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Windlesham Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Windlesham vacation rentals

Private kitchen
Spacious flat in Hammersmith 15min from center

Apartment in Hammersmith

Spacious flat in Hammersmith 15min from center
$184 nightly
The price is $184
Dec 31 - Jan 1, 2026
Total with taxes and fees
Spacious flat in Hammersmith 15min from center
Fridge, microwave, oven, stovetop
2 Bed - Sleeps 6 - Free Parking

Apartment in Bracknell

2 Bed - Sleeps 6 - Free Parking
3.5 star property
10.0 out of 10, Exceptional, (1)
"Lovely apartment and had everything we needed. Good communication from the host. "
United Kingdom
Helen
$160 nightly
The price is $192
Dec 15 - Dec 16
Total with taxes and fees
2 Bed - Sleeps 6 - Free Parking
Fridge, microwave, stovetop, electric kettle
Cosy 1 Bedroom Apartment Private Access in Guildford

Apartment in Guildford

Cosy 1 Bedroom Apartment Private Access in Guildford
10.0 out of 10, Exceptional, (1)
"Great communication from the host. Clean efficient accommodation. Bus close by to get in to Guildford town centre "
United Kingdom
Frances
$142 nightly
The price is $142
Dec 12 - Dec 13
Total with taxes and fees
Cosy 1 Bedroom Apartment Private Access in Guildford
Full-size fridge, microwave, oven, stovetop
Kensington House by Solitaire Suites

Aparthotel in Slough

Kensington House by Solitaire Suites
3.0 star property
7.2 out of 10, Good, (20)
"Came down for a few days with wife and kids. Felt really safe within property and very welcoming. Had no issue's at all will be back hopefully."
United Kingdom
Charles
$100 nightly
The price is $120
Jan 9 - Jan 10, 2026
Total with taxes and fees
Kensington House by Solitaire Suites
Fridge, microwave, oven, stovetop
A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.

Cabin in Old Windsor

A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.
9.4 out of 10, Exceptional, (3)
"Had a great stay prior to our flight home. They had everything we needed including things for the kids (1 and 3)."
United States
Peyton T.
$171 nightly
The price is $171
Dec 13 - Dec 14
Total with taxes and fees
A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.
1 bedroom, WiFi
Nestled in a grand private estate, near woodlands, easy access London

Apartment in Coombe Hill

Nestled in a grand private estate, near woodlands, easy access London
10.0 out of 10, Exceptional, (2)
"The place was very clean and in a great area! Also the property owners were very responsive, helpful, and very hospitable. You can tell these two really care about your stay. Top place in London"
United States
Juan C.
$194 nightly
The price is $229
Dec 11 - Dec 12
Total with taxes and fees
Nestled in a grand private estate, near woodlands, easy access London
Exterior
Perfect for walkers, Goodwood, National Trust, Short Stay

Vacation Home in Bramshott Chase

Perfect for walkers, Goodwood, National Trust, Short Stay
9.6 out of 10, Exceptional, (4)
"This little gem was a perfect place for us to stay visiting devils Punchbowl for mountain biking. Thank you "
United Kingdom
Corinne H.
$148 nightly
The price is $148
Dec 11 - Dec 12
Total with taxes and fees
Perfect for walkers, Goodwood, National Trust, Short Stay
Interior
Cuckoo s Hideaway - From 75 Per Night

Apartment in Marlow

Cuckoo s Hideaway - From 75 Per Night
2.0 star property
10.0 out of 10, Exceptional, (4)
"The hideaway was perfect, we really enjoyed the garden and the quiet space. Conveniently located for local restaurants and activities."
United Kingdom
Tamara
$181 nightly
The price is $217
Dec 15 - Dec 16
Total with taxes and fees
Cuckoo s Hideaway - From 75 Per Night
Exterior
Spacious, light apartment sleeps up to four

Apartment in Cookham

Spacious, light apartment sleeps up to four
9.8 out of 10, Exceptional, (18)
"Beautifully refurbished property with very helpful hosts."
United Kingdom
Alexandra C.
$279 nightly
The price is $279
Dec 11 - Dec 12
Total with taxes and fees
Spacious, light apartment sleeps up to four
Fridge, microwave, oven, stovetop
HQ Aparthotel Farnborough

Aparthotel in Rushmoor District

HQ Aparthotel Farnborough
4.0 star property
9.0 out of 10, Wonderful, (448)
"The room is tidy and customer services is good in the hotel"
United Kingdom
Lewis
$85 nightly
The price is $102
Jan 4 - Jan 5, 2026
Total with taxes and fees
HQ Aparthotel Farnborough
View from room
Aparthotel Adagio London Brentford

Aparthotel in Brentford

Aparthotel Adagio London Brentford
4.0 star property
9.0 out of 10, Wonderful, (1199)
"Current favourite place to stay at, will be returning soon"
United States
Halima
$95 nightly
The price is $114
Dec 14 - Dec 15
Total with taxes and fees
Aparthotel Adagio London Brentford
Studio | Exterior
Beautiful 1-bed Studio in Uxbridge, London

Apartment in Hillingdon East

Beautiful 1-bed Studio in Uxbridge, London
3.0 star property
10.0 out of 10, Exceptional, (1)
"Pulito e comodo ai servizi per andare in centro a Londra "
Italy
Diana Alexandra
$131 nightly
The price is $157
Jan 9 - Jan 10, 2026
Total with taxes and fees
Beautiful 1-bed Studio in Uxbridge, London
Exterior detail
Willow Court Farm

Apartment in Windsor

Willow Court Farm
4.0 star property
10.0 out of 10, Exceptional, (199)
"Wonderful place ideal for families "
United Kingdom
Zoe
$145 nightly
The price is $175
Dec 11 - Dec 12
Total with taxes and fees
Willow Court Farm
Private kitchen
Double room with private bathroom

Vacation Home in Hounslow Heath

Double room with private bathroom
8.0 out of 10, Very Good, (4)
"Wonderful stay, amazing nights sleep"
United Kingdom
Tej
$128 nightly
The price is $128
Dec 11 - Dec 12
Total with taxes and fees
Double room with private bathroom
Cottage | Balcony
Groomes Country House

Cottage in Bordon

Groomes Country House
3.5 star property
$3,279 nightly
The price is $3,935
Dec 14 - Dec 15
Total with taxes and fees
Groomes Country House
Fridge, microwave, oven, stovetop
Cosy Flat in Sutton with Parking free

Apartment in SUTTON

Cosy Flat in Sutton with Parking free
9.0 out of 10, Wonderful, (8)
"A wonderful place to stay! Communication started off rocky due to technical issues, but host was super kind and patient about it! This place is so close to a station, which makes it perfect for any first time travellers. Plenty of shops and restaurants are nearby, but be mindful when ordering Uber or delivery, as the address can be confusing on Google Maps. I stayed for a month here, and it felt like home. Definitely a great place to stay at if you're a first time traveler like me!"
United States
Janice F.
$138 nightly
The price is $138
Dec 16 - Dec 17
Total with taxes and fees
Cosy Flat in Sutton with Parking free
Two Bedroom Apartment - Balcony | Living area | 40-inch flat-screen TV with digital channels
Staines Riverside by Charles Hope

Apartment in Staines

Staines Riverside by Charles Hope
4.0 star property
7.6 out of 10, Good, (13)
"Property very clean and in a great location. Little trouble with the front door but cleaner showed us the knack then it easy. Would stay again"
United Kingdom
Vikki
$123 nightly
The price is $147
Jan 4 - Jan 5, 2026
Total with taxes and fees
Staines Riverside by Charles Hope
Apartment | 2 bedrooms
Central Modern Flat Sleeps 6 - Dedicated Parking - From 125 Per Night

Apartment in Henley-on-Thames

Central Modern Flat Sleeps 6 - Dedicated Parking - From 125 Per Night
2.0 star property
10.0 out of 10, Exceptional, (1)
$350 nightly
The price is $350
Jan 4 - Jan 5, 2026
Total with taxes and fees
Central Modern Flat Sleeps 6 - Dedicated Parking - From 125 Per Night
Apartment, 1 Bedroom | Private kitchen | Full-size fridge, microwave, oven, stovetop
Imperial Court by Viridian Apartments

Apartment in Maidenhead

Imperial Court by Viridian Apartments
4.0 star property
7.2 out of 10, Good, (7)
"Great location near Maidenhead town centre"
United Kingdom
Roaa
$140 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
Imperial Court by Viridian Apartments
Property grounds
Beautiful Rural Barn - stunning interior

Vacation Home in Ockley

Beautiful Rural Barn - stunning interior
10.0 out of 10, Exceptional, (14)
"A gorgeous little barn which was perfect for a quiet, relaxing getaway. Love the location and easy walks out into the countryside. The barn is super clean with great facilities - couldn’t ask for any more. "
United Kingdom
Suzanne M.
$198 nightly
The price is $198
Dec 11 - Dec 12
Total with taxes and fees
Beautiful Rural Barn - stunning interior
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windlesham Hotel Reviews

Leonardo London Heathrow Airport

Leonardo London Heathrow Airport

10/10 Excellent
"Helpful front desk, friendly restaurant staff, and comfortable facilities. Always our first choice for our stays in London. "
James 1-night trip
Posted 21 hours ago
Leonardo London Heathrow Airport

Find out more about Windlesham

Everything you need to know about Windlesham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windlesham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windlesham vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windlesham vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windlesham. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Windlesham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $62 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windlesham rentals

At Expedia, we put the best Windlesham vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windlesham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windlesham vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windlesham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Windlesham?

Yes, you can find vacation rentals where you'll be just 6.4 mi (10.4 km) from LEGOLAND® Windsor, offering you a more secluded option to escape the hustle and bustle.

What's the top vacation rental that Windlesham has to offer?

Spacious 6 Bed House in Wembley: You might want to consider this vacation rental near Windlesham, which comes with WiFi so you can feel at home during your trip. It has 6 bedrooms as well as a kitchenette with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family.

What’s there to see and do in Windlesham?

Explore the area and family-friendly sights such as LEGOLAND® Windsor, or get out into nature at a spot like Virginia Water. Sunningdale Golf Club and Ascot Racecourse are a couple of places you'll find in the larger area.

What’s a vacation rental in Windlesham like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Windlesham. Vacation rentals feature amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a small group gathering.