Photo by don cload

Winnersh Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winnersh vacation rentals

Groomes Country House

Groomes Country House
3.5 star property
Bordon
$3,398 nightly
The price is $4,077
Dec 29 - Dec 30
Total with taxes and fees
Groomes Country House

2 Bed - Sleeps 6 - Free Parking

2 Bed - Sleeps 6 - Free Parking
3.5 star property
Bracknell
10.0 out of 10, Exceptional, (1)
"Lovely apartment and had everything we needed. Good communication from the host. "
United Kingdom
Helen
$163 nightly
The price is $195
Jan 8 - Jan 9, 2026
Total with taxes and fees
2 Bed - Sleeps 6 - Free Parking

Willow Court Farm

Willow Court Farm
4.0 star property
Windsor
10.0 out of 10, Exceptional, (199)
"Wonderful place ideal for families "
United Kingdom
Zoe
$138 nightly
The price is $166
Jan 15 - Jan 16, 2026
Total with taxes and fees
Willow Court Farm

HQ Aparthotel Farnborough

HQ Aparthotel Farnborough
4.0 star property
Rushmoor District
9.0 out of 10, Wonderful, (448)
"The room is tidy and customer services is good in the hotel"
United Kingdom
Lewis
$78 nightly
The price is $93
Jan 4 - Jan 5, 2026
Total with taxes and fees
HQ Aparthotel Farnborough

VICTORIA HOUSE by Aeria Apartments

VICTORIA HOUSE by Aeria Apartments
4.0 star property
Reading City Centre
7.8 out of 10, Good, (40)
"As always, we love Victoria while traveling to UK."
United States
Trailer
VICTORIA HOUSE by Aeria Apartments

Cosy 1 Bedroom Apartment Private Access in Guildford

Cosy 1 Bedroom Apartment Private Access in Guildford
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
$145 nightly
The price is $145
Jan 2 - Jan 3, 2026
Total with taxes and fees
Cosy 1 Bedroom Apartment Private Access in Guildford

Blue sky at Wallis square

Blue sky at Wallis square
4.0 star property
Rushmoor District
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

PREMIER SUITES Reading

PREMIER SUITES Reading
4.0 star property
Reading City Centre
8.8 out of 10, Excellent, (157)
"Our stay was amazing. We stayed to go to the reading festiabl and it was brilliantly located 10 min walk to the train station. And abouve a mall wirh so many shops and parking!! Will definitely be staying here again."
United Kingdom
Emma
$100 nightly
The price is $120
Dec 28 - Dec 29
Total with taxes and fees
PREMIER SUITES Reading

Spacious, light apartment sleeps up to four

Spacious, light apartment sleeps up to four
Cookham
9.8 out of 10, Exceptional, (18)
"Beautifully refurbished property with very helpful hosts."
United Kingdom
Alexandra C.
$284 nightly
The price is $284
Dec 26 - Dec 27
Total with taxes and fees
Spacious, light apartment sleeps up to four

A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.

A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.
Old Windsor
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.
$174 nightly
The price is $174
Jan 1 - Jan 2, 2026
Total with taxes and fees
A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.

Staines City Centre by Charles Hope

Staines City Centre by Charles Hope
3.5 star property
Staines Town Centre
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

Oaklawn Serviced Apartments

Oaklawn Serviced Apartments
3.5 star property
Woking
9.6 out of 10, Exceptional, (10)
"Host is amazing ! "
United States
Erin
$201 nightly
The price is $201
Jan 8 - Jan 9, 2026
Total with taxes and fees
Oaklawn Serviced Apartments

Ivory Lodge

Ivory Lodge
4.0 star property
Reading
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
$240 nightly
The price is $240
Jan 5 - Jan 6, 2026
Total with taxes and fees
Ivory Lodge

Charming Cottage within Ancient Woodland Forest

Charming Cottage within Ancient Woodland Forest
Cobham
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.
$259 nightly
The price is $259
Jan 2 - Jan 3, 2026
Total with taxes and fees
Charming Cottage within Ancient Woodland Forest

Staines Riverside by Charles Hope

Staines Riverside by Charles Hope
4.0 star property
Staines
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

Central Spacious apartment located in the heart of it all!

Central Spacious apartment located in the heart of it all!
Reading
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.
$201 nightly
The price is $201
Jan 1 - Jan 2, 2026
Total with taxes and fees
Central Spacious apartment located in the heart of it all!

1400 Cottage An Enchanting Unique Stay - From 120 Per Night

1400 Cottage An Enchanting Unique Stay - From 120 Per Night
3.0 star property
Henley-on-Thames
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
$298 nightly
The price is $298
Jan 8 - Jan 9, 2026
Total with taxes and fees
1400 Cottage An Enchanting Unique Stay - From 120 Per Night

A new 3-bed flat with en-suite near Heathrow

A new 3-bed flat with en-suite near Heathrow
Ashford
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.
$325 nightly
The price is $325
Dec 27 - Dec 28
Total with taxes and fees
A new 3-bed flat with en-suite near Heathrow

Hampden Apartments - The Louis

Hampden Apartments - The Louis
3.0 star property
Eton
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

Kensington House by Solitaire Suites

Kensington House by Solitaire Suites
3.0 star property
Slough
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
$161 nightly
The price is $193
Jan 1 - Jan 2, 2026
Total with taxes and fees
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winnersh Hotel Reviews

Find out more about Winnersh

Everything you need to know about Winnersh 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 Winnersh 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 Winnersh vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winnersh vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winnersh 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 Winnersh rentals

At Expedia, we put the best Winnersh 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 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 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 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 vacation rentals in Winnersh?

Yes, we have vacation rentals where you'll be only 10 mi (16.1 km) from LEGOLAND® Windsor, offering you a more remote option if you'd like a quiet spot 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's the top vacation rental that Winnersh has to offer?

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

How many vacation rentals will I find in Winnersh?

Expedia has 3 vacation 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 larger area.

What’s a vacation rental in Winnersh like?

Vacation rentals are private properties you can stay in for a long or short time in Winnersh. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family getaway.