A calm river with buildings and a bridge reflecting on the water.

Maidenhead Vacation Rentals

Q: What are some of the best vacation rentals in Maidenhead?

3 Bed House Sleeps 5 - Parking, Garden, Pets : Located near Maidenhead, this vacation home rental 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 you can cook with friends or family. Our travelers also rate 4 Bed Windsor Countryside Escape - By Tempstay as a favorite home for rent in Maidenhead.

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Dates

November 2026

December 2026

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Our top choices for Maidenhead vacation 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!

Maidenhead

￥31,302 total

includes taxes & fees

Nov 8 - Nov 9

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

2. Spacious, light apartment sleeps up to four

Cookham

Alexandra C.

￥40,671 total

includes taxes & fees

Nov 9 - Nov 10

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

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

Cookham

Maggie L.

￥45,888 total

includes taxes & fees

Nov 10 - Nov 11

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

4. Shepherds Hut with Hot Tub Retreat - By Tempstay

White Waltham

￥57,787 total

includes taxes & fees

Nov 8 - Nov 9

A modern house with a dark exterior, a patio with outdoor furniture, and a white umbrella.

5. Willow Court Farm

Windsor

Anne

￥33,857 total

includes taxes & fees

Nov 6 - Nov 7

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

Windsor

Susan

￥41,527 total

includes taxes & fees

Nov 7 - Nov 8

A bedroom with a bed, a door leading to a balcony, and a view of a garden.

7. Beautiful 1-bed Studio in Bourne end

Bourne End

natalie

￥24,697 total

includes taxes & fees

Nov 9 - Nov 10

An outdoor kitchen with a grill, a sink, and a dining area with a table and chairs.

8. A Warm Welcoming Cosy Bungalow, 10 mins to Windsor

Farnham Royal

M. I.

￥70,482 total

includes taxes & fees

Nov 8 - Nov 9

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

9. Hampden Apartments - The William

Eton

Tony

￥26,869 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with a built-in washing machine, a microwave, and a stove.

10. High Wycombe Apartments

High Wycombe

￥22,557 total

includes taxes & fees

Nov 9 - Nov 10

A modern hotel room with a wooden floor, a bed with a grey blanket, a bedside table, and a desk with a laptop.

11. HQ Aparthotel Farnborough

Rushmoor District

John

￥14,213 total

includes taxes & fees

Nov 8 - Nov 9

A modern kitchen with a checkered floor, wooden and green bowls, and hanging pendant lights.

12. Livin’ Serviced Apartments

Watford

Kathryn

￥15,506 total

includes taxes & fees

Nov 8 - Nov 9

A cobblestone street with buildings, a sign for 'The Castle Hotel,' and outdoor seating.

13. 1BR|Parking|Doorstep Of Windsor Castle|By Tempstay

Windsor City Centre

Richard J.

￥39,505 total

includes taxes & fees

Nov 30 - Dec 1

A modern hotel room with a large bed, a sofa, a TV, and a view of the city.

14. Ferrum

Tokyngton

"We loved Ferrum! It’s a close location to Wembley Stadium and near a ton of grocery stores and restaurants. We also traveled from the airport to the hotel and the train dropped us right across the street, which is a huge plus!! Everyone was so nice to us and the description on the listing when we booked matched exactly what was said. Didn’t even realize with the full kitchen we got everything we needed to cook, which is a huge plus if you want to stay in and cook a meal"

Mario Arturo

￥42,223 total

includes taxes & fees

Nov 8 - Nov 9

A bedroom with a large bed, two bedside tables, a tray with breakfast, and a view of the sea through the window.

15. Hampden Apartments - The Henry

Windsor City Centre

Dave

￥39,139 total

includes taxes & fees

Nov 15 - Nov 16

A modern dining area with a glass table, two black chairs, and a small bonsai tree.

16. IBEX HOUSE

Reading

￥49,965 total

includes taxes & fees

Nov 11 - Nov 12

17. Apartment Sleeps 5 With Parking Free

Feltham West

￥22,514 total

includes taxes & fees

Nov 30 - Dec 1

A modern bedroom with a large bed, a skylight, and a blue accent wall.

18. Heathrow Windsor Apart Hotel

Colnbrook

Jennifer

￥18,829 total

includes taxes & fees

Nov 8 - Nov 9

A bedroom with a large bed, a wooden door, a sliding glass door to a balcony, and a view of the outside.

19. Staines Riverside by Charles Hope

Staines

bhargav

￥23,629 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with a central island, recessed lighting, and a view to the outside.

20. Stunning Central Windsor Town House

Windsor City Centre

Lisa

￥87,678 total

includes taxes & fees

Nov 15 - Nov 16

View all properties

Find vacation rentals that suit your style

Top Maidenhead Hotel Reviews

A stone building with multiple windows and a brick chimney, surrounded by a well-maintained garden with various plants and a pathway.

Hurley House Hotel

Maidenhead

10/10 Excellent

luis

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

Harriett

A building with a reception area and a sign that reads "The Fix & Goose."

The Fox & Goose Hotel

Ealing

10/10 Excellent

Angela

An outdoor patio area with round tables and chairs, a fire feature, and a view of the interior through large glass doors.

Monkey Island Estate - Small Luxury Hotels of the World

Maidenhead

10/10 Excellent

Beautiful little hotel in the cute little town of Bray. It was a delight, though dining at hotel was limited. I don't know why someone would choose to stay at an airport hotel when there is a wonderful place like this just a short drive away. Very convenient to Heathrow. Very romantic hotel. On an actual island, it was very nice in fall but I imagine it would be spectacular in summer. Only downside is no pool. Total delight!

Alice

A hotel room with two beds, a desk with a lamp, a chair, and a painting on the wall.

Best Western Chiswick Rooms

Hammersmith

10/10 Excellent

Kellie

A hotel lobby with a wooden floor, a reception desk, and a dining area with chairs and tables.

Premier Inn Maidenhead Town Centre

Maidenhead

10/10 Excellent

John

A reception area with a herringbone wood floor, a reception desk, and a circular mirror on the wall.

Staybridge Suites London Heathrow - Bath Road by IHG

Heathrow Villages

10/10 Excellent

Kristal

A spacious indoor area with multiple seating arrangements, a large tree, and a unique sculpture.

Hilton London Heathrow Airport Hotel

Heathrow Villages

10/10 Excellent

Arthur

A large brick building with a symmetrical facade, a central entrance, and a well-maintained lawn with a curved driveway.

Four Seasons Hotel Hampshire

Hook

10/10 Excellent

Melanie

A historic hotel with a classic facade, multiple windows, and a balcony with decorative railings.

Castle Hotel Windsor

Windsor City Centre

10/10 Excellent

Melanie

Crowne Plaza London Heathrow T4 by IHG

Heathrow Villages

10/10 Excellent

Trent

An outdoor patio area with round tables and chairs, surrounded by lush greenery and a brick building in the background.

The Bull Hotel

Gerrards Cross

10/10 Excellent

Anonymous traveler

A modern hotel with a curved glass facade, a parking garage, and a well-maintained garden area.

Hilton Garden Inn London Heathrow Terminal 2 and 3

Heathrow Villages

10/10 Excellent

Matthew

A hotel lobby with reception desks, seating areas, and a high ceiling with a starry design.

Holiday Inn Express London Heathrow T4 by IHG

Heathrow Villages

10/10 Excellent

Billie

Find out more about Maidenhead

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Frequently Asked Questions

Can I find vacation rentals in Maidenhead?

Yes, there are vacation rentals in Maidenhead close to Braywick Leisure Centre, or you can choose a more remote option if you want 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 vacation rentals in Maidenhead?

3 Bed House Sleeps 5 - Parking, Garden, Pets: Located near Maidenhead, this vacation home rental 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 you can cook with friends or family. Our travelers also rate 4 Bed Windsor Countryside Escape - By Tempstay as a favorite home for rent in Maidenhead.

How many vacation rentals are there in Maidenhead?

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

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 vacation rental in Maidenhead like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Maidenhead. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from shared 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 hotel, which makes a vacation rental an attractive choice for a family getaway.

Maidenhead Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Maidenhead vacation rentals

1. The Fox at Hurley - Delightful Property!

2. Spacious, light apartment sleeps up to four

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

4. Shepherds Hut with Hot Tub Retreat - By Tempstay

5. Willow Court Farm

6. Copper Castle & Petting Farm near Legoland

7. Beautiful 1-bed Studio in Bourne end

8. A Warm Welcoming Cosy Bungalow, 10 mins to Windsor

9. Hampden Apartments - The William

10. High Wycombe Apartments

11. HQ Aparthotel Farnborough

12. Livin’ Serviced Apartments

13. 1BR|Parking|Doorstep Of Windsor Castle|By Tempstay

14. Ferrum

15. Hampden Apartments - The Henry

16. IBEX HOUSE

17. Apartment Sleeps 5 With Parking Free

18. Heathrow Windsor Apart Hotel

19. Staines Riverside by Charles Hope

20. Stunning Central Windsor Town House

Find vacation rentals that suit your style

Top Maidenhead Hotel Reviews

Hurley House Hotel

10/10 Excellent

Find out more about Maidenhead

Frequently Asked Questions

Can I find vacation rentals in Maidenhead?

What are some of the best vacation rentals in Maidenhead?

How many vacation rentals are there in Maidenhead?

What’s there to see and do in Maidenhead?

What’s a vacation rental in Maidenhead like?