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Holiday Rentals in Maidenhead

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Our top choices for Maidenhead holiday rentals

1. The Fox at Hurley - Delightful Property!

The Fox at Hurley - Delightful Property!
Maidenhead
The price is €172
includes taxes & fees
4 Oct - 5 Oct
The Fox at Hurley - Delightful Property!

2. Spacious, light apartment sleeps up to four

Spacious, light apartment sleeps up to four
Cookham
9.6 out of 10, Exceptional, (19 reviews)
"Beautifully refurbished property with very helpful hosts."
United Kingdom
Alexandra C.
The price is €253
includes taxes & fees
3 Oct - 4 Oct
Spacious, light apartment sleeps up to four

3. Lovely cottage in the heart of the picturesque village of Cookham

Lovely cottage in the heart of the picturesque village of Cookham
Cookham
10.0 out of 10, Exceptional, (1 review)
"Roseleigh Cottage is a lovely little house. It is ideally situated in central Cookham a stones throw from the Thames tow path and close to a range of pubs and other places to eat. The cottage is very well equipped and comfortable. We really enjoyed our stay as did our dog who appreciated the many walks thereabouts."
United States
Maggie L.
The price is €285
includes taxes & fees
9 Oct - 10 Oct
Lovely cottage in the heart of the picturesque village of Cookham

4. Shepherds Hut with Hot Tub Retreat - By Tempstay

Shepherds Hut with Hot Tub Retreat - By Tempstay
White Waltham
The price is €317
includes taxes & fees
4 Oct - 5 Oct
Shepherds Hut with Hot Tub Retreat - By Tempstay

5. Willow Court Farm

Willow Court Farm
4.0 star property
Windsor
10.0 out of 10, Exceptional, (215 reviews)
"Very nice, comfortable room, nice to have the kitchen. Lots of space outside to eat and relax! The kids loved the animals and that it’s clise to Legoland! The restaurant near by was really nice too and also easy to get around without a car."
Canada
Anne
The price is €176
includes taxes & fees
4 Oct - 5 Oct
Willow Court Farm

6. Copper Castle & Petting Farm near Legoland

Copper Castle & Petting Farm near Legoland
4.0 star property
Windsor
10.0 out of 10, Exceptional, (4 reviews)
"Fantastic accommodation and setting. We loved our stay in the copper castle. The hosts have thought of everything to make your stay as enjoyable as possible and the goats outside the accommodation are very friendly!"
United Kingdom
HAYLEY
The price is €199
includes taxes & fees
6 Oct - 7 Oct
Copper Castle & Petting Farm near Legoland

7. Beautiful 1-bed Studio in Bourne end

Beautiful 1-bed Studio in Bourne end
3.0 star property
Bourne End
10.0 out of 10, Exceptional, (2 reviews)
"Super stay, gorgeous studio with separate kitchen and bathroom, immaculate throughout. Very convenient for the train station and a beautiful walk by the Thames is just a few minutes away! "
United Kingdom
natalie
The price is €137
includes taxes & fees
11 Oct - 12 Oct
Beautiful 1-bed Studio in Bourne end

8. High Wycombe Apartments

High Wycombe Apartments
2.0 star property
High Wycombe
The price is €125
includes taxes & fees
4 Oct - 5 Oct
High Wycombe Apartments

9. Cavendish House

Cavendish House
5.0 star property
Windsor City Centre
9.8 out of 10, Exceptional, (80 reviews)
"Great place"
United Kingdom
Eva
The price is €259
includes taxes & fees
16 Oct - 17 Oct
Cavendish House

10. A Private Warm Welcoming Cosy Bungalow, 10 mins to Windsor or Beaconsfield Town.

A Private Warm Welcoming Cosy Bungalow, 10 mins to Windsor or Beaconsfield Town.
Farnham Royal
9.6 out of 10, Exceptional, (10 reviews)
"Thanks Joti for a pleasant stay. Property was clean and Host was very accommodating showing us round. Use of the BBQ was a great plus!"
United Kingdom
M. I.
The price is €417
includes taxes & fees
4 Oct - 5 Oct
A Private Warm Welcoming Cosy Bungalow, 10 mins to Windsor or Beaconsfield Town.

11. Hampden Apartments - The George

Hampden Apartments - The George
4.0 star property
Windsor City Centre
9.2 out of 10, Wonderful, (37 reviews)
"Amazing location, walking distance to shops, restaurants, the theatre and of course the castle. The apartment was clean on arrival and had everything we needed for our stay. "
United Kingdom
Alison
The price is €237
includes taxes & fees
21 Oct - 22 Oct
Hampden Apartments - The George

12. Stunning Central Windsor Town House

Stunning Central Windsor Town House
3.0 star property
Windsor City Centre
9.6 out of 10, Exceptional, (4 reviews)
"The house was perfect! The standard of the accommodation was excellent and it was located close to restaurants and all local attractions."
United Kingdom
Lisa
The price is €463
includes taxes & fees
8 Oct - 9 Oct
Stunning Central Windsor Town House

13. Elegant Windsor Flat -Short Walk to Windsor Castle, River Thames &Train Station

Elegant Windsor Flat -Short Walk to Windsor Castle, River Thames &Train Station
Eton
10.0 out of 10, Exceptional, (3 reviews)
"Gorgeous flat in a perfect location. There were so great places to walk to, including Windsor Castle. Highly recommend this place!"
United States
jennifer j.
The price is €197
includes taxes & fees
15 Oct - 16 Oct
Elegant Windsor Flat -Short Walk to Windsor Castle, River Thames &Train Station

14. HQ Aparthotel Farnborough

HQ Aparthotel Farnborough
4.0 star property
Rushmoor District
9.2 out of 10, Wonderful, (478 reviews)
"I always stay here when visiting family nearby as I live in USA."
United States
John
The price is €70
includes taxes & fees
11 Oct - 12 Oct
HQ Aparthotel Farnborough

15. Hampden Apartments - The Henry

Hampden Apartments - The Henry
4.0 star property
Windsor City Centre
9.0 out of 10, Wonderful, (23 reviews)
"Loved our stay great location. Apartment was clean and prepared for our visit. The property could use a few repairs but altogether it was a great place to stay. "
United States
Jeremy
The price is €250
includes taxes & fees
22 Oct - 23 Oct
Hampden Apartments - The Henry

16. Cozy Bracknell Apartment With Modern Amenities

Cozy Bracknell Apartment With Modern Amenities
3.0 star property
Bracknell
9.6 out of 10, Exceptional, (5 reviews)
"Great location and really clean apartment "
United Kingdom
Guy
The price is €147
includes taxes & fees
18 Oct - 19 Oct
Cozy Bracknell Apartment With Modern Amenities

17. IBEX HOUSE

IBEX HOUSE
3.0 star property
Reading
The price is €276
includes taxes & fees
3 Oct - 4 Oct
IBEX HOUSE

18. Salt House with parking

Salt House with parking
Henley-On-Thames
10.0 out of 10, Exceptional, (2 reviews)
"Nice property, a short walk from the town centre. Would start again when next in Henley"
United Kingdom
Lee
The price is €258
includes taxes & fees
12 Oct - 13 Oct
Salt House with parking

19. Livin’ Serviced Apartments

Livin’ Serviced Apartments
4.0 star property
Watford
9.0 out of 10, Wonderful, (355 reviews)
"Massive room with all amenities"
United Kingdom
Beatrice
The price is €92
includes taxes & fees
4 Oct - 5 Oct
Livin’ Serviced Apartments

20. Fabulous Central Windsor Town House

Fabulous Central Windsor Town House
3.0 star property
Windsor City Centre
10.0 out of 10, Exceptional, (1 review)
"House is exactly as in the pictures. Lovely, spacious and clean. Kids loved the bunk bed. "
United Kingdom
Abdullah
The price is €407
includes taxes & fees
4 Oct - 5 Oct
Fabulous Central Windsor Town House
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 Maidenhead Hotel Reviews

Find out more about Maidenhead

Everything you need to know about Maidenhead 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 Maidenhead holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Maidenhead holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Maidenhead holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Maidenhead. 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Maidenhead 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 Maidenhead holiday rentals we have selected for you start as low as €69 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Maidenhead rentals

At Expedia, we put the best Maidenhead 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 Maidenhead 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 Maidenhead 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 Maidenhead. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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Frequently asked questions

Can I find holiday rentals in Maidenhead?

Yes, there are holiday rentals in Maidenhead close to Braywick Leisure Centre, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Maidenhead speak positively about the scenic riverfront and lively bars in this destination. While you're in the area, you can also enjoy the top-notch restaurants and spas.

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

3 Bed House Sleeps 5 - Parking, Garden, Pets: This holiday home rental outside of Maidenhead offers a garden and free WiFi to help you feel comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Our travellers also rate 4 Bed Windsor Countryside Escape - By Tempstay as a favourite home for rent in Maidenhead.

How many holiday rentals are there in Maidenhead?

Choose from 32 Expedia holiday rentals in Maidenhead for a memorable holiday.

What’s there to see and do in Maidenhead?

Chiltern Hills and Thames Path are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Bray Marina and Cliveden House.

What’s a holiday rental in Maidenhead like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Maidenhead. Holiday rentals feature extras such as WiFi and washers and dryers so you'll feel right at home. If you're concerned about cleanliness, a holiday rental can provide a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a family trip.