Windsor and Maidenhead Holiday Rentals from NZ$319: Search Short-Term Rentals

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Our top choices for Windsor and Maidenhead holiday rentals

A modern building with dark siding, a glass door entrance, and two potted plants.

1. Willow Court Farm

Windsor

Anne

includes taxes & fees

9 Nov - 10 Nov

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

2. The Fox at Hurley - Delightful Property!

Maidenhead

A cozy living room with a green sofa, a decorative tapestry, and a high ceiling with exposed beams.

3. Copper Castle & Petting Farm near Legoland

Windsor

HAYLEY

includes taxes & fees

9 Nov - 10 Nov

A bedroom with a bed, a dresser, a window, and a chandelier.

4. Spacious, light apartment sleeps up to four

Cookham

Alexandra C.

includes taxes & fees

9 Nov - 10 Nov

A spacious living room with a dark sofa, a wooden coffee table, and a patterned rug.

5. Luxury 2 Bedroom Apartment

Clewer North

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with a central island, two bar stools, a stainless steel range hood, and a window with blinds.

6. Hampden Apartments - The William

Eton

Tony

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with a wooden countertop, a grey sofa, and a blue accent wall.

7. Windsor Home with Free Parking

Clewer South

Ian G.

includes taxes & fees

9 Nov - 10 Nov

A bedroom with a window, a bed with pillows, and a lamp.

8. Ascot Racecourse Apartment

Ascot

includes taxes & fees

9 Nov - 10 Nov

A narrow wooden pathway leading to a building with a checkered floor.

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

Cookham

Maggie L.

includes taxes & fees

9 Nov - 10 Nov

A modern house with a patio, a garden with various plants, and a wooden deck.

10. Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire

Wraysbury

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with dark cabinets, a wooden ceiling, and a large stove.

11. Cosy Cabin Close to Heathrow Airport, Windsor Castle, Legoland, Thorpe Park

Horton

Bruce S.

includes taxes & fees

7 Dec - 8 Dec

A modern kitchen with a blue accent wall, wooden staircase, and a dining area with a table set for four.

12. Heartwarming Windsor Cottage with Free Parking

Clewer East

Anonymous traveller

includes taxes & fees

9 Nov - 10 Nov

A historic building with a central courtyard, a fountain, and a clock tower.

13. Character Victorian apartment close to Windsor town with secure parking

Clewer East

Isabel

includes taxes & fees

9 Nov - 10 Nov

A dining area with a wooden table, chairs, a bowl of apples, a vase with flowers, a coat rack, and a spiral staircase.

14. Stylish terrace house in central Windsor, 5 mins walk to Windsor Castle and Eton

Windsor City Centre

includes taxes & fees

16 Nov - 17 Nov

A cozy interior with striped sofas, a kitchen area, and a bed with a view.

15. Shepherds Hut with Hot Tub Retreat - By Tempstay

White Waltham

includes taxes & fees

9 Nov - 10 Nov

A modern living room with a grey sofa, a dining table with chairs, and a large window with shelves.

16. Your Windsor Retreat | 1Bed/1Bath + Free Parking

Windsor City Centre

Toni

includes taxes & fees

9 Nov - 10 Nov

17. Relaxing guest house with Jacuzzi & boat hire

Wraysbury

Chaim

includes taxes & fees

9 Nov - 10 Nov

18. Studio Apartment | Walk to Shops & Castle

Windsor City Centre

Paula B.

A modern living room with a sofa and armchair, a coffee table, and a kitchen area with cabinets and appliances.

19. Windsor Gem: 1 Bed|1 Bath| Free Parking

Windsor City Centre

Michelle P.

includes taxes & fees

22 Nov - 23 Nov

A bedroom with a bed, bedside table, lamp, and a towel rack.

20. Spacious Apartment with Private Garden By Tempstay

Windsor City Centre

Sherry N.

includes taxes & fees

9 Nov - 10 Nov

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Top Windsor and Maidenhead Hotel Reviews

Willow Court Farm

Windsor

10/10 Excellent

We only stayed here for one night but loved it! Timely communication, good directions and the welcome was very friendly. The kids (and adults) loved all the animals and being able to visit them when they liked. The welcome box of groceries was awesome and very well used. The cabin is quite new so the fit-out is fresh (the bathroom could use a mirror beside the basin). Top marks for providing the kids bunk, which they loved, but must be a nightmare to make up! Extensive range of...

Karen

A cozy bedroom with a bed, bedside tables, a clock, and a window with curtains.

Park Farm Bed and Breakfast

Park

10/10 Excellent

Tara

A bedroom with a patterned wallpaper, a striped headboard, a bed with multiple pillows, a chair, and two bedside tables with lamps.

Bel & The Dragon Cookham

Maidenhead

10/10 Excellent

What a great place full of character, after staying at the Marriott this was a breath of fresh air, parking was the only problem. Is a very old pub so parts are very quirky. Bags have to be carried upstairs but was helped by staff on our arrival. Breakfast scrumptious. Didn’t eat at night as caught up with relatives. Peaceful walk along the river starts just down the road. Could definitely recommend, if I came back to this area would stay here again

Trina

An outdoor seating area with tables and chairs by a river, a bridge, and buildings in the background.

Sir Christopher Wren Hotel

Windsor City Centre

10/10 Excellent

Kathryn

A hotel room with a large bed, a seating area with a table, and a view of the city through large windows.

Goswell House

Windsor City Centre

10/10 Excellent

Joanne

An outdoor dining area with round tables and chairs, surrounded by glass walls and a clear sky.

Holiday Inn Express Windsor by IHG

Windsor City Centre

10/10 Excellent

Nikki

A hotel room with a view of a historic castle.

Macdonald Windsor Hotel

Windsor City Centre

10/10 Excellent

Mark Jason David

An outdoor seating area with tables and chairs under string lights, a large tree, and a building with a sign in the background.

The Royal Adelaide Hotel

Windsor City Centre

10/10 Excellent

Jayne

A buffet with various desserts and food items.

CIM Business Centre

Maidenhead

10/10 Excellent

We were looking for an overnight stay near London outside the M25 to make an easy start driving to Wales. This was excellent value with a good large breakfast included. Interesting old buildings, friendly staff, easy parking. Right on the edge of Cookham which is a beautiful village on the Thames. Plenty of places to eat even on a Sunday evening. I can definitely recommend this rather than the better known towns which are too busy and expensive.

Michael

Find out more about Windsor and Maidenhead

Everything you need to know about Windsor and 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 Windsor and 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 Windsor and Maidenhead holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor and Maidenhead holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor and 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 Windsor and 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 Windsor and Maidenhead holiday rentals we have selected for you start as low as NZ$319 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor and Maidenhead rentals

At Expedia, we put the best Windsor and 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 Windsor and 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 Windsor and 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 Windsor and 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.

Windsor and Maidenhead Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor and Maidenhead holiday rentals

1. Willow Court Farm

2. The Fox at Hurley - Delightful Property!

3. Copper Castle & Petting Farm near Legoland

4. Spacious, light apartment sleeps up to four

5. Luxury 2 Bedroom Apartment

6. Hampden Apartments - The William

7. Windsor Home with Free Parking

8. Ascot Racecourse Apartment

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

10. Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire

11. Cosy Cabin Close to Heathrow Airport, Windsor Castle, Legoland, Thorpe Park

12. Heartwarming Windsor Cottage with Free Parking

13. Character Victorian apartment close to Windsor town with secure parking

14. Stylish terrace house in central Windsor, 5 mins walk to Windsor Castle and Eton

15. Shepherds Hut with Hot Tub Retreat - By Tempstay

16. Your Windsor Retreat | 1Bed/1Bath + Free Parking

17. Relaxing guest house with Jacuzzi & boat hire

18. Studio Apartment | Walk to Shops & Castle

19. Windsor Gem: 1 Bed|1 Bath| Free Parking

20. Spacious Apartment with Private Garden By Tempstay

Find holiday rentals that suit your style

Top Windsor and Maidenhead Hotel Reviews

Willow Court Farm

10/10 Excellent

Find out more about Windsor and Maidenhead

Windsor and Maidenhead holiday rentals: An excellent choice for every season

How to find incredible deals on Windsor and Maidenhead rentals