Family-friendly vacation rentals
70 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
150 of Maidenhead vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Maidenhead rentals

4.8 Average rating
Maidenhead stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated house rentals in Maidenhead
Guests agree: these houses are highly rated for location, cleanliness, and more.

Magical Marlow town centre
Wing Cottage is a charming period terraced cottage with log burner in the heart of Marlow. It has been stylishly refurbished and has its own secluded courtyard garden. 5 minutes walk from High St shops with Everyman Cinema, Tom Kerridge’s Michelin* Hand &Flowers & The Coach, plus Marlow Ivy Garden, Côte Brasserie, Piccolino, The Compleat Angler and several historic pubs. The Park and Thames Path river walk are 10 minutes walk. Nearby bus stops serve neighbouring Henley-on-Thames (8 miles away).
ValueLocationHospitality

A Perfect Pad in Pangbourne!
The house was 'created' in 2020 having originally been part of the village pub - it’s now part of a redeveloped property which also includes the owners home and a fabulous cafe called Artichoke Cafe. The property is right in the heart of the picturesque riverside village of Pangbourne with its fabulous specialist shops, cafes, restaurants and pubs. Yet only ten minutes walk gets you to the countryside! The village also boasts a mainline station with direct trains to London Paddington.
ValueLocationGetting around

Luxury self-contained Annexe with balcony Jacuzzi
Luxury self-contained annexe on the edge of the Chilterns, situated in the peaceful countryside which can be enjoyed from the hot tub, yet only 5 mins to the M40, 15 mins to Oxford Park & Ride & 15 mins to the station with trains to London taking 45 mins. It is the perfect place to relax with cosy lounge, wood burning stove, bespoke kitchen & underfloor heating. Upstairs features a super-king sized bed, seating area, luxury wet-room with underfloor heating, balcony and Jacuzzi.
LocationValueWalkability

Fabulous Farm House in Skirmett
Valentine Farm House is newly refurbished to the highest standard and provides a wonderful base for a quick break or a longer stay, in the picturesque village of Skirmett, situated in the Hambleden Valley. Immerse yourself in country living in the Chilterns and enjoy the fantastic atmosphere of rural life. With horses to admire, right on your door step and unlimited walks, bike rides and local pubs to pop into, you're going to be falling in love with Valentine Farm.
FamilyLocationCleanliness

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.
LocationValueWalkability

Artists Victorian Semi
A charming Victorian semi on a quiet cul-de-sac with a beautifully landscaped garden where you’ll have two terraces, a comfy day bed, fire pit and gas BBQ to enjoy from May - September. Relax in the cosy living room with a working fire or in one of the two spacious double bedrooms. With Windsor, Marlow and Henley all only a 15 minute drive away or Maidenhead station a 25 minute walk with direct links to London, my home is situated in the perfect location.
ValueLocationSleep quality

18th century cottage
Self contained character annex in the beautiful Buckinghamshire countryside. Low ceilings and a narrow steep staircase with handrail and stairgates top and bottom. Parking spaces at the front and use of garden to the rear. Fantastic location on the edge of the Chilterns; good road and rail links to London, Oxford and Wembley. Close to the Thames, Windsor, Marlow, Cliveden, Hedsor House, Harry Potter Studios and Legoland. Plus there’s a pub next door!
ValueLocationAccess

Chiltern Retreat | Last-Minute Stays Welcome
Set in a peaceful rural location near Saunderton Station, this family-friendly home offers scenic countryside walks and nearby golf courses. Ideally placed for exploring Coombe Hill, Chequers, Waddesdon Manor, the Hellfire Caves and the Roald Dahl Museum, all just a short drive away. The house features a fully equipped kitchen, 65-inch TV, utility room and downstairs bathroom, providing comfort, space and everything needed for a relaxing stay.
ValueFamilyKitchen

Spacious, Family Home - With Parking & Garden
Welcome to Brook House – a spacious family home nestled on the banks of a beautiful brook in Maidenhead. Perfect for families or small groups of friends, this well designed four-bedroom property, combines comfort and practicality. Benefitting from a good sized garden, with outdoor seating and patio area, and terrace. The front drive allows for parking for multiple cars. There is also a room setup as a dedicated workspace.
LocationFamilyAccuracy

Racecourse Marina Lodge | Hot tub | Parking | EV
Live your high life on Windsor Racecourse Marina! Discover your dream get away with this beautifully designed luxury lodge located in a prestigious gated community. This property is perfect for a couple or a family looking to enjoy a relaxing luxurious lifestyle in tranquillity and peace. With amazing views over Windsor Racecourse and the boats moored on the marina, every moment here is a picture of calm elegance.
LocationFamilyAmenities

Private annexe in Old Windsor.
A private double bedroom annexe, with its own entrance, separated from main house. Private bathroom and full use of the gymnasium and lovely garden. (which includes a small wood area). The house is situated right on the doorstep of Windsor Great Park, in Old Windsor. Windsor town centre is 3 miles away and we are close to Heathrow and the M25 and M4.
FamilyLocationHospitality

Home in Marlow
If you’re looking for a quiet central location (with the luxury of parking), in a spacious and stylish modern newly renovated extension then this is the place for you! Whether you're looking to relax and unwind or enjoy the many bars, restaurants and shops that Marlow has to offer, this is a great place to stay.
FamilyLocationHospitality
Popular amenities for Maidenhead house rentals
House rentals with a pool

Surrey Cottage with indoor heated swimming pool
LocationFamilyAmenities

Wellness Escape by River: Sauna, Pool, Hot Tub
LocationValueAmenities

The Mill House
LocationFamilyCondition

Spacious Home Heated Pool(April-Sep) in Tilehurst
ValueLocationIndoor spaces

South Wing of Country House
ValueLocationWalkability

Stunning hideaway house
LocationFamilyGrill

Barn conversion, Henley-on-Thames
LocationValueCleanliness

The Pool House
ValueLocationSleep quality
Weekly house rentals

The Lookout - 2 beds, private garden & parking
LocationValueIndoor spaces

Family 6 Bed | Gated Parking, Sleeps 11, Bray
HospitalityCleanlinessAmenities

Quiet Retreat in Holyport
LocationValueQuiet

Stylish Townhouse with Parking & Modern Comfort
ValueFamilyKitchen

The Crafty Fox Beaconsfield
LocationFamilyWalkability

6-7 Bedroom, 260sqm, 4 x parking + street
ValueFamilyAccuracy

Bright & Spacious Home 10 min from Elizabeth line
ValueLocationOutdoor spaces

Cottage in Hurst
ValueFamilyLayout
Private house rentals

Spacious, level, luxury home with log burner
ValueLocationComfort

Olcote by Fullards
FamilyLocationCheck-in

Lux House, Jennett's Park
LocationFamilyIndoor spaces

Windsor Castle escape w/ private hot tub
LocationFamilyLayout

3BR Cottage • Lovely Garden & FREE Parking
LocationFamilyWalkability

Wild Acre Retreats Thatched Cottage on 2.5 Acres
LocationFamilyCleanliness

Countryside Escape
LocationFamilyWifi

Serene Home in Leafy Warfield with Private Garden
FamilyValueLaundry
When is the best time to visit Maidenhead?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $121 | $115 | $105 | $117 | $119 | $123 | $115 | $114 | $114 | $98 | $92 | $113 |
| Avg. temp | 42°F | 42°F | 46°F | 51°F | 57°F | 62°F | 66°F | 66°F | 61°F | 54°F | 47°F | 43°F |
Destinations to explore
- Wembley Stadium
- Covent Garden
- Kings Cross
- Paddington
- Hampstead Heath
- London Bridge
- St Pancras International
- ExCeL London
- The O2
- Tottenham Hotspur Stadium
- Silverstone Circuit
- Emirates Stadium
- Tower Bridge
- Goodwood Motor Circuit
- Clapham Common
- University of Oxford
- South Downs National Park
- Thorpe Park Resort
- Chessington World of Adventures Resort
- Victoria Park
- Blenheim Palace
- LEGOLAND® Windsor Resort
- Buckingham Palace
- Big Ben
- Family travel hub Tips and inspiration
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- Kid-friendly state parks Check out these family-friendly hikes





