We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Windsor and Maidenhead Vacation Rentals

Destination
Revenue impacts this sort order. Learn more

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
292 rentals in Windsor and Maidenhead.
The Old Wharf Cottage - Riverside Living with Private Pool, vacation rental in Windsor and Maidenhead
The Old Wharf Cottage - Riverside Living with Private Pool, vacation rental in Windsor and Maidenhead
The Old Wharf Cottage - Riverside Living with Private Pool, vacation rental in Windsor and Maidenhead

The Old Wharf Cottage - Riverside Living with Private Pool

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
A magical and romantic getaway near Windsor Castle and beside Windsor Great Park, vacation rental in Windsor and Maidenhead
A magical and romantic getaway near Windsor Castle and beside Windsor Great Park, vacation rental in Windsor and Maidenhead
A magical and romantic getaway near Windsor Castle and beside Windsor Great Park, vacation rental in Windsor and Maidenhead

A magical and romantic getaway near Windsor Castle and beside Windsor Great Park

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Gorgeous Country Cottage beside Windsor Great Park & overlooking Windsor Castle, vacation rental in Windsor and Maidenhead
Gorgeous Country Cottage beside Windsor Great Park & overlooking Windsor Castle, vacation rental in Windsor and Maidenhead
Gorgeous Country Cottage beside Windsor Great Park & overlooking Windsor Castle, vacation rental in Windsor and Maidenhead

Gorgeous Country Cottage beside Windsor Great Park & overlooking Windsor Castle

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Thieves Garden - Serviced, Self Catering Apartment, vacation rental in Windsor and Maidenhead
Thieves Garden - Serviced, Self Catering Apartment, vacation rental in Windsor and Maidenhead
Thieves Garden - Serviced, Self Catering Apartment, vacation rental in Windsor and Maidenhead

Thieves Garden - Serviced, Self Catering Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
2 double bedroom modern house with secure parking, vacation rental in Windsor and Maidenhead
2 double bedroom modern house with secure parking, vacation rental in Windsor and Maidenhead
2 double bedroom modern house with secure parking, vacation rental in Windsor and Maidenhead

2 double bedroom modern house with secure parking

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
 1 bedroom Cottage 5, sleeps 2/3, , vacation rental in Windsor and Maidenhead
 1 bedroom Cottage 5, sleeps 2/3, , vacation rental in Windsor and Maidenhead
 1 bedroom Cottage 5, sleeps 2/3, , vacation rental in Windsor and Maidenhead

1 bedroom Cottage 5, sleeps 2/3,

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Windsor, 3 Bedroom House, Sleeps 5 people, vacation rental in Windsor and Maidenhead
Windsor, 3 Bedroom House, Sleeps 5 people, vacation rental in Windsor and Maidenhead
Windsor, 3 Bedroom House, Sleeps 5 people, vacation rental in Windsor and Maidenhead

Windsor, 3 Bedroom House, Sleeps 5 people

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
King Edward IV Luxury Apartment , vacation rental in Windsor and Maidenhead
King Edward IV Luxury Apartment , vacation rental in Windsor and Maidenhead
King Edward IV Luxury Apartment , vacation rental in Windsor and Maidenhead

King Edward IV Luxury Apartment

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
King Edward III Luxury Windsor Apartments, vacation rental in Windsor and Maidenhead
King Edward III Luxury Windsor Apartments, vacation rental in Windsor and Maidenhead
King Edward III Luxury Windsor Apartments, vacation rental in Windsor and Maidenhead

King Edward III Luxury Windsor Apartments

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Studio Cottage 1, sleeps 2, Sheephouse Manor, vacation rental in Windsor and Maidenhead
Studio Cottage 1, sleeps 2, Sheephouse Manor, vacation rental in Windsor and Maidenhead
Studio Cottage 1, sleeps 2, Sheephouse Manor, vacation rental in Windsor and Maidenhead

Studio Cottage 1, sleeps 2, Sheephouse Manor

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
3 bed appt, sleeps 6, West Wing Sheephouse Manor, vacation rental in Windsor and Maidenhead
3 bed appt, sleeps 6, West Wing Sheephouse Manor, vacation rental in Windsor and Maidenhead
3 bed appt, sleeps 6, West Wing Sheephouse Manor, vacation rental in Windsor and Maidenhead

3 bed appt, sleeps 6, West Wing Sheephouse Manor

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
9 The Courtyard, Windsor, vacation rental in Windsor and Maidenhead
9 The Courtyard, Windsor, vacation rental in Windsor and Maidenhead
9 The Courtyard, Windsor, vacation rental in Windsor and Maidenhead

9 The Courtyard, Windsor

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Studio Apartment, Cottage 4, sleeps 2 plus child, vacation rental in Windsor and Maidenhead
Studio Apartment, Cottage 4, sleeps 2 plus child, vacation rental in Windsor and Maidenhead
Studio Apartment, Cottage 4, sleeps 2 plus child, vacation rental in Windsor and Maidenhead

Studio Apartment, Cottage 4, sleeps 2 plus child

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Alder House Serviced Apartment Maidenhead by Ferndale - Apt A, vacation rental in Windsor and Maidenhead
Alder House Serviced Apartment Maidenhead by Ferndale - Apt A, vacation rental in Windsor and Maidenhead
Alder House Serviced Apartment Maidenhead by Ferndale - Apt A, vacation rental in Windsor and Maidenhead

Alder House Serviced Apartment Maidenhead by Ferndale - Apt A

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Luxury Townhouse next to Windsor Castle, vacation rental in Windsor and Maidenhead
Luxury Townhouse next to Windsor Castle, vacation rental in Windsor and Maidenhead
Luxury Townhouse next to Windsor Castle, vacation rental in Windsor and Maidenhead

Luxury Townhouse next to Windsor Castle

Rental Home
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
The Clockhouse - Romantic Getaway Cottage Windsor, vacation rental in Windsor and Maidenhead
The Clockhouse - Romantic Getaway Cottage Windsor, vacation rental in Windsor and Maidenhead
The Clockhouse - Romantic Getaway Cottage Windsor, vacation rental in Windsor and Maidenhead

The Clockhouse - Romantic Getaway Cottage Windsor

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Stylish modern 2 bedroom apartment in Windsor, vacation rental in Windsor and Maidenhead
Stylish modern 2 bedroom apartment in Windsor, vacation rental in Windsor and Maidenhead
Stylish modern 2 bedroom apartment in Windsor, vacation rental in Windsor and Maidenhead

Stylish modern 2 bedroom apartment in Windsor

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
The Loft Windsor/Central Windsor/Free Parking, vacation rental in Windsor and Maidenhead
The Loft Windsor/Central Windsor/Free Parking, vacation rental in Windsor and Maidenhead
The Loft Windsor/Central Windsor/Free Parking, vacation rental in Windsor and Maidenhead

The Loft Windsor/Central Windsor/Free Parking

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
1 bedroom, Cottage 3, Sheephouse Manor, vacation rental in Windsor and Maidenhead
1 bedroom, Cottage 3, Sheephouse Manor, vacation rental in Windsor and Maidenhead
1 bedroom, Cottage 3, Sheephouse Manor, vacation rental in Windsor and Maidenhead

1 bedroom, Cottage 3, Sheephouse Manor

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Luxury Apartment on Eton High Street, vacation rental in Windsor and Maidenhead
Luxury Apartment on Eton High Street, vacation rental in Windsor and Maidenhead
Luxury Apartment on Eton High Street, vacation rental in Windsor and Maidenhead

Luxury Apartment on Eton High Street

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Period Cottage in the center of Windsor, vacation rental in Windsor and Maidenhead
Period Cottage in the center of Windsor, vacation rental in Windsor and Maidenhead
Period Cottage in the center of Windsor, vacation rental in Windsor and Maidenhead

Period Cottage in the center of Windsor

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Eton College Apartment, vacation rental in Windsor and Maidenhead
Eton College Apartment, vacation rental in Windsor and Maidenhead
Eton College Apartment, vacation rental in Windsor and Maidenhead

Eton College Apartment

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
2 bedroom, Cottage 2, Sheephouse Manor, , vacation rental in Windsor and Maidenhead
2 bedroom, Cottage 2, Sheephouse Manor, , vacation rental in Windsor and Maidenhead
2 bedroom, Cottage 2, Sheephouse Manor, , vacation rental in Windsor and Maidenhead

2 bedroom, Cottage 2, Sheephouse Manor,

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Stunning flat in quiet surroundings, 10 min walk to Ascot Racecourse, vacation rental in Windsor and Maidenhead
Stunning flat in quiet surroundings, 10 min walk to Ascot Racecourse, vacation rental in Windsor and Maidenhead
Stunning flat in quiet surroundings, 10 min walk to Ascot Racecourse, vacation rental in Windsor and Maidenhead

Stunning flat in quiet surroundings, 10 min walk to Ascot Racecourse

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
THE OLD SCHOOL HOUSE, ASCOT, BERKSHIRE, vacation rental in Windsor and Maidenhead
THE OLD SCHOOL HOUSE, ASCOT, BERKSHIRE, vacation rental in Windsor and Maidenhead
THE OLD SCHOOL HOUSE, ASCOT, BERKSHIRE, vacation rental in Windsor and Maidenhead

THE OLD SCHOOL HOUSE, ASCOT, BERKSHIRE

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Ascot - Spacious 2 bed  apartment ideal for Business or Leisure, vacation rental in Windsor and Maidenhead
Ascot - Spacious 2 bed  apartment ideal for Business or Leisure, vacation rental in Windsor and Maidenhead
Ascot - Spacious 2 bed  apartment ideal for Business or Leisure, vacation rental in Windsor and Maidenhead

Ascot - Spacious 2 bed apartment ideal for Business or Leisure

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Gorgeous Country Cottage, beside Windsor Great Park & overlooking Windsor Castle, vacation rental in Windsor and Maidenhead
Gorgeous Country Cottage, beside Windsor Great Park & overlooking Windsor Castle, vacation rental in Windsor and Maidenhead
Gorgeous Country Cottage, beside Windsor Great Park & overlooking Windsor Castle, vacation rental in Windsor and Maidenhead

Gorgeous Country Cottage, beside Windsor Great Park & overlooking Windsor Castle

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Lovely Flat With Parking In The Centre Of Royal Windsor, vacation rental in Windsor and Maidenhead
Lovely Flat With Parking In The Centre Of Royal Windsor, vacation rental in Windsor and Maidenhead
Lovely Flat With Parking In The Centre Of Royal Windsor, vacation rental in Windsor and Maidenhead

Lovely Flat With Parking In The Centre Of Royal Windsor

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Entire Loft with two double Bedrooms and en-suite Bathroom, vacation rental in Windsor and Maidenhead
Entire Loft with two double Bedrooms and en-suite Bathroom, vacation rental in Windsor and Maidenhead
Entire Loft with two double Bedrooms and en-suite Bathroom, vacation rental in Windsor and Maidenhead

Entire Loft with two double Bedrooms and en-suite Bathroom

Private Room
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Duke Street B&B, vacation rental in Windsor and Maidenhead
Duke Street B&B, vacation rental in Windsor and Maidenhead
Duke Street B&B, vacation rental in Windsor and Maidenhead

Duke Street B&B

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Showing results 1-30 of 292
Frequently Asked Questions about Windsor and Maidenhead