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Winnersh Holiday Rentals

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Our top choices for Winnersh holiday rentals

Cottage in Bordon

Groomes Country House
3.5 star property
The price is AU$6,064
includes taxes & fees
3 Jan - 4 Jan 2026
Groomes Country House

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
The price is AU$290
includes taxes & fees
5 Jan - 6 Jan 2026
2 Bed - Sleeps 6 - Free Parking

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
The price is AU$263
includes taxes & fees
4 Jan - 5 Jan 2026
Willow Court Farm

Aparthotel in Rushmoor District

HQ Aparthotel Farnborough
4.0 star property
9.0 out of 10, Wonderful, (449)
"The room is tidy and customer services is good in the hotel"
United Kingdom
Lewis
The price is AU$138
includes taxes & fees
4 Jan - 5 Jan 2026
HQ Aparthotel Farnborough

Apartment in Reading City Centre

VICTORIA HOUSE by Aeria Apartments
4.0 star property
7.8 out of 10, Good, (40)
"As always, we love Victoria while traveling to UK."
United States
Trailer
VICTORIA HOUSE by Aeria Apartments
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
The price is AU$218
includes taxes & fees
2 Jan - 3 Jan 2026
Cosy 1 Bedroom Apartment Private Access in Guildford

Apartment in Rushmoor District

Blue sky at Wallis square
4.0 star property
9.2 out of 10, Wonderful, (86)
"Bigger than expected. Nice place to stay for a few days."
Netherlands
Avelin
Blue sky at Wallis square

Aparthotel in Reading City Centre

PREMIER SUITES Reading
4.0 star property
8.8 out of 10, Excellent, (158)
"Excellent location . Pleasant staff. Clean but the room has a weird chemical smell . The bedroom is very small while the living area is unnecessarily big !! The lift was out order throughout our 9-day stay . "
United States
Raja
The price is AU$179
includes taxes & fees
29 Dec - 30 Dec
PREMIER SUITES Reading
9.8 out of 10, Exceptional, (18)
"Beautifully refurbished property with very helpful hosts."
United Kingdom
Alexandra C.
The price is AU$427
includes taxes & fees
29 Dec - 30 Dec
Spacious, light apartment sleeps up to four
9.6 out of 10, Exceptional, (4)
"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.
The price is AU$261
includes taxes & fees
30 Dec - 31 Dec
A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.

Apartment in Staines Town Centre

Staines City Centre by Charles Hope
3.5 star property
8.8 out of 10, Excellent, (38)
"Good quality accommodation and great prices. Very convenient to amenities and transport "
United Kingdom
Alan
Staines City Centre by Charles Hope

Apartment in Woking

Oaklawn Serviced Apartments
3.5 star property
9.6 out of 10, Exceptional, (10)
"Host is amazing ! "
United States
Erin
The price is AU$300
includes taxes & fees
5 Jan - 6 Jan 2026
Oaklawn Serviced Apartments

Apartment in Reading

Ivory Lodge
4.0 star property
8.6 out of 10, Excellent, (11)
"Looked beautiful on our arrival, superbly clean and luxurious. Manager was excellent in communication and handled any issues very fast and efficiently. "
United Kingdom
Dominee
The price is AU$357
includes taxes & fees
5 Jan - 6 Jan 2026
Ivory Lodge
10.0 out of 10, Exceptional, (1)
"Thoroughly enjoyed our stay at this beautiful, cozy, warm Ariel cottage. Woodland area for walks nearby golf course, dogs welcome although we did not take any pets but so suitable for your furry friends.Jake very welcoming, thankyou so much"
United Kingdom
Heidi C.
The price is AU$384
includes taxes & fees
2 Jan - 3 Jan 2026
Charming Cottage within Ancient Woodland Forest
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
Staines Riverside by Charles Hope
10.0 out of 10, Exceptional, (2)
"Great host with excellent communication and the property was as described. Perfect for our needs, thank you"
United Kingdom
Emma A.
The price is AU$301
includes taxes & fees
3 Jan - 4 Jan 2026
Central Spacious apartment located in the heart of it all!
3.0 star property
8.0 out of 10, Very good, (1)
"Property is in a great location. Cottage is unique and quaint. Floors sloping upstairs and very squeaky. Beds very comfortable. Paperwork from owner was overwhelming and too much. "
United Kingdom
Alison
The price is AU$444
includes taxes & fees
4 Jan - 5 Jan 2026
1400 Cottage An Enchanting Unique Stay - From 120 Per Night
10.0 out of 10, Exceptional, (3)
"A truly great little flat. The place was very clean and well-maintained. It had excellent facilities and it was clear that a lot of thought and attention had been given to the small details, which made for a very comfortable and pleasant stay."
United Kingdom
Katie W.
The price is AU$484
includes taxes & fees
30 Dec - 31 Dec
A new 3-bed flat with en-suite near Heathrow
3.0 star property
9.8 out of 10, Exceptional, (13)
"What an absolutely stunning apartment in a perfect location to explore Windsor. Spotlessly clean with everything you could possibly need for a few nights away. Even a Christmas tree which was a lovely surprise. Once we had a direct contact number for the property the communication was fantastic with check in details and instructions provided. Would 100% stay again in the future Thankyou "
United Kingdom
Corinne
Hampden Apartments - The Louis
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
The price is AU$282
includes taxes & fees
3 Jan - 4 Jan 2026
Kensington House by Solitaire Suites
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 Winnersh Hotel Reviews

Find out more about Winnersh

Everything you need to know about Winnersh holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winnersh holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Winnersh holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winnersh holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winnersh holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winnersh holiday rentals we have selected for you start as low as AU$92 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winnersh rentals

At Expedia, we put the best Winnersh holiday 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 Winnersh 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 Winnersh holiday.

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

Frequently asked questions

Can I find holiday rentals in Winnersh?

Yes, we give you a choice of holiday rentals where you'll be just 10 mi (16.1 km) from LEGOLAND® Windsor, giving you a secluded option if you want a quiet place to stay. Visitors like the top-notch restaurants and spas in Winnersh. While you're here, grab a bite or have a drink at the bars.

What are some of the best holiday rentals that Winnersh has to offer?

Spacious 6 Bedroom House in Denton Way: This holiday home rental outside of Winnersh has Netflix and free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals will I find in Winnersh?

Expedia has 3 holiday rentals for your stay in Winnersh.

What’s there to see and do in Winnersh?

Enjoy the area's cultural attractions such as Museum Of Berkshire Aviation, or get outdoors into nature at a spot like Thames Path. Nirvana Spa and LEGOLAND® Windsor are a couple of places you'll find in the wider area.

What’s a holiday rental in Winnersh like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winnersh. Holiday rentals feature extras such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a small group gathering.