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Windsor and Maidenhead Family & Kid Friendly Rentals

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172 rentals in Windsor and Maidenhead.
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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, Kid friendly
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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

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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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, Kid friendly
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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, Kid friendly
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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, Kid friendly
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Unique Five Bedroom Creek House on the Thames, vacation rental in Windsor and Maidenhead
Unique Five Bedroom Creek House on the Thames, vacation rental in Windsor and Maidenhead
Unique Five Bedroom Creek House on the Thames, vacation rental in Windsor and Maidenhead

Unique Five Bedroom Creek House on the Thames

Rental Home
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps, Kid friendly
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Open! Luxurious Eton / Windsor Thames Riverside getaway, vacation rental in Windsor and Maidenhead
Open! Luxurious Eton / Windsor Thames Riverside getaway, vacation rental in Windsor and Maidenhead
Open! Luxurious Eton / Windsor Thames Riverside getaway, vacation rental in Windsor and Maidenhead

Open! Luxurious Eton / Windsor Thames Riverside getaway

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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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, Kid friendly
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Beautiful Family Home in semi-rural location, 10 mins To Legoland, Sleeps 7, vacation rental in Windsor and Maidenhead
Beautiful Family Home in semi-rural location, 10 mins To Legoland, Sleeps 7, vacation rental in Windsor and Maidenhead
Beautiful Family Home in semi-rural location, 10 mins To Legoland, Sleeps 7, vacation rental in Windsor and Maidenhead

Beautiful Family Home in semi-rural location, 10 mins To Legoland, Sleeps 7

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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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, Kid friendly
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Unique open plan house in central Windsor pet friendly + parking, vacation rental in Windsor and Maidenhead
Unique open plan house in central Windsor pet friendly + parking, vacation rental in Windsor and Maidenhead
Unique open plan house in central Windsor pet friendly + parking, vacation rental in Windsor and Maidenhead

Unique open plan house in central Windsor pet friendly + parking

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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AMAZING LOCATION!! STAY RIGHT IN THE TOWN CENTRE - JUST STEPS FROM ALL AMENITIES, vacation rental in Windsor and Maidenhead
AMAZING LOCATION!! STAY RIGHT IN THE TOWN CENTRE - JUST STEPS FROM ALL AMENITIES, vacation rental in Windsor and Maidenhead
AMAZING LOCATION!! STAY RIGHT IN THE TOWN CENTRE - JUST STEPS FROM ALL AMENITIES, vacation rental in Windsor and Maidenhead

AMAZING LOCATION!! STAY RIGHT IN THE TOWN CENTRE - JUST STEPS FROM ALL AMENITIES

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Stylish house in Central Windsor, in quiet setting., vacation rental in Windsor and Maidenhead
Stylish house in Central Windsor, in quiet setting., vacation rental in Windsor and Maidenhead
Stylish house in Central Windsor, in quiet setting., vacation rental in Windsor and Maidenhead

Stylish house in Central Windsor, in quiet setting.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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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, Kid friendly
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Homely flat with castle view and parking, vacation rental in Windsor and Maidenhead
Homely flat with castle view and parking, vacation rental in Windsor and Maidenhead
Homely flat with castle view and parking, vacation rental in Windsor and Maidenhead

Homely flat with castle view and parking

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Fabulous house on the river Thames riverside, near Windsor and London, vacation rental in Windsor and Maidenhead
Fabulous house on the river Thames riverside, near Windsor and London, vacation rental in Windsor and Maidenhead
Fabulous house on the river Thames riverside, near Windsor and London, vacation rental in Windsor and Maidenhead

Fabulous house on the river Thames riverside, near Windsor and London

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps, Kid friendly
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ROYAL WINDSOR, RIVERSIDE, WI-FI, 4 BEDROOM FAMILY HOME,3 BATH, SLEEPS UPTO 7, vacation rental in Windsor and Maidenhead
ROYAL WINDSOR, RIVERSIDE, WI-FI, 4 BEDROOM FAMILY HOME,3 BATH, SLEEPS UPTO 7, vacation rental in Windsor and Maidenhead
ROYAL WINDSOR, RIVERSIDE, WI-FI, 4 BEDROOM FAMILY HOME,3 BATH, SLEEPS UPTO 7, vacation rental in Windsor and Maidenhead

ROYAL WINDSOR, RIVERSIDE, WI-FI, 4 BEDROOM FAMILY HOME,3 BATH, SLEEPS UPTO 7

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps, Kid friendly
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Stunning Eton Apartment

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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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, Kid friendly
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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, Kid friendly
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STABLE HOUSE ETON WINDSOR, vacation rental in Windsor and Maidenhead
STABLE HOUSE ETON WINDSOR, vacation rental in Windsor and Maidenhead
STABLE HOUSE ETON WINDSOR, vacation rental in Windsor and Maidenhead

STABLE HOUSE ETON WINDSOR

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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The Studio, Datchet, Windsor, vacation rental in Windsor and Maidenhead
The Studio, Datchet, Windsor, vacation rental in Windsor and Maidenhead
The Studio, Datchet, Windsor, vacation rental in Windsor and Maidenhead

The Studio, Datchet, Windsor

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps, Kid friendly
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Stunning Penthouse Apartment, vacation rental in Windsor and Maidenhead
Stunning Penthouse Apartment, vacation rental in Windsor and Maidenhead
Stunning Penthouse Apartment, vacation rental in Windsor and Maidenhead

Stunning Penthouse Apartment

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Riverside Bungalow near legoland, Windsor, Hot Tub & Sauna. Pet Friendly., vacation rental in Windsor and Maidenhead
Riverside Bungalow near legoland, Windsor, Hot Tub & Sauna. Pet Friendly., vacation rental in Windsor and Maidenhead
Riverside Bungalow near legoland, Windsor, Hot Tub & Sauna. Pet Friendly., vacation rental in Windsor and Maidenhead

Riverside Bungalow near legoland, Windsor, Hot Tub & Sauna. Pet Friendly.

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Hampden Apartments - The Diana, vacation rental in Windsor and Maidenhead
Hampden Apartments - The Diana, vacation rental in Windsor and Maidenhead
Hampden Apartments - The Diana, vacation rental in Windsor and Maidenhead

Hampden Apartments - The Diana

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Immaculate Central Windsor Town House, vacation rental in Windsor and Maidenhead
Immaculate Central Windsor Town House, vacation rental in Windsor and Maidenhead
Immaculate Central Windsor Town House, vacation rental in Windsor and Maidenhead

Immaculate Central Windsor Town House

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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STABLE HOUSE (HOUSE), vacation rental in Windsor and Maidenhead
STABLE HOUSE (HOUSE), vacation rental in Windsor and Maidenhead
STABLE HOUSE (HOUSE), vacation rental in Windsor and Maidenhead

STABLE HOUSE (HOUSE)

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
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Luxury Central Eton Cottage, 5 minute walk from Windsor Castle. FREE PARKING, vacation rental in Windsor and Maidenhead
Luxury Central Eton Cottage, 5 minute walk from Windsor Castle. FREE PARKING, vacation rental in Windsor and Maidenhead
Luxury Central Eton Cottage, 5 minute walk from Windsor Castle. FREE PARKING, vacation rental in Windsor and Maidenhead

Luxury Central Eton Cottage, 5 minute walk from Windsor Castle. FREE PARKING

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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The Loft Windsor is the perfect choice for business and leisure stays, vacation rental in Windsor and Maidenhead
The Loft Windsor is the perfect choice for business and leisure stays, vacation rental in Windsor and Maidenhead
The Loft Windsor is the perfect choice for business and leisure stays, vacation rental in Windsor and Maidenhead

The Loft Windsor is the perfect choice for business and leisure stays

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, Kid friendly
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Luxury Country Estate with Concierge and Staff. Close to London, Windsor, Ascot, vacation rental in Windsor and Maidenhead
Luxury Country Estate with Concierge and Staff. Close to London, Windsor, Ascot, vacation rental in Windsor and Maidenhead
Luxury Country Estate with Concierge and Staff. Close to London, Windsor, Ascot, vacation rental in Windsor and Maidenhead

Luxury Country Estate with Concierge and Staff. Close to London, Windsor, Ascot

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps, Kid friendly
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1 The Courtyard Apartments, High Street Windsor, vacation rental in Windsor and Maidenhead
1 The Courtyard Apartments, High Street Windsor, vacation rental in Windsor and Maidenhead
1 The Courtyard Apartments, High Street Windsor, vacation rental in Windsor and Maidenhead

1 The Courtyard Apartments, High Street Windsor

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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42 Trevelyan Court by Accommodation Windsor, vacation rental in Windsor and Maidenhead
42 Trevelyan Court by Accommodation Windsor, vacation rental in Windsor and Maidenhead
42 Trevelyan Court by Accommodation Windsor, vacation rental in Windsor and Maidenhead

42 Trevelyan Court by Accommodation Windsor

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Hampden Apartments - The Archie, vacation rental in Windsor and Maidenhead
Hampden Apartments - The Archie, vacation rental in Windsor and Maidenhead
Hampden Apartments - The Archie, vacation rental in Windsor and Maidenhead

Hampden Apartments - The Archie

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
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Clarence House - Luxury Accommodation, vacation rental in Windsor and Maidenhead
Clarence House - Luxury Accommodation, vacation rental in Windsor and Maidenhead
Clarence House - Luxury Accommodation, vacation rental in Windsor and Maidenhead

Clarence House - Luxury Accommodation

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
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Boutique  luxury apartment, Windsor, London , Heathrow, vacation rental in Windsor and Maidenhead
Boutique  luxury apartment, Windsor, London , Heathrow, vacation rental in Windsor and Maidenhead
Boutique  luxury apartment, Windsor, London , Heathrow, vacation rental in Windsor and Maidenhead

Boutique luxury apartment, Windsor, London , Heathrow

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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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, Kid friendly
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Clarence House - Windsor, vacation rental in Windsor and Maidenhead
Clarence House - Windsor, vacation rental in Windsor and Maidenhead
Clarence House - Windsor, vacation rental in Windsor and Maidenhead

Clarence House - Windsor

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Kid friendly
More info
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Windsor, 3 Bed house, free parking, close to Legoland + Thorpe Park, vacation rental in Windsor and Maidenhead
Windsor, 3 Bed house, free parking, close to Legoland + Thorpe Park, vacation rental in Windsor and Maidenhead
Windsor, 3 Bed house, free parking, close to Legoland + Thorpe Park, vacation rental in Windsor and Maidenhead

Windsor, 3 Bed house, free parking, close to Legoland + Thorpe Park

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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The Mulberry Luxury Flat - Town Centre| balcony | Free parking, vacation rental in Windsor and Maidenhead
The Mulberry Luxury Flat - Town Centre| balcony | Free parking, vacation rental in Windsor and Maidenhead
The Mulberry Luxury Flat - Town Centre| balcony | Free parking, vacation rental in Windsor and Maidenhead

The Mulberry Luxury Flat - Town Centre| balcony | Free parking

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Braywick Serviced Apartments by Ferndale Apt 06, vacation rental in Windsor and Maidenhead
Braywick Serviced Apartments by Ferndale Apt 06, vacation rental in Windsor and Maidenhead
Braywick Serviced Apartments by Ferndale Apt 06, vacation rental in Windsor and Maidenhead

Braywick Serviced Apartments by Ferndale Apt 06

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
More info
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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, Kid friendly
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 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, Kid friendly
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Welcome to our Boutique Private & Secluded Garden Studio., vacation rental in Windsor and Maidenhead
Welcome to our Boutique Private & Secluded Garden Studio., vacation rental in Windsor and Maidenhead
Welcome to our Boutique Private & Secluded Garden Studio., vacation rental in Windsor and Maidenhead

Welcome to our Boutique Private & Secluded Garden Studio.

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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Windsor Mews, In the heart of Windsor Town Centre with free Parking!!!, vacation rental in Windsor and Maidenhead
Windsor Mews, In the heart of Windsor Town Centre with free Parking!!!, vacation rental in Windsor and Maidenhead
Windsor Mews, In the heart of Windsor Town Centre with free Parking!!!, vacation rental in Windsor and Maidenhead

Windsor Mews, In the heart of Windsor Town Centre with free Parking!!!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, Kid friendly
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Windsor Studio - Luxury Apartment, vacation rental in Windsor and Maidenhead
Windsor Studio - Luxury Apartment, vacation rental in Windsor and Maidenhead
Windsor Studio - Luxury Apartment, vacation rental in Windsor and Maidenhead

Windsor Studio - Luxury Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, Kid friendly
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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, Kid friendly
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NEW - Fabulous location for families, converted stables, 5 mins to Legoland, vacation rental in Windsor and Maidenhead
NEW - Fabulous location for families, converted stables, 5 mins to Legoland, vacation rental in Windsor and Maidenhead
NEW - Fabulous location for families, converted stables, 5 mins to Legoland, vacation rental in Windsor and Maidenhead

NEW - Fabulous location for families, converted stables, 5 mins to Legoland

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Kid friendly
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5 Garfield Place, vacation rental in Windsor and Maidenhead
5 Garfield Place, vacation rental in Windsor and Maidenhead
5 Garfield Place, vacation rental in Windsor and Maidenhead

5 Garfield Place

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Kid friendly
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The Loft | Central Windsor | Sleeps 3, vacation rental in Windsor and Maidenhead
The Loft | Central Windsor | Sleeps 3, vacation rental in Windsor and Maidenhead
The Loft | Central Windsor | Sleeps 3, vacation rental in Windsor and Maidenhead

The Loft | Central Windsor | Sleeps 3

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, Kid friendly
More info
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Luxurious Eton Townhouse with Sunny garden, vacation rental in Windsor and Maidenhead
Luxurious Eton Townhouse with Sunny garden, vacation rental in Windsor and Maidenhead
Luxurious Eton Townhouse with Sunny garden, vacation rental in Windsor and Maidenhead

Luxurious Eton Townhouse with Sunny garden

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Kid friendly
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