Best Vacation Homes in Windlesham
538 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
ZA R2,453/Night
For 7 Nights ZA R17,173
796.53 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- View
- Parking
ZA R4,441/Night
For 7 Nights ZA R31,079
Unlock the Best Price
5 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
ZA R5,789/Night
For 7 Nights ZA R40,520
430.56 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Balcony/Terrace
- View
- Parking
ZA R2,091/Night
For 7 Nights ZA R14,645
5 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
ZA R5,364/Night
For 7 Nights ZA R37,548
6 Guests
1 Bedroom
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
ZA R11,208/Night
For 7 Nights ZA R78,462
9 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
ZA R7,359/Night
For 7 Nights ZA R51,520
Windlesham Luxury Rentals
ZA R61,092/Night
For 7 Nights ZA R427,642
12 Guests
5 Bedrooms
7 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
ZA R53,413/Night
For 7 Nights ZA R373,889
2045 ft²
14 Guests
7 Bedrooms
4 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Pool
- Balcony/Terrace
ZA R53,354/Night
For 7 Nights ZA R373,479
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
ZA R48,962/Night
For 7 Nights ZA R342,728
12 Guests
6 Bedrooms
5 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
ZA R45,422/Night
For 7 Nights ZA R317,953
6372.23 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
ZA R23,365/Night
For 7 Nights ZA R163,557
17222.26 ft²
5 Guests
3 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- Breakfast
- Pet Friendly
ZA R17,658/Night
For 7 Nights ZA R123,595
6 Guests
3 Bedrooms
3 Bathrooms
Free Cancellation
House
- Parking
- Internet
- Child Friendly
ZA R15,129/Night
For 7 Nights ZA R105,897
Windlesham Pet Friendly Vacation Rentals
988 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
ZA R6,460/Night
For 7 Nights ZA R45,215
990.28 ft²
6 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- View
- Pet Friendly
ZA R6,524/Night
For 7 Nights ZA R45,675
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
ZA R5,960/Night
For 7 Nights ZA R41,718
129.17 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Villa
- View
- Pet Friendly
- Parking
ZA R5,940/Night
For 7 Nights ZA R41,587
8 Guests
3 Bedrooms
1 Bathroom
Pet Friendly
Cottage
- Fireplace/Heating
- Pet Friendly
- Internet
ZA R10,334/Night
For 7 Nights ZA R72,338
5 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
ZA R6,860/Night
For 7 Nights ZA R48,023
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
ZA R6,657/Night
For 7 Nights ZA R46,595
1615 ft²
7 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Ski Chalet
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
ZA R5,970/Night
For 7 Nights ZA R41,784
Windlesham Large Vacation Homes
5500 ft²
16 Guests
7 Bedrooms
6 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
ZA R38,664/Night
For 7 Nights ZA R270,652
9 Guests
5 Bedrooms
2 Bathrooms
Free Cancellation
House
- View
- Parking
- Internet
ZA R8,134/Night
For 7 Nights ZA R56,938
1292 ft²
14 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Kitchen
- Internet
- Child Friendly
ZA R5,996/Night
For 7 Nights ZA R41,981
10 Guests
3 Bedrooms
5 Bathrooms
Family Friendly
House
- Fireplace/Heating
- View
- Pet Friendly
ZA R4,227/Night
For 7 Nights ZA R29,585
1076 ft²
14 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
ZA R6,637/Night
For 7 Nights ZA R46,463
16 Guests
10 Bedrooms
10 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Kitchen
ZA R49,021/Night
For 7 Nights ZA R343,155
16 Guests
7 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Kitchen
ZA R41,913/Night
For 7 Nights ZA R293,391
14 Guests
8 Bedrooms
6 Bathrooms
Family Friendly
Villa
- Child Friendly
ZA R35,169/Night
For 7 Nights ZA R246,189
Why Choose Rent By Owner for your Windlesham Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Windlesham
When should you plan your Vacation Rentals stay?
Choosing the right time to vacation here can enhance your experience, as the region offers distinct charms throughout the year, making it essential to plan according to seasonal weather patterns and local events for an enjoyable stay in this destination.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warm weather that enhances your experience here, especially if you plan outdoor activities or relaxation by scenic views.
Average Temperature Daytime: around 21°C to 25°C - Nighttime: 13°C to 15°C
Late Spring (May)
This period marks the start of the peak season when the region’s natural beauty is in full bloom, making it ideal for exploring and outdoor pursuits.
Average Temperature Daytime: about 16°C to 20°C - Nighttime: 8°C to 11°C
Off-Season Highlights
Autumn (September to October)
As the foliage colors change, you’ll find fewer crowds, which provides a peaceful setting to enjoy the region's tranquil charm.
Average Temperature Daytime: around 14°C to 18°C - Nighttime: 7°C to 10°C
Winter (December to February)
During winter, the area becomes quieter, offering a cozy atmosphere perfect for those seeking solitude or a relaxing retreat away from the busier months.
Average Temperature Daytime: 4°C to 8°C - Nighttime: 1°C to 3°C
Weekly Weather Forecast for Windlesham
How to Book Your Windlesham Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Windlesham
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining spaces perfect for relaxing meals in the fresh air.
- Take advantage of private gardens or landscaped yards for outdoor leisure.
- Make use of patios or terraces for enjoying scenic views during your stay.
- Benefit from access to well-maintained lawns suitable for outdoor activities.
- Utilize outdoor lounging areas to unwind after exploring the region.
- Find properties with dedicated barbecue or grilling stations for outdoor cooking.
- Explore nearby walking trails or nature spots accessible directly from your rental.
Top Attractions Around Windlesham
What attractions are nearby?
In this charming area, you can enjoy a variety of outdoor activities and explore scenic countryside trails, all within easy reach of your vacation rental in Windlesham, England.
Family Activities
- Windlesham Golf Club: Enjoy a family-friendly day on the greens at this well-maintained golf course nestled in the region, offering activities suitable for all skill levels.
- The Look Out Discovery Centre: Engage with interactive exhibits and outdoor adventures that make learning about nature fun and accessible for children of all ages.
- Swinley Forest: Explore miles of scenic walking and cycling trails in this lush forest, perfect for a family picnic or outdoor exploration in the area.
- Wildlife Watching in Windsor Great Park: Discover local wildlife and enjoy tranquil walks in this expansive park, providing an ideal setting for family outings near Windlesham.
Adult Activities
- Golfing at Windlesham Golf Club: Enjoy a round of golf on this scenic course known for its challenging play and beautiful surroundings within the region.
- Walking and Cycling Trails: Explore the area's scenic countryside on well-maintained walking and cycling paths that showcase the natural beauty of this destination.
- Visit Windsor Great Park: Experience the tranquility of this expansive park, perfect for leisurely walks, picnics, or spotting local wildlife while staying nearby.
- Dining at Local Pubs and Restaurants: Indulge in authentic British cuisine at charming establishments here, offering a cozy atmosphere and regional specialties.
Windlesham Travel Tips
How Can You Make the Most of Your Stay?
- Explore local outdoor attractions: Take advantage of scenic walks and nature trails around Windlesham to fully experience the tranquility and natural beauty of this charming area.
- Visit nearby historical sites: Discover the rich heritage and history that surrounds your vacation rentals in the region to gain a deeper appreciation of this destination.
- Enjoy authentic regional cuisine: Dine at local eateries or prepare fresh ingredients in your rental kitchen to indulge in the flavors unique to this part of England.
- Plan day trips to popular destinations: Use your comfortable base here to venture out to nearby towns and scenic spots, making the most of your stay in this welcoming locale.
Transportation Options
- Windlesham Railway Station: This station offers convenient train services connecting you to major cities and towns across the region, making your travel to and from this area straightforward.
- Local Bus Services: Several bus routes operate throughout the area, providing accessible options for exploring nearby attractions and reaching neighboring communities.
- Taxis and Private Hire Vehicles: Reliable taxi services are available locally, offering comfortable and direct transportation tailored to your schedule within Windlesham and beyond.
- Car Rental Agencies: Multiple car rental options are accessible nearby, giving you the flexibility to explore the wider region at your own pace during your stay here.
Local Customs Options
- Traditional Punting on Local Waterways: You might experience the local custom of punting, a popular activity that reflects the area's leisurely and social spirit along nearby rivers.
- Sunday Morning Church Services: Participating in or observing Sunday services at historic churches highlights the region’s deep-rooted religious traditions and community bonds.
- Harvest Festivals and Markets: Engaging in seasonal harvest festivals and visiting local markets allows you to enjoy authentic regional produce and crafts.
- Celebration of Local Heritage Events: Attending traditional events dedicated to the area's history fosters a deeper connection to the region's cultural identity and customs.
Frequently Asked Questions About Windlesham?
1. What are the top vacation rentals in Windlesham?
There are a lot of options in Windlesham. If you plan on staying in the Windlesham area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windlesham:
- Stunning flat in quiet surroundings, 10 min walk to Ascot Racecourse
- CHOBHAM, Surrey. Spacious luxury mansion conversion Sleeps4/5
- Super Chic Apartment in Beautiful Sunninghill - Pass the Keys
- Beautiful 3 bed, 2 bath cottage with off road parking and storage.
- Cosy Home with beautiful views
- Luxury Ascot Indoor Heated Pool & Wellness Bubble Spa
- The Royal Paddock
- The Royal Paddock in Ascot
- Spacious 5 bed Sunninghill W/Drive - By Tempstay
- Newly Refurbished 3-Bedroom Home w/Free Parking
2. Which vacation homes in Windlesham are best for families?
If you are looking for a family-friendly vacation home in Windlesham, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Windlesham:
3. How many Rentbyowner vacation rentals are available in Windlesham?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 115 in the Windlesham area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windlesham.
4. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary by property; you should review the specific listing details or contact the property owner directly to understand the terms and any applicable fees.
5. How do I confirm the availability of my preferred vacation rental in this destination?
Availability can be checked directly through the listing on the website, where you can see real-time updates or reach out to the property owner for confirmation.
6. Are there any specific check-in or check-out procedures for staying here?
Check-in and check-out procedures are typically outlined in the property listing. If you have questions, contacting the owner can provide clarity and ensure a smooth arrival and departure.
7. What amenities are included in the vacation rentals in this region?
Amenities vary from property to property; details are provided in each listing. You may also contact the owner to confirm the availability of specific features during your stay.
8. Is there a minimum stay requirement for booking a vacation rental in this area?
Minimum stay requirements depend on the individual property. Be sure to review the listing details or ask the owner directly to confirm the length of stay needed.
Windlesham Top Rated Vacation Rentals
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Spa
- Pool
- Balcony/Terrace
ZA R10,570/Night
For 7 Nights ZA R73,980
606.37 ft²
36 Guests
69 Bedrooms
12 Bathrooms
Family Friendly
Hotel
- Private Pool
- Spa
- Fireplace/Heating
ZA R13,612/Night
For 7 Nights ZA R95,291
470.25 ft²
39 Guests
124 Bedrooms
16 Bathrooms
Ocean View
Resort
- Private Pool
- Oceanfront
- Hot Tub
ZA R6,337/Night
For 7 Nights ZA R44,362
ZA R2,184/Night
For 7 Nights ZA R15,285
215.28 ft²
23 Guests
126 Bedrooms
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Hot Tub
- Spa
ZA R2,295/Night
For 7 Nights ZA R16,057
