
Vacation rentals in Windsor and Maidenhead
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Top-rated vacation rentals in Windsor and Maidenhead
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Self-contained Annex Studio Flat
The accommodation consists of a double bedroom with French doors opening onto a nice big garden. There is a fully fitted kitchen and a small bathroom with walk-in shower. Broadband, TV, fridge, washing machine and drier are all included. It is about 50 yards from Egham station which has regular trains to London, the journey taking about 40 minutes. The train goes to Waterloo Station which is very close to the London Eye and Westminster, with Buckingham Palace, St James Park, Trafalgar Square a short walk away. Heathrow Airport is 5 or 6 miles away. Egham is a small town, but it has some historic interest in that the Magna Carta was signed at Runnymede down the road by the river in 1215. Not far away is Windsor castle and Eton (where princes William and Harry, and David Cameron went to school). There is also some lovely countryside around and lovely walks.

Riverside Log Cabin+Luxury Hot Tub Spa+Copper bath
Charming, riverside log cabin on the bank of the Kennett, overlooking a nature reserve. Privately located in my back garden there is a large open plan room with 2 double sofa beds, sleeping 4, a slate bed pool table & Hi Fi system. There's a luxury en suite bathroom with copper bathtub, shower, basin & WC. There are basic kitchen facilities with kettle, toaster, double hot plate, microwave & grill, sink & refrigerator/freezer. A veranda with 2 bbq's & seats plus lower deck overlook the river.

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

Beautiful oak barn in peaceful countryside setting
Delightful detached barn crafted from French oak in a peaceful private lane on a gated country estate. Luxuriously appointed with full facilities for a short break or longer stay. Air Con. Free EV charging point. Many public footpaths close by. Local shops are only a 10 minutes stroll. Gastro pubs, restaurants and independent shops within easy walking distance. A short drive from M25 (J11). Fast rail links to London from Woking. LGBTQ+ friendly. Friendly Spaniel and Siamese cat on site.

The Brickmaker’s Loft
A newly fitted one bedroom apartment, with living area, full kitchen, large bedroom with king size bed, a full size single bed in the eaves, and an extra single bed if needed. We’ve kitted the Brickmaker’s Loft out with everything you would need. The kitchen has an oven, fridge, dishwasher, kettle, toaster, microwave and all the normal cooking bits, crockery etc. The bathroom has a walk-in shower, loo, and sink, and a washing machine if you need it. The bedroom is a lovely relaxing space.

Apartment 24 GERRARDS CROSS
Delightful fully self-contained luxury one double bed apartment with own private entrance (your host is an interior designer). 10 minute level walk to Gerrards Cross village with a vast variety of restaurants, supermarkets and shops. Located 25 minutes from London Marylebone by use of Chiltern Railway Services at Gerrards Cross Station (10-15 minute walk from property) and no more than 40 minute drive from London Heathrow. This accommodation will provide a home away from home experience.

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

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.

Stylish Studio-Walk to Windsor/Eton/Thames/Parking
Welcome to Crail Cottage in Datchet. Surrounded by beautiful greenery, there is plenty of wildlife and the River Thames is just behind the house. Take a walk to Windsor and Eton via the home park or the riverside. You can even walk to Eton through the school grounds from here. Our little studio is freshly decorated and welcomes you to stay. There is a new addition which is a King size bed with Hypnos mattress that will guarantee you a good night sleep. Perfect to relax after a busy day.

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.

Luxury Penthouse with Huge Balcony
Take a break in our luxurious penthouse. The enormous south-west facing balcony offers panoramic views of the sunset each evening, making it the perfect spot to relax after a day. The interior is bright and modern, with floor-to-ceiling windows and sliding doors that fill the space with natural light. The fully-equipped kitchen has everything you need to prepare meals, and the living room is outfitted with premium audio (Sonos) and TV for your entertainment.
Popular amenities for Windsor and Maidenhead vacation rentals
Other great vacation rentals in Windsor and Maidenhead

Historic Luxury Townhouse in Marlow

Little studio in Maidenhead

Stunning spacious Riverside House in the Chilterns

The Old School House, Ascot, Berkshire

Self-contained studio Wokingham

Windsor -Castle 5 min walk lux 2 Bed 2bath+Garden

Cheerful modern apt central Maidenhead, parking

Luxury contemporary Apartment
When is the best time to visit Windsor and Maidenhead?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ481 | ﺩ.ﺇ463 | ﺩ.ﺇ474 | ﺩ.ﺇ518 | ﺩ.ﺇ551 | ﺩ.ﺇ613 | ﺩ.ﺇ628 | ﺩ.ﺇ617 | ﺩ.ﺇ577 | ﺩ.ﺇ525 | ﺩ.ﺇ510 | ﺩ.ﺇ533 |
| 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
What are the best places to stay in Windsor and Maidenhead?
Windsor and Maidenhead has inviting neighborhoods near the river and around the historic town center. Staying in areas such as Windsor’s central district or Maidenhead’s riverside neighborhoods gives you easy access to local shops, parks, and landmarks.
What are the best things to do in Windsor and Maidenhead with kids?
Families can explore Windsor Castle, visit LEGOLAND Windsor Resort, and walk along scenic riverside paths. The area has parklands and hands-on museums that make for interactive outings.
What are some of the best things to do in Windsor and Maidenhead?
Windsor and Maidenhead has historic sites like Windsor Castle, scenic strolls by the Thames, and vibrant local markets. Exploring Eton College or relaxing in Windsor Great Park are often recommended experiences.
How is the weather in Windsor and Maidenhead?
Windsor and Maidenhead has mild winters around 37–48°F (3–9°C) and warmer summer days near 58–75°F (14–24°C). Rain is spread across the year, so a light waterproof jacket is handy for exploring outdoor sites.
What are the best places to visit in Windsor and Maidenhead?
Explore Windsor Castle, stroll through Windsor Great Park, and visit the charming streets near Eton College. Maidenhead’s riverside and the town’s vibrant markets are also popular spots.
What are some hiking trails in Windsor and Maidenhead?
Windsor Great Park has footpaths winding by woodlands and gardens, while the Thames Path offers scenic riverside walks. These trails welcome both relaxed and energetic hikers throughout the seasons.
What are some family activities we can do in Windsor and Maidenhead?
Families often explore Windsor Castle, enjoy playtime at LEGOLAND Windsor Resort, and picnic along the Thames. Local parks and interactive museums make for engaging and relaxing days out.
What are some of the best day trip ideas from Windsor and Maidenhead?
You can explore the historic market town of Marlow, stroll through Kew Gardens for botanical treasures, or discover Oxford’s famous university area for culture and architecture. Each destination has unique attractions and local flavors to enjoy.
Are there any pet friendly accommodations available in Windsor and Maidenhead?
Windsor and Maidenhead has pet-friendly stays, especially in riverside neighborhoods and near public parks. Many hosts welcome pets, making it easy to explore local trails and green spaces with your companion.
What are some local tips for visiting Windsor and Maidenhead?
Consider joining a guided walk by the Thames for local insights, and explore markets for regional flavors and artisan goods. Public transport connects many popular sites around town, and comfortable shoes help with cobbled streets and trails.
What is Windsor and Maidenhead known for?
Windsor and Maidenhead is known for the iconic Windsor Castle, riverside views, and rich royal history. The area has vibrant markets, scenic parks, and cultural sites rooted in centuries of tradition.
What are the best hidden gems to explore in Windsor and Maidenhead?
Explore Dorney Court, a Tudor manor with local history, or stroll Bray village’s quiet lanes known for charming pubs and gardens. The Alexandra Gardens are a peaceful spot for picnics along the Thames.
What are the best foods to try in Windsor and Maidenhead?
Windsor and Maidenhead has classic British fare such as roasted meats, savory pies, and local cheeses. Neighborhood pubs and seasonal markets are frequently suggested for sampling regional cooking and fresh produce.
What should I bring for a trip to Windsor and Maidenhead?
Bring comfortable walking shoes for cobbled streets and river paths, a rain jacket for occasional showers, and layers that suit year-round mild temperatures. A small daypack is useful for market visits or castle tours.
What is the nightlife in Windsor and Maidenhead like?
Nightlife in Windsor and Maidenhead includes lively pubs, relaxed wine bars, and venues with live music and comedy. Riverside areas and Windsor’s historic streets host a mix of local favorites for evening hangouts.
What are the most popular events or festivals in Windsor and Maidenhead?
The Royal Windsor Horse Show is often highlighted in spring, while Windsor Fringe Festival brings arts and performances in early autumn. Street fairs and food festivals around the river are popular community traditions.
Are there family friendly vacation rentals in Windsor and Maidenhead?
Many vacation rentals in Windsor and Maidenhead welcome families, especially in central neighborhoods or near local parks. Look for properties with easy access to walking paths, playgrounds, and cultural sites for convenient outings.
When is the best time to visit Windsor and Maidenhead?
Late spring through early autumn is frequently suggested for enjoying Windsor and Maidenhead, with warmer temperatures and outdoor festivals. Many visitors appreciate the area’s gardens and walks when flowers are in bloom.
Quick stats about vacation rentals in Windsor and Maidenhead

Total vacation rentals
Explore 2,520 vacation rentals in Windsor and Maidenhead

Verified guest reviews
Over 78,250 verified reviews to help you choose

Family-friendly vacation rentals
1,220 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 530 rentals that welcome pets

Vacation rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
1,020 properties have a dedicated workspace

Wi-Fi availability
2,430 of Windsor and Maidenhead vacation rentals include wi-fi access

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

4.7 Average rating
Windsor and Maidenhead stays receive an average rating of 4.7 out of 5 from guests

Nearby attractions
Windsor and Maidenhead's top spots, include Ascot Racecourse, Virginia Water Lake, and Odeon Maidenhead
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