Windsor and Maidenhead Vacation Rentals from ￥28,096: Search Short-Term Rentals

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Our top choices for Windsor and Maidenhead vacation rentals

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

1. Willow Court Farm

Windsor

Anne

￥28,096 total

includes taxes & fees

Sep 16 - Sep 17

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

￥30,747 total

includes taxes & fees

Sep 21 - Sep 22

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

￥31,926 total

includes taxes & fees

Sep 17 - Sep 18

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

4. Hampden Apartments - The William

Eton

Tony

￥29,974 total

includes taxes & fees

Sep 17 - Sep 18

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.

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

Eton

jennifer j.

￥35,732 total

includes taxes & fees

Sep 16 - Sep 17

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

6. Spacious, light apartment sleeps up to four

Cookham

Alexandra C.

￥43,835 total

includes taxes & fees

Sep 17 - Sep 18

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 City Centre

David T.

￥47,990 total

includes taxes & fees

Oct 1 - Oct 2

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

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

Windsor City Centre

Toni

￥37,703 total

includes taxes & fees

Sep 23 - Sep 24

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

9. Luxury 2 Bedroom Apartment

Clewer North

￥39,256 total

includes taxes & fees

Sep 20 - Sep 21

A bedroom with a bed, a desk, a chair, a window, and a balcony.

10. Hampden Apartments - The Edward

Windsor City Centre

david

￥28,428 total

includes taxes & fees

Sep 24 - Sep 25

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.

￥31,682 total

includes taxes & fees

Oct 12 - Oct 13

A balcony with two chairs and a table, a potted plant, and a view of buildings in the background.

12. Cosy Central Apartment in Windsor By Tempstay

Clewer East

Nick R.

￥36,012 total

includes taxes & fees

Sep 16 - Sep 17

13. 1BR Apartment | Walk to Shops & Castle

Windsor City Centre

Paula B.

￥28,746 total

includes taxes & fees

Oct 5 - Oct 6

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

14. 2BR House, Walk to Windsor Castle + Parking for 1

Windsor City Centre

Don K.

￥47,285 total

includes taxes & fees

Sep 16 - Sep 17

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

15. Windsor Home with Free Parking

Clewer South

Ian G.

￥35,525 total

includes taxes & fees

Sep 21 - Sep 22

16. 1BR Gem, Private Parking - VAT Q - By Tempstay

Clewer East

Anne J.

￥44,142 total

includes taxes & fees

Sep 17 - Sep 18

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

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

Cookham

Maggie L.

￥49,341 total

includes taxes & fees

Sep 19 - Sep 20

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

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

Wraysbury

￥53,803 total

includes taxes & fees

Sep 22 - Sep 23

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.

￥56,242 total

includes taxes & fees

Sep 20 - Sep 21

A modern bedroom with a bed, bedside lamp, and a window.

20. Central Windsor 1BR | Steps from Attractions

Windsor City Centre

Andrea W.

￥36,037 total

includes taxes & fees

Sep 16 - Sep 17

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Top Windsor and Maidenhead Hotel Reviews

Sir Christopher Wren Hotel

8/10 Good

"The central location makes up for the lack of empathy shown by the staff. They seem to be there under duress, certainly not to help guests. The bell boy was excellent and very helpful though. The parking is some way but if you have your key, you can use the back door which saves a few minutes. Breakfast is good and in an excellent location but the hotel lets itself down by the staff."

The Royal Adelaide Hotel

8/10 Good

"Excellent breakfast and engaging staff. Bathroom was a bit tired in terms of wear and tear and is crying out to be a walk in shower rather than a shower over a bath due to the closeness of the toilet to the side of the bath and the awkwardness of clambering into and out of the bath without the potential of slipping. Comfy bed and really clean room overall. Great walking distance to the town centre and across the road from the Long Walk on the Windsor Estate."

Holiday Inn Express Windsor by IHG

10/10 Excellent

"Great and convenient hotel at the other end of the high street in Windsor so everywhere was walkable. Appeared newly refurbished so rooms and communal spaces were well designed, clean and new. Very comfy beds and aircon and which was good as it was ever so humid the weekend we stayed. Great breakfast-I loved the pancake machine, the cooked breakfast bought out in sensible sized batches so was hot and fresh and whilst the coffee tasted great, the machine was surprisingly slow. Nice and bright area to sit with friends for breakfast. Staff were lovely and couldn’t have been more helpful and friendly."

Thames Riviera Hotel, Sure Hotel Collection by Best Western

10/10 Excellent

"The Thames Riviera Hotel is an older building with English Heritage listing which precludes the addition of more modern equipment such as a lift. This should be borne in mind if physically challenged by stairs, and there are quite a few to negotiate on to get to the upper floors. The building retains its period quirkiness such as upper floors that are not quite on the level, a feature of many older properties. Outside on the terrace is a great place to relax with a cocktail, beer or favourite beverage whilst watching the activities of the Maidenhead Rowing Club on the river. The service we received was excellent throughout our stay. Evening food was very good though not outstanding, but very reasonably priced. For those wishing to experience finer dining there are several alternatives close including Alain Roux's riverside brasserie just across the bridge. If looking to experience a break from the corporate one-size-fits-all hostelry offerings, the Best Western Thames Riviera is certainly worth considering."

Find out more about Windsor and Maidenhead

Vacation Apartments in Windsor and Maidenhead

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Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Windsor and Maidenhead vacation rentals

1. Willow Court Farm

2. The Fox at Hurley - Delightful Property!

3. Copper Castle & Petting Farm near Legoland

4. Hampden Apartments - The William

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

6. Spacious, light apartment sleeps up to four

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

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

9. Luxury 2 Bedroom Apartment

10. Hampden Apartments - The Edward

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

12. Cosy Central Apartment in Windsor By Tempstay

13. 1BR Apartment | Walk to Shops & Castle

14. 2BR House, Walk to Windsor Castle + Parking for 1

15. Windsor Home with Free Parking

16. 1BR Gem, Private Parking - VAT Q - By Tempstay

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

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

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

20. Central Windsor 1BR | Steps from Attractions

Find vacation rentals that suit your style

Top Windsor and Maidenhead Hotel Reviews

Sir Christopher Wren Hotel

Bisham Abbey National Sports Centre

De Vere Beaumont Estate

The Royal Adelaide Hotel

Oakley Court

Holiday Inn Express Windsor by IHG

Coworth Park - Dorchester Collection

Thames Riviera Hotel, Sure Hotel Collection by Best Western

The Olde Bell, BW Signature Collection

Find out more about Windsor and Maidenhead

Vacation Apartments in Windsor and Maidenhead

Vacation Rentals in Windsor and Maidenhead

Change your mind

Treat yourself

Be picky

Our top choices for Windsor and Maidenhead vacation rentals

1. Willow Court Farm

2. The Fox at Hurley - Delightful Property!

3. Copper Castle & Petting Farm near Legoland

4. Hampden Apartments - The William

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

6. Spacious, light apartment sleeps up to four

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

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

9. Luxury 2 Bedroom Apartment

10. Hampden Apartments - The Edward

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

12. Cosy Central Apartment in Windsor By Tempstay

13. 1BR Apartment | Walk to Shops & Castle

14. 2BR House, Walk to Windsor Castle + Parking for 1

15. Windsor Home with Free Parking

16. 1BR Gem, Private Parking - VAT Q - By Tempstay

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

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

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

20. Central Windsor 1BR | Steps from Attractions

Find vacation rentals that suit your style

Top Windsor and Maidenhead Hotel Reviews

Sir Christopher Wren Hotel

Find out more about Windsor and Maidenhead

Vacation Apartments in Windsor and Maidenhead