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

Maidenhead Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Maidenhead vacation homes

A modern kitchen with a central island, bar stools, and a large wall clock.

1. Rainfall Shower | Pool/Snooker | x 4 Cars

Rainfall Shower | Pool/Snooker | x 4 Cars
Altwood
8.0 out of 10, Very good, (4 reviews)
"A decent place. Had everything we needed and would happily recommend."
United Kingdom
Darren A.
Rainfall Shower | Pool/Snooker | x 4 Cars
A cozy interior with striped sofas, a kitchen area, and a bed with a view.

2. Shepherds Hut with Hot Tub Retreat - By Tempstay

Shepherds Hut with Hot Tub Retreat - By Tempstay
White Waltham
The price is CA $349
CA $511 total
includes taxes & fees
Oct 8 - Oct 9
Shepherds Hut with Hot Tub Retreat - By Tempstay
A modern living room with a sofa, armchair, and dining area.

3. Stunning Place near Windsor & Heathrow, 3BR House

Stunning Place near Windsor & Heathrow, 3BR House
Burnham
10.0 out of 10, Exceptional, (2 reviews)
"Sleeps 6 comfortably. Nice for a family!"
United States
Grady R.
The price is CA $305
CA $475 total
includes taxes & fees
Oct 10 - Oct 11
Stunning Place near Windsor & Heathrow, 3BR House
An outdoor kitchen with a grill, a sink, and a dining area with a table and chairs.

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

A Warm Welcoming Cosy Bungalow, 10 mins to Windsor
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 CA $453
CA $654 total
includes taxes & fees
Oct 7 - Oct 8
A Warm Welcoming Cosy Bungalow, 10 mins to Windsor
A dining area with a long table set for six, surrounded by wooden chairs, a sofa, and a small side table with a lamp.

5. 4BR Home Near Windsor Castle Legoland

4BR Home Near Windsor Castle Legoland
2.0 star property
Clewer North
The price is CA $1,211
CA $1,867 total
includes taxes & fees
Oct 26 - Oct 27
4BR Home Near Windsor Castle Legoland
A modern kitchen with a blue accent wall, wooden staircase, and a dining area with a table set for four.

6. Heartwarming Windsor Cottage with Free Parking

Heartwarming Windsor Cottage with Free Parking
Clewer East
10.0 out of 10, Exceptional, (1 review)
"Beautiful place to stay."
United States
Anonymous traveller
The price is CA $255
CA $415 total
includes taxes & fees
Oct 8 - Oct 9
Heartwarming Windsor Cottage with Free Parking
A cozy bedroom with a large bed, a grey sofa, a patterned rug, a window with curtains, and a fireplace.

7. Windsor Castle Amazing Cottage | 2-Min Walk | Central & Stylish

Windsor Castle Amazing Cottage | 2-Min Walk | Central & Stylish
Windsor City Centre
8.0 out of 10, Very good, (4 reviews)
"Great house. Perfect location. A wonderful stay."
United States
David T.
The price is CA $272
CA $437 total
includes taxes & fees
Oct 7 - Oct 8
Windsor Castle Amazing Cottage | 2-Min Walk | Central & Stylish
A modern living room with a white leather armchair, a fireplace with a vintage stove, and a wooden floor.

8. Mills Cottage - Sleeps 4

Mills Cottage - Sleeps 4
Henley-On-Thames
8.0 out of 10, Very good, (1 review)
"Nice location but the road is very busy "
United Kingdom
ricky j.
The price is CA $269
CA $448 total
includes taxes & fees
Nov 1 - Nov 2
Mills Cottage - Sleeps 4
A modern living room with a sofa and armchair, a coffee table, and a kitchen area with cabinets and appliances.

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

Windsor Gem: 1 Bed|1 Bath| Free Parking
Windsor City Centre
10.0 out of 10, Exceptional, (1 review)
"Great looking apartment. "
United States
Michelle P.
The price is CA $279
CA $373 total
includes taxes & fees
Oct 27 - Oct 28
Windsor Gem: 1 Bed|1 Bath| Free Parking
A room with two beds, a large screen displaying a streaming service interface, and a window with a view of the outside.

10. Windsor Luxe Living – 3BR Near Windsor Castle

Windsor Luxe Living – 3BR Near Windsor Castle
Clewer East
The price is CA $358
CA $358 total
includes taxes & fees
Nov 1 - Nov 2
Windsor Luxe Living – 3BR Near Windsor Castle
A room with a large mirror reflecting a living area, a kitchen with white cabinets, and a window with a view of greenery.

11. Badgemore Cottage - Pet friendly, sleeps 8

Badgemore Cottage - Pet friendly, sleeps 8
Henley-On-Thames
10.0 out of 10, Exceptional, (1 review)
"Fantastic rental property on the edge of Henley-on-Thames. The bungalow is secluded and comfortable, with a nice living area, spacious kitchen, and private garden. We spent almost a week here for a family getaway and were delighted with the property. The location is great for nearby attractions like Windsor and Legoland. The property manager was very helpful when we had questions."
United States
Andrew F.
The price is CA $422
CA $743 total
includes taxes & fees
Oct 8 - Oct 9
Badgemore Cottage - Pet friendly, sleeps 8
A modern kitchen with a dining area, a water dispenser, and a view of the backyard.

12. 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 CA $236
CA $415 total
includes taxes & fees
Oct 15 - Oct 16
Salt House with parking
A modern kitchen with a skylight, a dining area with wooden chairs, and a view of a backyard.

13. Apple Blossom - Central Henley with free road parking

Apple Blossom - Central Henley with free road parking
Henley-On-Thames
10.0 out of 10, Exceptional, (1 review)
"Very well presented house with everything you need for a great stay. Close to the town yet quiet. "
United Kingdom
Colin
The price is CA $274
CA $453 total
includes taxes & fees
Oct 8 - Oct 9
Apple Blossom - Central Henley with free road parking
A modern kitchen with a central island, recessed lighting, and a view to the outside.

14. 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 CA $325
CA $746 total
includes taxes & fees
Oct 8 - Oct 9
Stunning Central Windsor Town House
A modern kitchen with white cabinetry, a granite countertop, a built-in oven, and a window with a view of greenery.

15. Luxury 4BR Windsor Near M4 LHR Free Parking

Luxury 4BR Windsor Near M4 LHR Free Parking
2.0 star property
Clewer East
The price is CA $983
CA $1,581 total
includes taxes & fees
Oct 25 - Oct 26
Luxury 4BR Windsor Near M4 LHR Free Parking
A modern kitchen with built-in appliances, a dining area with a table and chairs, and a hallway leading to another room.

16. 3 Bed 3 Bath Home| Windsor| Parking - By Tempstay

3 Bed 3 Bath Home| Windsor| Parking - By Tempstay
Windsor City Centre
10.0 out of 10, Exceptional, (4 reviews)
"We all had a great time in Windsor at this lovely property. Great location, easy to find and park and walking distance to all the famous sites."
United Kingdom
Stuart H.
The price is CA $483
CA $782 total
includes taxes & fees
Oct 25 - Oct 26
3 Bed 3 Bath Home| Windsor| Parking - By Tempstay
A modern bedroom with a large bed, two bedside tables, and wall art.

17. Nr Legoland/Ascot.Comfy House.Ample Parking.Upto 8

Nr Legoland/Ascot.Comfy House.Ample Parking.Upto 8
Slough
10.0 out of 10, Exceptional, (1 review)
"Could not fault this place we have stayed in some expensive hotels and this beat those hands down. Amazing value. "
United Kingdom
david b.
The price is CA $370
CA $539 total
includes taxes & fees
Oct 11 - Oct 12
Nr Legoland/Ascot.Comfy House.Ample Parking.Upto 8
A modern house with a patio, a garden with various plants, and a wooden deck.

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

Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire
3.0 star property
Wraysbury
10.0 out of 10, Exceptional, (1 review)
The price is CA $360
CA $488 total
includes taxes & fees
Oct 12 - Oct 13
Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire
A bedroom with a bed, two windows with shutters, a radiator, and a picture on the wall.

19. 5BR Home Near Windsor Castle & Legoland

5BR Home Near Windsor Castle & Legoland
Clewer North
The price is CA $660
CA $886 total
includes taxes & fees
Oct 26 - Oct 27
5BR Home Near Windsor Castle & Legoland
A modern kitchen with white cabinetry, a central island, bar stools, pendant lighting, and a view of the outside.

20. Spacious 5-Bed Home in Windsor By Tempstay

Spacious 5-Bed Home in Windsor By Tempstay
Windsor City Centre
Spacious 5-Bed Home in Windsor By Tempstay
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

Radisson Hotel & Conference Centre London Heathrow

Radisson Hotel & Conference Centre London Heathrow

10/10 Excellent
"It was a good stay for preflight departures"
Danielle 1-night trip
Posted 2 hours ago
Radisson Hotel & Conference Centre London Heathrow

Find out more about Maidenhead

Maidenhead Vacation Homes information

Number of reviews
36
Accommodation
1317 Vacation Homes
Lowest Price
CA $373
Highest Price
CA $1,867