An aerial view of a town with a river, green spaces, and historic buildings.

Maidenhead Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Maidenhead holiday rentals

A neatly made bed with two pillows, a bedside table with a lamp, and a bedside table with a decorative item.

1. The Fox at Hurley - Delightful Property!

The Fox at Hurley - Delightful Property!
Maidenhead
The price is NZ$344
includes taxes & fees
4 Oct - 5 Oct
The Fox at Hurley - Delightful Property!
A bedroom with a bed, a dresser, a window, and a chandelier.

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 NZ$487
includes taxes & fees
29 Sept - 30 Sept
Spacious, light apartment sleeps up to four
A narrow wooden pathway leading to a building with a checkered floor.

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 NZ$539
includes taxes & fees
29 Sept - 30 Sept
Lovely cottage in the heart of the picturesque village of Cookham
A cozy interior with striped sofas, a kitchen area, and a bed with a view.

4. Shepherds Hut with Hot Tub Retreat - By Tempstay

Shepherds Hut with Hot Tub Retreat - By Tempstay
White Waltham
The price is NZ$633
includes taxes & fees
29 Sept - 30 Sept
Shepherds Hut with Hot Tub Retreat - By Tempstay
A modern house with a dark exterior, a patio with outdoor furniture, and a white umbrella.

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 NZ$351
includes taxes & fees
30 Sept - 1 Oct
Willow Court Farm
A cozy living room with a green sofa, a decorative tapestry, and a high ceiling with exposed beams.

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 NZ$374
includes taxes & fees
29 Sept - 30 Sept
Copper Castle & Petting Farm near Legoland
A bedroom with a bed, a wooden shelf with a small plant, and a wall-mounted plant.

7. Cosy Studio Near Heathrow Airport/ Free Parking

Cosy Studio Near Heathrow Airport/ Free Parking
3.0 star property
Staines
Cosy Studio Near Heathrow Airport/ Free Parking
A compact kitchen with modern appliances, a dining area with chairs, and a door.

8. High Wycombe Apartments

High Wycombe Apartments
2.0 star property
High Wycombe
The price is NZ$245
includes taxes & fees
29 Oct - 30 Oct
High Wycombe Apartments
A hallway with a wooden floor, a white wall with a textured artwork, and a wooden door.

9. IBEX HOUSE

IBEX HOUSE
3.0 star property
Reading
The price is NZ$539
includes taxes & fees
30 Sept - 1 Oct
IBEX HOUSE
A modern hotel room with a wooden floor, a bed with a grey blanket, a bedside table, and a desk with a laptop.

10. 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 NZ$140
includes taxes & fees
25 Oct - 26 Oct
HQ Aparthotel Farnborough
A modern bedroom with a large bed, a skylight, and a blue accent wall.

11. Heathrow Windsor Apart Hotel

Heathrow Windsor Apart Hotel
2.0 star property
Colnbrook
6.8 out of 10, (9 reviews)
"Beautiful place!"
United States
Jennifer
The price is NZ$261
includes taxes & fees
3 Oct - 4 Oct
Heathrow Windsor Apart Hotel
A house with a patio, a barbecue grill, and a dining area with outdoor furniture.

12. Brook House

Brook House
3.0 star property
Stoke Poges
The price is NZ$3,548
includes taxes & fees
29 Sept - 30 Sept
Brook House
A modern living room with a flat-screen TV mounted on a wooden wall, a window with curtains, a wooden bench, and a framed picture on the wall.

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 NZ$381
includes taxes & fees
14 Oct - 15 Oct
Elegant Windsor Flat -Short Walk to Windsor Castle, River Thames &Train Station
A modern living room with a flat-screen TV, a sofa, and a coffee table. There is a kitchen area with a dining table and bar stools.

14. 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 NZ$469
includes taxes & fees
21 Oct - 22 Oct
Hampden Apartments - The George
A modern kitchen with a dining area, a water dispenser, and a view of the backyard.

15. Salt House with parking

Salt House with parking
Henley-On-Thames
10.0 out of 10, Exceptional, (1 review)
"Perfect in every way! The house was spotless and had everything we needed. It's situated approx 7 mins away from town in one direction, so you can leave the car on the drive, (a major plus) and 10 mins walk away from the woods in the other: ideal for an early morning, or any time dog walk! There's a hose in the garden for dirty boots and dogs and the back gate locks for security. Heating was easy to adjust and the fire worked beautifully. The TV was easy to operate and the Wifi was fab!...
United Kingdom
Lisa
The price is NZ$503
includes taxes & fees
30 Sept - 1 Oct
Salt House with parking
An outdoor kitchen with a grill, a sink, and a dining area with a table and chairs.

16. 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 NZ$814
includes taxes & fees
30 Sept - 1 Oct
A Private Warm Welcoming Cosy Bungalow, 10 mins to Windsor or Beaconsfield Town.
A bedroom with a bed, a door leading to a balcony, and a view of a garden.

17. 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 NZ$244
includes taxes & fees
12 Oct - 13 Oct
Beautiful 1-bed Studio in Bourne end
A modern kitchen with white cabinets, a stainless steel sink, and a built-in oven.

18. Buckingham Apartments

Buckingham Apartments
3.0 star property
High Wycombe
7.2 out of 10, Good, (19 reviews)
"This hotel is not as advertised or as described - be warned "
United Kingdom
Alexandra
The price is NZ$238
includes taxes & fees
29 Sept - 30 Sept
Buckingham Apartments
A modern living room with a sofa, coffee table, and dining area.

19. Modern apartment in the vicinity of Heathrow/Windsor/Slough

Modern apartment in the vicinity of Heathrow/Windsor/Slough
Colnbrook
10.0 out of 10, Exceptional, (3 reviews)
"Very attractive apartment- new furnishings and appliances and state of the art bathrooms.Host was very helpful in meeting our requests and excellent communication.Also, wonderful location close to Heathrow and Windsor Castle."
United States
Laurie R.
The price is NZ$468
includes taxes & fees
29 Sept - 30 Sept
Modern apartment in the vicinity of Heathrow/Windsor/Slough
A modern kitchen with a central island, pendant lighting, and a dining area with a glass table.

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 NZ$875
includes taxes & fees
13 Oct - 14 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Maidenhead Hotel Reviews

Sofitel London Heathrow

Sofitel London Heathrow

8/10 Good
"Room need to be update. Lacks the modern amenities."
David 1-night trip
Posted less than an hour ago
Sofitel London Heathrow

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, 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 NZ$119 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. 

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 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 28 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.