
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.

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.

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 Cottage, dogs welcome, private garden .
A pretty cottage fully equipped for a comfortable holiday/ stay! Set back from the road, a peaceful haven. Private garden & parking. Easy walk to all local amenities & The River Thames. Great pubs &Michelin Star restaurants locally. The Chiltern Way offers a stunning path to all cyclists & walkers. Gorgeous old Towns of Windsor ( Legoland& Castle) Henley( Regatta & Festival)& Marlow (Tom Kerridge) , Cliveden, The Stanley Spencer Gallery,Train -London Paddington. M4 M40, Bicester Village .

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

Self-contained studio Wokingham
A self-contained newly build 20 m2 studio with separate entrance and parking. The studio is comprised of an en-suite bathroom, a super-king bed, a tall boy and a work desk. A kitchenette just next to the room with fridge freezer, microwave, kettle, toaster, coffee machine, washing machine and a tumble dryer. “The kitchenette doesn’t have a stove or an oven.” The studio is brand new and built to high standards. The studio is a 15 minutes walk to Wokingham train station and town centre.

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.

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

The Old School House, Ascot, Berkshire
Beautiful small self-contained character cottage set within private garden, one mile from Ascot. Open plan studio room with sitting area, kitchenette and bedroom area; en suite shower room/WC. Perfect for 1-2 adult guests looking for a comfortable and relaxing place to stay, whether for business or pleasure. It is ideal for visitors to Ascot Races, Windsor, close to Heathrow and a lovely rural retreat less than one hour from central London.
Popular amenities for Windsor and Maidenhead vacation rentals
Stay near Windsor and Maidenhead's top sights
Other great vacation rentals in Windsor and Maidenhead

Quiet Stay w/ King Bed & Parking near Station

Charming Garden Cabin Retreat

Epic Location, Views & Private Terrace

Wonderful 5 Bed Windsor | Free Parking, Own Garden

Self Contained - Spacious Studio Local to Windsor

Artists Victorian Semi

Design-Led-2xSuper-King Bed-2xEnsuites W Parking

Robin’s Rest @ Scotlands House
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 | R2,294 ZAR | R2,207 ZAR | R2,259 ZAR | R2,470 ZAR | R2,627 ZAR | R2,925 ZAR | R2,995 ZAR | R2,943 ZAR | R2,750 ZAR | R2,505 ZAR | R2,435 ZAR | R2,540 ZAR |
| 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 Windsor and Maidenhead?
Windsor and Maidenhead has more than 1,220 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in serviced apartment rentals in Windsor and Maidenhead?
Experience the best of Windsor and Maidenhead with our serviced apartment 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 Windsor and Maidenhead?
Four-legged friends are welcome in Windsor and Maidenhead. Choose from more than 530 vacation rentals for guests traveling with pets.
Do apartment rentals in Windsor and Maidenhead have air conditioning?
Absolutely! We offer over 30 apartment rentals with air conditioning in Windsor and Maidenhead. Enjoy a tailored experience with all the comforts you desire.
Do guesthouse rentals in Windsor and Maidenhead have a kitchen?
Absolutely! We offer over 50 guesthouse rentals with a kitchen in Windsor and Maidenhead. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Windsor and Maidenhead?
Yes! Work meets play with ease at over 1,000 vacation rentals in Windsor and Maidenhead featuring dedicated workspaces. Stay connected and productive in your home away from home.
Where should I stay in Windsor and Maidenhead?
Make yourself at home in Windsor and Maidenhead by choosing from our most frequently booked neighborhoods. We have over 150 vacation rentals in Touchen-End, over 1,060 vacation rentals in Eton Wick, and over 180 vacation rentals in Britwell.
Are there Windsor and Maidenhead vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 60 vacation homes with pools in Windsor and Maidenhead, available on Airbnb. Make a splash and soak up the sun in style!
Do bed and breakfast rentals in Windsor and Maidenhead have wifi?
Absolutely! We offer over 20 bed and breakfast rentals with wifi in Windsor and Maidenhead. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Condo Rentals in Windsor and Maidenhead?
Enhance your stay in our Condo Rentals with the most popular amenities: over 180 homes with wifi, over 180 homes with a kitchen, over 130 homes with free parking, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
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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- British Museum
- Covent Garden
- Buckingham Palace
- Big Ben
- Trafalgar Square
- Tower Bridge
- The O2
- London Bridge
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