
House holiday rentals in Maidenhead
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Top-rated house rentals in Maidenhead
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Five Star Boutique House 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, beautiful bathrooms, abundant art and character; the properties 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 all within 6 miles. Central London is 35 minutes by train. Heathrow is 6 miles away.

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.

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).

Secluded River Thames Lodge with Spectacular Views
Herons is totally unique, a beautiful detached lodge situated on the banks of the River Thames. Beautiful interiors and the views are simply wonderful from sunrise to sunset. Herons is the perfect place to unwind and relax, just sit and watch the wildlife and the boats milling along the river. Nearby are the Thames Market towns of Wallingford, Henley and Abingdon and the beautiful surrounding countryside.The historic city of Oxford is only 8 miles away and Bicester Village is a 30 minute drive.

Pool House at Mill Cottage
The Pool House at Mill Cottage offers a unique riverside escape with exclusive access to a private pool (Mar 1st - Oct 1st 2025 & Apr 1st - Oct 1st 2026). Nestled on the Thames, enjoy easy access to riverside cafes and restaurants by foot or boat. The charming one-bedroom retreat features blackout blinds for restful nights, plus a small sofa bed for extra guests. Just minutes from Goring on Thames village and the train station, it also boasts a BBQ and outdoor seating area for relaxing evenings.

Virginia Water Family Getaway
Lambly Hill House – Holiday Rental in Virginia Water, Surrey Welcome to Lambly Hill House, a stylish and spacious 4-bedroom holiday rental in Virginia Water, Surrey. Perfect for families, golf visitors and business travellers, this beautifully renovated home offers modern comfort, peaceful surroundings and a private garden in one of Surrey’s most desirable locations. Located just a short walk from Virginia Water train station, Lambly Hill House provides easy connections to central London.

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.

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, 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

Home from home - 4 Double Bed House with Parking
Newly renovated house with 4 double bedrooms, 2 bath/shower rooms, Free Wi-Fi & off street parking for 4+ cars & a well maintained garden to the rear. We have tried to create a home from home for families and Contractors alike. All 4 bedrooms can be set up as either 2 x single beds or one king bed in each room. Located just off Farnham Rd (SL1), Slough Industrial estate and a wide range of shops and amenities are a short walk away, Slough train station is also 1.7 miles away.

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.

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

Chiltern Retreat | Walks, Work & Free Parking
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.
Popular amenities for house rentals in Maidenhead
House rentals with a pool

The Mill House

Spacious Home Heated Pool(April-Sep) in Tilehurst

Wellness Escape by River: Sauna, Pool, Hot Tub

Barn conversion, Henley-on-Thames

Large Island Home with Pool on the River Thames

Stunning hideaway house

Old Wharf Cottage

Family Friendly Country House - Pool & tennis
Weekly house rentals

Modern 2 Bedroom Victorian Gem in Henley-On-Thames

Cozy annex

Inclusive, garden area, near pubs, golf, tennis

Peaceful 4bdtownhse. Free parkn. Windsor&Heathrow

Your home from home that's so conveniently placed

15th-Century Thatched Cottage on 2.5 Acres

Roseleigh Cottage in the Heart of Cookham.

The Crafty Fox Beaconsfield
Private house rentals

Beautiful 3 Bed Cottage • Garden • Free Parking

4 Bedroom Luxury Home Features HotTub & Pool Table

Luxury House, Jennett's Park

Central Windsor open plan house with parking!

Cosy Cookham Cottage

Hill Lands - 2 Bedroom Home in Wargrave, Berkshire

Exquisite 4/bed home w/hot tub & dog friendly

Stunning Cosy Cottage in Hampshire Oakley
When is the best time to visit Maidenhead?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $155 SGD | $147 SGD | $135 SGD | $142 SGD | $119 SGD | $114 SGD | $147 SGD | $146 SGD | $146 SGD | $126 SGD | $118 SGD | $145 SGD |
| Avg. temp | 6°C | 6°C | 8°C | 11°C | 14°C | 17°C | 19°C | 19°C | 16°C | 12°C | 8°C | 6°C |
Quick stats about house rentals in Maidenhead

Total holiday rentals
Explore 150 holiday rentals in Maidenhead

Nightly prices starting at
Maidenhead holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 4,750 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wifi availability
150 of Maidenhead holiday rentals include wifi 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!
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- South Downs National Park
- Paddington
- Covent Garden
- St Pancras International
- British Museum
- Hampstead Heath
- Kings Cross
- The O2
- Wembley Stadium
- Buckingham Palace
- Marble Arch
- Tottenham Court Road
- Tower Bridge
- London Bridge
- Big Ben
- Trafalgar Square
- Emirates Stadium
- ExCeL London
- Battersea Power Station (disused)
- Royal Albert Hall
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- Olympia Events
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- Clapham Common





