115+ Rental Villas and Private Getaways in Windlesham |
Windlesham Villa Rentals
Apartment
10.0Exceptional
(22 Reviews)
1 Bedroom
1 Bath
2 Guests
538 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $149/Night
7 Nights - US $1,046
Apartment
- Ascot
- ·
- Sunninghill
- 0.39 mi to center
10.0Exceptional
(4 Reviews)
2 Bedrooms
1 Bath
6 Guests
796.53 ft²
- Fireplace/Heating
View- Parking
Internet
US $270/Night
7 Nights - US $1,893
Cottage
- Ascot
- ·
- Sunningdale
- 0.60 mi to center
1 Bedroom
1 Bath
Hot Tub- Fireplace/Heating
Pool- Balcony/Terrace
Unlock the Best Price
House
- Ascot
- ·
- Sunninghill
- 0.55 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $339/Night
7 Nights - US $2,374
Apartment
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
2 Guests
430.56 ft²
- Balcony/Terrace
- View
- Parking
- Internet
US $127/Night
7 Nights - US $892
House
10.0Exceptional
(1 Review)
1 Bedroom
3 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $666/Night
7 Nights - US $4,663
House
- Ascot
- ·
- Sunninghill
- 0.18 mi to center
10.0Exceptional
(1 Review)
5 Bedrooms
2 Baths
9 Guests
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Kitchen
US $538/Night
7 Nights - US $3,764
House
10.0Exceptional
(1 Review)
3 Bedrooms
1 Bath
6 Guests
988 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $320/Night
7 Nights - US $2,241
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
Spa- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $240/Night
7 Nights - US $1,681
Luxury Places to Stay in Windlesham
Over 106+ Luxury Places to Stay in or Near Windlesham
House
- Ascot
- ·
- Sunningdale
- 0.60 mi to center
7 Bedrooms
6 Baths
14 Guests
2045.14 ft²
- Pool
- View
- Parking
- Internet
US $3,721/Night
7 Nights - US $26,047
Cottage
- Ascot
- ·
- Sunningdale
- 0.43 mi to center
7 Bedrooms
4 Baths
14 Guests
2045 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $3,346/Night
7 Nights - US $23,419
House
- England
- ·
- Windlesham
- 0.11 mi to center
5 Bedrooms
7 Baths
12 Guests
Private Pool- Hot Tub
- Fireplace/Heating
- Pool
US $3,253/Night
7 Nights - US $22,773
House
- Ascot
- ·
- Sunningdale
- 0.78 mi to center
5 Bedrooms
3 Baths
10 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $2,861/Night
7 Nights - US $20,028
House
- Ascot
- ·
- Sunningdale
- 1.46 mi to center
6 Bedrooms
5 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $2,634/Night
7 Nights - US $18,437
House
- Ascot
- ·
- Sunningdale
- 0.63 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
3 Baths
10 Guests
6372.23 ft²
- Private Pool
Oceanfront- Hot Tub
- Spa
US $1,943/Night
7 Nights - US $13,601
House
- Ascot
- ·
- Sunningdale
- 0.71 mi to center
4 Bedrooms
3 Baths
8 Guests
225 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $1,410/Night
7 Nights - US $9,872
House
- Ascot
- ·
- Sunninghill
- 0.37 mi to center
4 Bedrooms
4 Baths
8 Guests
- Fireplace/Heating
- Internet
Child Friendly
Laundry
US $808/Night
7 Nights - US $5,653
House
- Ascot
- ·
- Sunninghill
- 0.37 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
7 Guests
2292.71 ft²
- Fireplace/Heating
- View
- Parking
- Internet
US $788/Night
7 Nights - US $5,518
Top-Rated Villas with a Pool in Windlesham
Over 8+ Top-Rated Private Villas with a Pool in or Near Windlesham
Hotel
- Ascot
- ·
- Sunningdale
- 1.07 mi to center
9.6Exceptional
(202 Reviews)
1 Bath
- Spa
- Pool
- Balcony/Terrace
Breakfast
US $752/Night
7 Nights - US $5,266
Hotel
- Ascot
- ·
- Sunningdale
- 1.20 mi to center
9.4Exceptional
(326 Reviews)
13 Baths
588.7 ft²
- Private Pool
- Spa
- Fireplace/Heating
- Pool
US $669/Night
7 Nights - US $4,681
Resort
8.5Fabulous
(188 Reviews)
16 Baths
39 Guests
470.25 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Spa
US $386/Night
7 Nights - US $2,702
Hotel
- Ascot
- ·
- Sunninghill
- 0.22 mi to center
7.8Very Good
(888 Reviews)
1 Bath
- Spa
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $138/Night
7 Nights - US $967
Hotel
- Ascot
- ·
- Sunninghill
- 0.20 mi to center
7.3Very Good
(2582 Reviews)
1 Bath
215.28 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
US $185/Night
7 Nights - US $1,298
New
House
- Ascot
- ·
- Sunninghill
- 0.45 mi to center
4 Bedrooms
4 Baths
8 Guests
3003.13 ft²
- Oceanfront
- Spa
- Fireplace/Heating
- Pool
US $522/Night
7 Nights - US $3,655
House
- Ascot
- ·
- Sunningdale
- 0.59 mi to center
10 Bedrooms
10 Baths
16 Guests
- Private Pool
- Pool
- Kitchen
Air Conditioner
US $2,986/Night
7 Nights - US $20,901
House
7 Bedrooms
5 Baths
16 Guests
- Private Pool
- Pool
- Kitchen
- Air Conditioner
US $2,553/Night
7 Nights - US $17,870
Pet-Friendly Villas in Windlesham
Over 35+ Pet-Friendly Private Villas in or Near Windlesham
House
- Ascot
- ·
- Sunningdale
- 0.56 mi to center
8.0Excellent
(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $363/Night
7 Nights - US $2,541
New
House
10.0Exceptional
(1 Review)
4 Bedrooms
6 Baths
12 Guests
699.65 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
US $257/Night
7 Nights - US $1,802
Cottage
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Pet Friendly
- Internet
- Child Friendly
US $659/Night
7 Nights - US $4,613
House
9.0Exceptional
(11 Reviews)
3 Bedrooms
1 Bath
6 Guests
990.28 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
US $397/Night
7 Nights - US $2,782
House
- Ascot
- ·
- Sunningdale
- 0.40 mi to center
3 Bedrooms
1 Bath
6 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Internet
US $466/Night
7 Nights - US $3,263
House
3 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $417/Night
7 Nights - US $2,922
Ski Chalet
4 Bedrooms
2 Baths
7 Guests
1615 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $339/Night
7 Nights - US $2,372
Ski Chalet
- Ascot
- ·
- Sunningdale
- 0.32 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
7 Guests
1507 ft²
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Child Friendly
US $302/Night
7 Nights - US $2,117
Apartment
- Ascot
- ·
- Sunninghill
- 0.39 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
3 Guests
646 ft²
- Pet Friendly
- Kitchen
- Internet
- Child Friendly
US $134/Night
7 Nights - US $937
Large Private Villas in Windlesham
Over 10+ Large Villas in or Near Windlesham for Groups and Families
House
- Ascot
- ·
- Sunninghill
- 0.22 mi to center
9.8Exceptional
(15 Reviews)
7 Bedrooms
6 Baths
16 Guests
5500 ft²
- Hot Tub
- Fireplace/Heating
Ocean View- Balcony/Terrace
US $2,355/Night
7 Nights - US $16,485
House
- Ascot
- ·
- Sunninghill
- 0.24 mi to center
8.9Fabulous
(11 Reviews)
5 Bedrooms
2 Baths
9 Guests
- View
- Parking
- Internet
- Child Friendly
US $495/Night
7 Nights - US $3,468
House
5.0Average
(1 Review)
5 Bedrooms
4 Baths
14 Guests
1292 ft²
- Kitchen
- Internet
- Child Friendly
- Laundry
US $365/Night
7 Nights - US $2,557
Villa
- Ascot
- ·
- Sunningdale
- 0.47 mi to center
7.8Very Good
(10 Reviews)
3 Bedrooms
2 Baths
6 Guests
129.17 ft²
- View
- Pet Friendly
- Parking
- Internet
US $362/Night
7 Nights - US $2,533
House
2.0Average
(1 Review)
6 Bedrooms
4 Baths
14 Guests
1076 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Internet
US $404/Night
7 Nights - US $2,830
US $2,142/Night
7 Nights - US $14,995
House
- England
- ·
- Lightwater
- 0.10 mi to center
5 Bedrooms
5 Baths
8 Guests
1937 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $1,110/Night
7 Nights - US $7,770
House
6 Bedrooms
5 Baths
12 Guests
- Balcony/Terrace
- Kitchen
- Child Friendly
- Laundry
US $998/Night
7 Nights - US $6,983
Cottage
- Ascot
- ·
- Sunninghill
- 0.38 mi to center
5 Bedrooms
5 Baths
11 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Internet
US $680/Night
7 Nights - US $4,758
Wheelchair Accessible Holiday Homes in Windlesham
Over 6+ Wheelchair Accessible Villas and Holiday Homes in or Near Windlesham
Apartment
- Ascot
- ·
- Sunningdale
- 0.57 mi to center
8.0Excellent
(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $487/Night
7 Nights - US $3,410
Hotel
9.2Exceptional
(769 Reviews)
4 Baths
236.81 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
US $159/Night
7 Nights - US $1,114
Hotel
6.0Good
(1 Review)
1 Bath
- Breakfast
- Parking
- Internet
- Child Friendly
US $117/Night
7 Nights - US $819
Apartment
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
4 Guests
550 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Internet
US $110/Night
7 Nights - US $771
Hotel
8.6Fabulous
(520 Reviews)
14 Baths
364.44 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $278/Night
7 Nights - US $1,945
Apartment
- Ascot
- ·
- Sunningdale
- 1.19 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $716/Night
7 Nights - US $5,015
Windlesham Villas, Airbnb and Holiday Homes Under $200
Over 21+ Windlesham Private Villas, Airbnb and Holiday Homes Under $200
House
- Ascot
- ·
- Sunninghill
- 0.39 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
398 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Internet
US $175/Night
7 Nights - US $1,222
Apartment
- Ascot
- ·
- Sunninghill
- 0.08 mi to center
9.5Exceptional
(70 Reviews)
1 Bedroom
1 Bath
2 Guests
398.26 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Parking
US $102/Night
7 Nights - US $714
Hotel
9.6Exceptional
(273 Reviews)
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Breakfast
- Kitchen
US $181/Night
7 Nights - US $1,269
House
- Ascot
- ·
- Sunninghill
- 0.29 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Child Friendly
Security/Safety
US $145/Night
7 Nights - US $1,018
House
- Ascot
- ·
- Sunninghill
- 0.39 mi to center
9.2Exceptional
(9 Reviews)
1 Bedroom
1 Bath
6 Guests
398.26 ft²
- Fireplace/Heating
- Parking
- Internet
- Child Friendly
US $152/Night
7 Nights - US $1,064
Cottage
- Ascot
- ·
- Sunninghill
- 0.36 mi to center
8.0Excellent
(1 Review)
2 Bedrooms
1 Bath
4 Guests
602 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $152/Night
7 Nights - US $1,063
Apartment
- England
- ·
- Windlesham
- 0.41 mi to center
2 Bedrooms
1 Bath
5 Guests
- Kitchen
- Child Friendly
- Laundry
TV
US $187/Night
7 Nights - US $1,306
House
2 Bedrooms
1 Bath
4 Guests
700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $161/Night
7 Nights - US $1,129
Apartment
- England
- ·
- Windlesham
- 0.41 mi to center
2 Bedrooms
1 Bath
5 Guests
- Kitchen
- Child Friendly
- Laundry
- TV
US $142/Night
7 Nights - US $995
Instantly Bookable Villa Rentals in Windlesham
Over 29+ Instantly Bookable Private Villas in or Near Windlesham
House
4.0Average
(1 Review)
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $476/Night
7 Nights - US $3,332
House
3 Bedrooms
3 Baths
6 Guests
1195 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $351/Night
7 Nights - US $2,456
House
- England
- ·
- Windlesham
- 0.33 mi to center
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Internet
US $325/Night
7 Nights - US $2,278
Apartment
- Ascot
- ·
- Sunningdale
- 0.57 mi to center
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Internet
US $291/Night
7 Nights - US $2,037
Apartment
2 Bedrooms
2 Baths
4 Guests
807 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Internet
US $274/Night
7 Nights - US $1,916
Apartment
- Ascot
- ·
- Sunninghill
- 0.39 mi to center
2 Bedrooms
1 Bath
4 Guests
797 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $269/Night
7 Nights - US $1,884
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Internet
US $241/Night
7 Nights - US $1,686
House
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $508/Night
7 Nights - US $3,559
Apartment
- Ascot
- ·
- Sunningdale
- 0.40 mi to center
3 Bedrooms
1 Bath
5 Guests
17222 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $1,102/Night
7 Nights - US $7,713
Book a Last Minute Place to Stay in Windlesham
About Windlesham Vacation Rentals
There are more than 115 incredible getaway rentals that are available in Windlesham. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in Windlesham.
BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in Windlesham, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in Windlesham. Places to stay near Windlesham are 846.7 ft² on average, with prices averaging US $668 a night.
BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Windlesham. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.
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Top Private Villas, Resorts, and Rentals in Windlesham
| Type | Count |
|---|---|
| Vacation Homes | 61 |
| Holiday Apartments | 33 |
| Cottages | 5 |
| Ski Chalet Rentals | 4 |
| Villas | 2 |
Use these Quick Filters to Find a Vacation Rental in Windlesham
★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Windlesham with BedroomVillas.
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
Stay Near Windlesham's Top Attractions
A Large Selection of Villas and Vacation Rentals from Around the World Windlesham's Research Top Attractions For Your Vacation
Frequently Asked Questions About Windlesham?
What are the top hotels or resorts in Windlesham?
We provide an array of great vacation destinations in Windlesham. If you are looking to stay in or around the Windlesham area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Windlesham:
- Stunning flat in quiet surroundings, 10 min walk to Ascot Racecourse
- Super Chic Apartment in Beautiful Sunninghill - Pass the Keys
- Cosy Home with beautiful views
- Luxury Ascot Indoor Heated Pool & Wellness Bubble Spa
- Beautiful 3 bed, 2 bath cottage with off road parking and storage.
- Magnolia Lodge - 4 Beds Fabulous Garden Parking
- The Royal Paddock in Ascot
- The Royal Paddock
- Spacious 5 bed Sunninghill W/Drive - By Tempstay
- Newly Refurbished 3-Bedroom Home w/Free Parking
Which hotel or resort in Windlesham is best for families?
Searching for a family-friendly getaway in Windlesham? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.
- Magnolia Lodge - 4 Beds, Fabulous Garden, Parking
- The Royal Paddock
- CHOBHAM, Surrey. Spacious luxury mansion conversion Sleeps4/5
How many hotels, resorts, or rentals are available in Windlesham?
BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 115 in the Windlesham area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in Windlesham.
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