115+ Private Villas and Holiday Rentals in Windlesham |
Windlesham Holiday Rentals
10.0
Exceptional
(22 Reviews)
538 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $149/Night
For 7 Nights US $1,046
10.0
Exceptional
(4 Reviews)
- Ascot
- Sunninghill
- 0.39 mi to center
796.53 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- View
- Parking
US $270/Night
For 7 Nights US $1,893
New
- Ascot
- Sunningdale
- 0.60 mi to center
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Hot Tub
- Fireplace/Heating
- Pool
Unlock the Best Price
10.0
Exceptional
(6 Reviews)
5 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $353/Night
For 7 Nights US $2,468
10.0
Exceptional
(2 Reviews)
430.56 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Balcony/Terrace
- View
- Parking
US $127/Night
For 7 Nights US $892
10.0
Exceptional
(2 Reviews)
- Ascot
- Sunninghill
- 0.55 mi to center
5 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $327/Night
For 7 Nights US $2,287
10.0
Exceptional
(1 Review)
6 Guests
1 Bedroom
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $683/Night
For 7 Nights US $4,779
10.0
Exceptional
(1 Review)
- Ascot
- Sunninghill
- 0.18 mi to center
9 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $448/Night
For 7 Nights US $3,138
10.0
Exceptional
(1 Review)
988 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $393/Night
For 7 Nights US $2,754
Luxury Holiday Rentals in Windlesham
Over 106+ Luxury Holiday Rentals in or Near Windlesham
New
- Ascot
- Sunningdale
- 0.60 mi to center
2045.14 ft²
14 Guests
7 Bedrooms
6 Bathrooms
Family Friendly
House
- Pool
- View
- Parking
US $3,721/Night
For 7 Nights US $26,047
New
- England
- Windlesham
- 0.11 mi to center
12 Guests
5 Bedrooms
7 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $3,253/Night
For 7 Nights US $22,773
New
- Ascot
- Sunningdale
- 0.43 mi to center
2045 ft²
14 Guests
7 Bedrooms
4 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $3,250/Night
For 7 Nights US $22,748
New
- Ascot
- Sunningdale
- 0.78 mi to center
10 Guests
5 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
US $2,982/Night
For 7 Nights US $20,875
New
- Ascot
- Sunningdale
- 1.46 mi to center
12 Guests
6 Bedrooms
5 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $2,767/Night
For 7 Nights US $19,366
10.0
Exceptional
(1 Review)
- Ascot
- Sunningdale
- 0.63 mi to center
6372.23 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
US $1,423/Night
For 7 Nights US $9,962
New
- Ascot
- Sunningdale
- 0.40 mi to center
17222.26 ft²
5 Guests
3 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- Breakfast
- Pet Friendly
US $1,075/Night
For 7 Nights US $7,528
10.0
Exceptional
(1 Review)
6 Guests
3 Bedrooms
3 Bathrooms
Free Cancellation
House
- Parking
- Internet
- Child Friendly
US $921/Night
For 7 Nights US $6,450
9.4
Exceptional
(276 Reviews)
- Ascot
- Sunningdale
- 1.20 mi to center
606.37 ft²
12 Bathrooms
Family Friendly
Hotel
- Private Pool
- Spa
- Fireplace/Heating
US $829/Night
For 7 Nights US $5,804
Top-Rated Holiday Rentals with a Pool in Windlesham
Over 6+ The Best Private Villas and Holiday Rentals in Windlesham with a Pool
9.6
Exceptional
(195 Reviews)
- Ascot
- Sunningdale
- 1.07 mi to center
1 Bathroom
Family Friendly
Hotel
- Spa
- Pool
- Balcony/Terrace
US $644/Night
For 7 Nights US $4,506
8.6
Fabulous
(210 Reviews)
470.25 ft²
39 Guests
16 Bathrooms
Ocean View
Resort
- Private Pool
- Oceanfront
- Hot Tub
US $386/Night
For 7 Nights US $2,702
7.8
Very Good
(857 Reviews)
- Ascot
- Sunninghill
- 0.22 mi to center
1 Bathroom
Couples Retreat
Hotel
- Spa
- Fireplace/Heating
- Pool
US $133/Night
For 7 Nights US $931
7.4
Very Good
(2884 Reviews)
- Ascot
- Sunninghill
- 0.20 mi to center
215.28 ft²
1 Bathroom
Family Friendly
Hotel
- Private Pool
- Hot Tub
- Spa
US $140/Night
For 7 Nights US $978
New
- Ascot
- Sunningdale
- 0.59 mi to center
16 Guests
10 Bedrooms
10 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Kitchen
US $2,986/Night
For 7 Nights US $20,901
New
16 Guests
7 Bedrooms
5 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Kitchen
US $2,553/Night
For 7 Nights US $17,870
Pet-Friendly Holiday Rentals in Windlesham
Over 34+ Pet-Friendly Holiday Rentals in or Near Windlesham
8.0
Excellent
(1 Review)
- Ascot
- Sunningdale
- 0.56 mi to center
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $363/Night
For 7 Nights US $2,541
9.0
Exceptional
(11 Reviews)
990.28 ft²
6 Guests
1 Bedroom
1 Bathroom
Free Cancellation
House
- Fireplace/Heating
- View
- Pet Friendly
US $397/Night
For 7 Nights US $2,782
New
8 Guests
3 Bedrooms
1 Bathroom
Pet Friendly
Cottage
- Fireplace/Heating
- Pet Friendly
- Internet
US $629/Night
For 7 Nights US $4,406
8.7
Fabulous
(6 Reviews)
- Ascot
- Sunningdale
- 0.47 mi to center
129.17 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Villa
- View
- Pet Friendly
- Parking
US $362/Night
For 7 Nights US $2,533
New
5 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $418/Night
For 7 Nights US $2,925
New
- Ascot
- Sunningdale
- 0.40 mi to center
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $405/Night
For 7 Nights US $2,838
New
1615 ft²
7 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Ski Chalet
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $364/Night
For 7 Nights US $2,545
10.0
Exceptional
(2 Reviews)
- Ascot
- Sunningdale
- 0.32 mi to center
1507 ft²
7 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
Ski Chalet
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $302/Night
For 7 Nights US $2,117
10.0
Exceptional
(1 Review)
- Ascot
- Sunninghill
- 0.39 mi to center
646 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Pet Friendly
- Kitchen
- Internet
US $134/Night
For 7 Nights US $937
Large Holiday Rentals and Private Villas in Windlesham
Over 10+ Large Holiday Rentals and Private Villas in or Near Windlesham
9.8
Exceptional
(15 Reviews)
- Ascot
- Sunninghill
- 0.22 mi to center
5500 ft²
16 Guests
7 Bedrooms
6 Bathrooms
Ocean View
House
- Hot Tub
- Fireplace/Heating
- Ocean View
US $2,355/Night
For 7 Nights US $16,485
9.4
Exceptional
(9 Reviews)
- Ascot
- Sunninghill
- 0.24 mi to center
9 Guests
5 Bedrooms
2 Bathrooms
Free Cancellation
House
- View
- Parking
- Internet
US $495/Night
For 7 Nights US $3,468
5.0
Average
(1 Review)
1292 ft²
14 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Kitchen
- Internet
- Child Friendly
US $365/Night
For 7 Nights US $2,557
New
10 Guests
3 Bedrooms
5 Bathrooms
Family Friendly
House
- Fireplace/Heating
- View
- Pet Friendly
US $257/Night
For 7 Nights US $1,802
2.0
Average
(1 Review)
1076 ft²
14 Guests
6 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $404/Night
For 7 Nights US $2,830
New
- Ascot
- Sunningdale
- 0.31 mi to center
14 Guests
8 Bedrooms
6 Bathrooms
Family Friendly
Villa
- Child Friendly
US $2,142/Night
For 7 Nights US $14,995
New
- England
- Lightwater
- 0.10 mi to center
1937 ft²
8 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $1,110/Night
For 7 Nights US $7,770
New
12 Guests
6 Bedrooms
5 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Kitchen
- Child Friendly
US $998/Night
For 7 Nights US $6,983
New
- Ascot
- Sunninghill
- 0.38 mi to center
11 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $680/Night
For 7 Nights US $4,758
Wheelchair Accessible Holiday Homes in Windlesham
Over 6+ Wheelchair Accessible Holiday Homes in or Near Windlesham
8.0
Excellent
(1 Review)
- Ascot
- Sunningdale
- 0.57 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $516/Night
For 7 Nights US $3,611
9.2
Exceptional
(769 Reviews)
236.81 ft²
4 Bathrooms
Free Cancellation
Hotel
- Fireplace/Heating
- Balcony/Terrace
- View
US $159/Night
For 7 Nights US $1,114
6.0
Good
(1 Review)
1 Bathroom
Couples Retreat
Hotel
- Breakfast
- Parking
- Internet
US $102/Night
For 7 Nights US $717
10.0
Exceptional
(5 Reviews)
550 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $110/Night
For 7 Nights US $771
8.6
Fabulous
(519 Reviews)
364.44 ft²
14 Bathrooms
Family Friendly
Hotel
- Fireplace/Heating
- Balcony/Terrace
- View
US $278/Night
For 7 Nights US $1,945
10.0
Exceptional
(1 Review)
- Ascot
- Sunningdale
- 1.19 mi to center
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $716/Night
For 7 Nights US $5,015
Windlesham Private Villas and Holiday Homes Under $200
Over 23+ Windlesham Private Villas and Holiday Homes Under $200
10.0
Exceptional
(1 Review)
- Ascot
- Sunninghill
- 0.39 mi to center
398 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $147/Night
For 7 Nights US $1,027
9.7
Exceptional
(65 Reviews)
- Ascot
- Sunninghill
- 0.08 mi to center
398.26 ft²
2 Guests
1 Bedroom
1 Bathroom
Apartment
- Fireplace/Heating
- Balcony/Terrace
- View
US $102/Night
For 7 Nights US $714
9.8
Exceptional
(271 Reviews)
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
US $171/Night
For 7 Nights US $1,197
10.0
Exceptional
(1 Review)
- Ascot
- Sunninghill
- 0.29 mi to center
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
House
- Child Friendly
- Security/Safety
US $145/Night
For 7 Nights US $1,018
8.6
Fabulous
(7 Reviews)
- Ascot
- Sunninghill
- 0.39 mi to center
398.26 ft²
6 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Parking
- Internet
US $152/Night
For 7 Nights US $1,064
New
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $198/Night
For 7 Nights US $1,386
New
- Ascot
- Sunninghill
- 0.39 mi to center
797 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $193/Night
For 7 Nights US $1,352
8.0
Excellent
(1 Review)
- Ascot
- Sunninghill
- 0.36 mi to center
602 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $152/Night
For 7 Nights US $1,063
New
- England
- Windlesham
- 0.41 mi to center
5 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Kitchen
- Child Friendly
- Laundry
US $187/Night
For 7 Nights US $1,306
Instantly Bookable Holiday Homes in Windlesham
Over 29+ Instantly Bookable Holiday Homes in or Near Windlesham
10.0
Exceptional
(1 Review)
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Spa
- Fireplace/Heating
- Balcony/Terrace
US $259/Night
For 7 Nights US $1,816
4.0
Average
(1 Review)
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
US $301/Night
For 7 Nights US $2,110
New
1195 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $335/Night
For 7 Nights US $2,343
New
- Ascot
- Sunningdale
- 0.57 mi to center
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
US $333/Night
For 7 Nights US $2,329
New
- England
- Windlesham
- 0.33 mi to center
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
US $331/Night
For 7 Nights US $2,315
New
807 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Balcony/Terrace
- Kitchen
- Internet
US $260/Night
For 7 Nights US $1,821
10.0
Exceptional
(1 Review)
5 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $508/Night
For 7 Nights US $3,559
New
- Ascot
- Sunningdale
- 0.40 mi to center
17222 ft²
5 Guests
3 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $1,102/Night
For 7 Nights US $7,713
New
- England
- Windlesham
- 0.76 mi to center
2756 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $763/Night
For 7 Nights US $5,338
Book a Last Minute Place to Stay in Windlesham
About Casai's Private Villas and Holiday Rentals in Windlesham
Discover more than 115 vacation rentals available in Windlesham. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Windlesham.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Windlesham, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Windlesham. On average, places to stay near Windlesham offer 959.64 ft², with nightly prices averaging US $660.
With Casai, finding and comparing holiday rentals in Windlesham is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Show more
Show less
Top Accommodation Types in Windlesham
| Type | Count |
|---|---|
| Vacation Homes | 59 |
| Holiday Apartments | 35 |
| Cottages | 5 |
| Villas | 2 |
Use these Quick Filters to Find a Holiday Rental in Windlesham
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Windlesham.
Weather in Windlesham, GB
View the weather forecast for Windlesham before booking your Windlesham Vacation Rentals to confirm your best time to go.
December - February
High 43°F Low 32°F
March - May
High 61°F Low 36°F
June - August
High 63°F Low 48°F
September - November
High 58°F Low 35°F
Top Attractions Around Windlesham, GB
Casai offers a large selection of top attractions around Windlesham . Research things to do on your vacation before you visit Windlesham.
Frequently Asked Questions About Windlesham?
What are the top holiday rentals in Windlesham?
With numerous options available in Windlesham, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday 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
Which holiday homes in Windlesham are best for families?
If you're searching for a family-friendly holiday home in Windlesham, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Windlesham:
- Hills End Cottage – Golf Course Views, Ascot
- 3 Bed 2 Bath Cottage with private parking and garage
- Magnolia Lodge - 4 Beds, Fabulous Garden, Parking
How many Casai.com holiday rentals are available in Windlesham?
As of 2026, Casai boasts over 115 properties listed in the Windlesham area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Windlesham.
People Also Ask
Finding the best prices in Windlesham
Map
