
Holiday rentals in Maidenhead
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Top-rated holiday rentals in Maidenhead
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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.

The Studio in Maidenhead Riverside, Berkshire, UK.
LARGE STUDIO: (T0) A large self-contained quiet studio with UK size 2m double bed, en-suite bathroom and kitchenette with it's own private entrance. Attached to our house. There is off-street parking for 1 guest car. Convenient for the A4, M4, M40 M25 London is 25 miles. Heathrow Airport is 15 minutes away by car.. Direct trains into London. The Elizabeth Line train runs from Maidenhead station direct to London and the West End. Good for Windsor, Ascot, River Thames, Pinewood Studios etc.

Charming terrace in the heart of Bray village
Our lovely victorian terraced home is perfectly situated for all the fine dining that the charming village of Bray has to offer. The Michelin 3-starred Waterside Inn and Fat Duck are a few mins walk away as are the Crown Inn, Hinds Head and Caldesi. Stroll 15 mins more and you’ll find the recently renovated Monkey Island Estate. A short drive and you can be at either Ascot or Windsor Races, Cliveden House, Legoland, the village of Cookham or the beautiful river Thames towns of Marlow or Henley

A Hidden Gem
A character cottage, tucked away, in the heart of gastronomic Bray - renowned for its Michelin-starred restaurants: The Waterside, The Fat Duck, the Hind's Head and Caldesi, all within easy walking distance of the cottage. Lych Cottage is a two-bed semi-detached property, completed to a high standard. It provides a stylish place to stay for those wishing to enjoy the comforts of home whilst availing themselves of the local amenities. The first night's stay includes a continental breakfast.

Completely separate self-contained studio flat
Self-contained double room with en-suite shower room and kitchen area. Private access and parking. Completely private stand-alone studio but part of our home. Suitable for professional person/couple for short let periods. Ideal Monday-Friday but good for weekends to visit local area too. Free wi-fi, TV. A car is essential. Located in White Waltham village just outside Maidenhead. Easy access to Junction 8/9 of M4 and Maidenhead station. Also handy for Windsor, Henley, Ascot, Reading

Charming Garden Cabin Retreat
Charming cabin, clean, quiet & cosy. Newly built and furnished. Bedroom, bathroom, living room. Kitchen has microwave, oven, hob & fridge/freezer, larder. TV includes Netflix & Prime. High speed Broadband. Quiet & private garden area with fire pit. Close to M4/M40 & Heathrow. Near Windsor, Marlow, Cookham & Henley. Ten minutes walk from the River Thames/Boulters Lock/Thames Path. Cliveden House & Bray Michelin starred restaurants close. For 2 guests maximum. Not suitable for children.

Family & Contractor Friendly sleeps 8 Maidenhead
Our beautiful 3 Bed Townhouse that sleep 8 with 2.5 bathrooms. 6 minutes drive to Maidenhead Town Centre & train station (Elizabeth Line-24 min Paddington) 19 minutes drive to Windsor Castle 20 minutes drive to LegoLand Key Features: ? 3 bed townhouse ( Sleeps up to 8) ? Prime Location ? Free private parking for 2 cars ? Fast Wi-Fi & Smart TV ? Professionally cleaned with fresh linen provided ? Easy self-check-in & 24/7 guest support ? Fully equipped kitchen – cook meals at

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.

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 Ascot 9 mins to Legoland 11 mins to Ascot 16 mins to Windsor & Wentworth 30 mins to Henley-on-Thames Under 1 hour by train to London via nearby Bracknell station

Cheerful modern apt central Maidenhead, parking
Quiet location with free driveway parking, excellent road/rail links to London. On a tree lined street, 7 minutes walk from the Town Centre and Railway Station (London or Oxford 1hr max) The private space includes 2 double bedrooms, a large bathroom, en-suite shower room, a well equipped kitchenette and a relaxing lounge area Maidenhead Town Centre is being transformed with new restaurants, bars, coffee shops, and a new Leisure Centre 20 mins walk

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.

Beautiful self catering 2 bed Cottage
This beautifully restored Wheelwrights has been transformed into a contemporary 2 bedroom, (one kingsize bed. One twin beds) 2 bathroom cottage with all the luxuries of a modern home, and yet maintaining its original oak beams, vaulted ceilings and light gallery. This is a wonderful venue for couples, friends and families.
Popular amenities for Maidenhead holiday rentals
Other great holiday rentals in Maidenhead

Victorian Garden Central House by underground

Quiet 2BR King Bed + Parking + Close to Station

The Green Views Work Contractors, Family, Travels

Private Garden Annex with Own Entrance

Modern 2 Bedroom Victorian Gem in Henley-On-Thames

1 bed flat, Maidenhead town centre, with parking.

Sleeps 4 Maidenhead Windsor Ascot Legoland

Charming Annexe in Maidenhead
When is the best time to visit Maidenhead?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $145 SGD | $152 SGD | $143 SGD | $158 SGD | $149 SGD | $154 SGD | $172 SGD | $166 SGD | $152 SGD | $150 SGD | $141 SGD | $144 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 |
Frequently Asked Questions
Are there family-friendly vacation rentals in Maidenhead?
Maidenhead has more than 130 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in condo rentals in Maidenhead?
Experience the best of Maidenhead with our condo rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Maidenhead?
Four-legged friends are welcome in Maidenhead. Choose from more than 60 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Maidenhead?
Yes! Work meets play with ease at over 130 vacation rentals in Maidenhead featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Maidenhead vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Maidenhead, available on Airbnb. Make a splash and soak up the sun in style!
Where should I stay in Maidenhead?
Make yourself at home in Maidenhead by choosing from our most frequently booked neighborhoods. We have over 680 vacation rentals in Maidenhead, over 1,700 vacation rentals in Taplow, and over 140 vacation rentals in Bray.
Do house rentals in Maidenhead have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Maidenhead. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Maidenhead have a kitchen?
Absolutely! We offer over 70 apartment rentals with a kitchen in Maidenhead. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Maidenhead have wifi?
Absolutely! We offer over 60 apartment rentals with wifi in Maidenhead. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Maidenhead have free parking?
Absolutely! We offer over 130 house rentals with free parking in Maidenhead. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Maidenhead

Total holiday rentals
Explore 310 holiday rentals in Maidenhead

Nightly prices starting at
Maidenhead holiday rentals start at $25 SGD per night before taxes and fees

Verified guest reviews
Over 9,770 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 60 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
130 properties have a dedicated workspace

Wifi availability
300 of Maidenhead holiday rentals include wifi access

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

4.7 Average rating
Maidenhead stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Pet-friendly rentals Maidenhead
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- South Downs National Park
- Paddington
- British Museum
- Covent Garden
- St Pancras International
- Hampstead Heath
- London Bridge
- Buckingham Palace
- Wembley Stadium
- Kings Cross
- Big Ben
- The O2
- Tower Bridge
- Marble Arch
- Tottenham Court Road
- Natural History Museum
- Trafalgar Square
- Piccadilly Theatre
- ExCeL London
- Emirates Stadium
- Battersea Power Station (disused)
- Royal Albert Hall
- Russell Square
- Olympia Events




