Vacation Rentals in Windsor and Maidenhead

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Top Vacation Rentals in Windsor and Maidenhead

Willow Court Farm

4.0 star property
Windsor
10.0 out of 10, Exceptional, (198)
"Wonderful place ideal for families "
United Kingdom
Zoe
$142 nightly
The price is $171
Nov 13 - Nov 14
Total with taxes and fees
Willow Court Farm

Hampden Apartments - The Louis

3.0 star property
Eton
9.8 out of 10, Exceptional, (11)
"Love the location and loved the flat. All was perfect for us. "
United States
Shannon
Hampden Apartments - The Louis

Hampden Apartments - The George

4.0 star property
Windsor City Centre
9.0 out of 10, Wonderful, (34)
"Great location near shops, restaurants and train station. Second bedroom has bunk beds which would not be suitable for everyone. "
Canada
Margret
$281 nightly
The price is $281
Nov 14 - Nov 15
Total with taxes and fees
Hampden Apartments - The George

Riverside Boat Retreat on the River Thames

3.0 star property
Clewer East
$109 nightly
The price is $130
Nov 16 - Nov 17
Total with taxes and fees
Riverside Boat Retreat on the River Thames

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

Old Windsor
9.4 out of 10, Exceptional, (3)
"We were not sure how it would work out staying in someone's back garden, but it proved to be absolutely ideal for our family of five and was a cost-effective way of staying near London. The cabin is thoughtfully kitted out and was spotlessly clean. The owners are lovely and even let our children see their rabbits. It was easy to get into London for day trips with street parking available near Egham Station. It was very handy for Legoland. We were worried how hot the cabin would get in the...
United Kingdom
David S.
$169 nightly
The price is $169
Nov 16 - Nov 17
Total with taxes and fees
A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.

Character Victorian apartment close to Windsor town with secure parking

Clewer East
10.0 out of 10, Exceptional, (1)
"A gorgeous opulent place to stay while in Windsor. We appreciated the extra touches like the fresh milk for tea!"
Canada
Isabel
$280 nightly
The price is $280
Nov 16 - Nov 17
Total with taxes and fees
Character Victorian apartment close to Windsor town with secure parking

haven Valley near the theme park

Old Windsor
10.0 out of 10, Exceptional, (1)
"Me and my family stayed here as we had a wedding nearby. The place accommodated all of us. Very spacious and clean. Host is amazing! "
United Kingdom
Akarshana S.
$343 nightly
The price is $391
Dec 2 - Dec 3
Total with taxes and fees
haven Valley near the theme park

Spacious, light apartment sleeps up to four

Cookham
9.8 out of 10, Exceptional, (18)
"Overnight Stay convenient for Cookham and Bourne End. Breakfast is a nice touch."
United States
Peter r.
$275 nightly
The price is $275
Nov 13 - Nov 14
Total with taxes and fees
Spacious, light apartment sleeps up to four

Windsor Home with Free Parking

Clewer South
$224 nightly
The price is $224
Nov 19 - Nov 20
Total with taxes and fees
Windsor Home with Free Parking

Crazy Fox Garden Cabin - From 120 Per Night

2.0 star property
Maidenhead
Crazy Fox Garden Cabin - From 120 Per Night

Stylish Lodge At Windsor Racecourse Marina

Clewer North
10.0 out of 10, Exceptional, (4)
"We had an excellent stay and thoroughly enjoyed your lovely home. Thank you for the hospitality and quick responses with our questions. Would definitely stay here again!"
United States
Kristine M.
$468 nightly
The price is $473
Nov 24 - Nov 25
Total with taxes and fees
Stylish Lodge At Windsor Racecourse Marina

MayGrove Retreat - Sleeps 2 - Jacuzzi & boat hire

Wraysbury
10.0 out of 10, Exceptional, (17)
"Comfortable, clean, and great location. Hosts very attentive and helpful. Thoroughly recommend this holiday let. Colin."
United Kingdom
Colin C.
$334 nightly
The price is $334
Nov 21 - Nov 22
Total with taxes and fees
MayGrove Retreat - Sleeps 2 - Jacuzzi & boat hire

Inviting 2-bed Cottage in Windsor

3.0 star property
Windsor City Centre
2.0 out of 10, (1)
"We had absolutely no heating. I tried several times to contact the owner by email, messenger and by phoning her. No reply. I had been in contact with her regarding check in via email and messenger, I even sent a photo of the temperature in the house. 10 degrees. I had to source 2 radiators myself, which a kind neighbour lent us. I would like a refund for our inconvenience "
United Kingdom
Anonymous traveler
$239 nightly
The price is $239
Dec 1 - Dec 2
Total with taxes and fees
Inviting 2-bed Cottage in Windsor

Stay in Style Opposite Windsor Castle| Parking

Windsor City Centre
8.6 out of 10, Excellent, (8)
"On arrival I thought we had the wrong apartment block. The entrance is not on the road communicated, but on a private road running parallel to the Palace buildings. The actual entrance was dirty and just horrible, there is a restaurant in the building next door and its extractor vent is next to the entrance - clearly fish and chips are a big seller because the smell is overpowering. The entrance was filled with leave debris and just not very welcoming. Once inside the hallway was not inviting at...
United Kingdom
Samantha B.
$339 nightly
The price is $343
Dec 4 - Dec 5
Total with taxes and fees
Stay in Style Opposite Windsor Castle| Parking

Stay In Style With Castle Views/Prime Spot Windsor

Windsor City Centre
10.0 out of 10, Exceptional, (2)
"This place was perfect for us. It’s exactly as listed on the site, super cute and very comfortable plus there really is a view of the castle! We had a couple small things we needed help with and the host management company was very helpful and responsive. There’s a cut through to the long walk just up the street and you can be in the center of town in 10 min or less. Would stay again!"
United States
Amy R.
$201 nightly
The price is $203
Nov 16 - Nov 17
Total with taxes and fees
Stay In Style With Castle Views/Prime Spot Windsor

Spotless & Stylish Stay in Windsor – Free Parking & Ultra Fast Internet

2.0 star property
Park
$79 nightly
The price is $79
Nov 13 - Nov 14
Total with taxes and fees
Spotless & Stylish Stay in Windsor – Free Parking & Ultra Fast Internet

Doorstep Of Windsor Castle Chic: 1BR|Parking

Windsor City Centre
8.8 out of 10, Excellent, (3)
"Lovely stay in Windsor, great apartment, clean with all facilities needed. Location is superb"
United Kingdom
sue a.
$213 nightly
The price is $215
Nov 13 - Nov 14
Total with taxes and fees
Doorstep Of Windsor Castle Chic: 1BR|Parking

Charming Studio with Stunning Windsor Castle Views

Windsor City Centre
10.0 out of 10, Exceptional, (1)
Charming Studio with Stunning Windsor Castle Views

Thames Retreat

3.0 star property
Wraysbury
$450 nightly
The price is $541
Nov 16 - Nov 17
Total with taxes and fees
Thames Retreat
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 Windsor and Maidenhead Hotel Reviews

Find out more about Windsor and Maidenhead

Discover your perfect Windsor and Maidenhead vacation rental with Expedia

How many vacation rentals are available in Windsor and Maidenhead?


Expedia has plenty of vacation rentals to choose from in and around  Windsor and Maidenhead, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Windsor and Maidenhead?


The selection of Windsor and Maidenhead vacation rentals we have selected for you start as low as $78 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Windsor and Maidenhead?


Vacation rentals in Windsor and Maidenhead come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Windsor and Maidenhead vacation rentals to suit everyone. 


Why should I choose a vacation rental in Windsor and Maidenhead?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Windsor and Maidenhead vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Windsor and Maidenhead?


Find vacation rentals in Windsor and Maidenhead by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Windsor and Maidenhead.  


What amenities are available in a vacation rental in Windsor and Maidenhead?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Windsor and Maidenhead vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Windsor and Maidenhead?   


Everytime is a great time to head to Windsor and Maidenhead! Staying in a Windsor and Maidenhead vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Windsor and Maidenhead. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Windsor and Maidenhead vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Windsor and Maidenhead, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Windsor and Maidenhead vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.