Taos Valley Accommodations - Vacation Rentals in Windsor and Maidenhead

The Bakehouse Guesthouse From US $68
         

9.7 (56 Reviews)
House
  • Parking
  • Designated Smoking Area
  • Internet
Radiant Penthouse on the Banks of the Thames - Pass the Keys From US $752
         

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10.0 (13 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Accessibility
Large 4BR Home, 2 Baths, Castle Views From US $220
         

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10.0 (7 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Windsor Castle 4-Bed & Garden From US $543
         

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10.0 (4 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Luxury Eton Cottage-Design Led From US $366
         

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10.0 (4 Reviews)
Villa
  • Parking
  • View
  • Accessibility
Super Chic Apartment in Beautiful Sunninghill - Pass the Keys From US $270
         

Eton, Windsor - 1 Bedroom First Floor Apartment - Parking From US $166
         

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10.0 (4 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Accessibility

Luxury Places to Stay in Windsor and Maidenhead

Over 361+ Luxury Places to Stay in or Near Windsor and Maidenhead
Closest Home to Windsor Castle From US $5,575
         

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9.5 (2 Reviews)
House
  • Parking
  • View
  • Balcony/Terrace
Gleneagles From US $3,721
         

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New
House
  • Parking
  • Pool
  • View
3 Bed in Bray oc-s32608 From US $2,620
         

New
House
  • Parking
  • View
  • Security/Safety

Top-Rated Vacation Rentals with a Pool in Windsor and Maidenhead

Over 10+ Top-Rated Vacation Rentals with a Pool in or Near Windsor and Maidenhead
Coworth Park - Dorchester Collection From US $669
         

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9.5 (324 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
The Inn On The Green From US $199
         

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8.8 (464 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Sheephouse Manor From US $99
         

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8.4 (39 Reviews)
House
  • Parking
  • Pet Friendly
  • Pool
LEGOLAND(R) Windsor Resort From US $415
         

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8.0 (555 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
De Vere Beaumont Estate From US $154
         

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7.7 (5288 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • Pool
Macdonald Berystede Hotel & Spa From US $180
         

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7.3 (2473 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • Pool
Fredrick's Hotel & Spa From US $145
         

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6.2 (841 Reviews)
Hotel
  • Parking
  • Pool
  • Designated Smoking Area

Pet-Friendly Vacation Rentals in Windsor and Maidenhead

Over 78+ Pet-Friendly Vacation Rentals in or Near Windsor and Maidenhead
Heart of Windsor Private Garden, Free Parking & Stylish 3BR Home From US $340
         

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10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • Designated Smoking Area
Garden, Driveway, Private, Nr Windsor & Great Park From US $224
         

Cozy 2BR apartment in Maidenhead Sleeps 6 From US $116
         

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10.0 (1 Review)
Apartment
  • Parking
  • Pet Friendly
  • Transportation/Shuttle
Amazing Central Windsor Flat Contractors welcome From US $185
         

9.7 (4 Reviews)
Villa
  • Parking
  • Pet Friendly
  • Security/Safety
The Garden Cabin From US $151
         

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9.6 (39 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • Designated Smoking Area

Large Vacation Homes & Villas in Windsor and Maidenhead

Over 50+ Large Vacation Homes & Villas in or Near Windsor and Maidenhead
Luxury 6-Bed 6-Bath Home Near LEGOLAND with Parking From US $783
         

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10.0 (3 Reviews)
House
  • Parking
  • Designated Smoking Area
  • View
Charming Cottage in Old Windsor - Near Heathrow Airport & Lego Land From US $229
         

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10.0 (2 Reviews)
Apartment
  • Parking
  • Security/Safety
  • Business Services
Clarence House-Windsor-Parking-5 bed From US $441
         

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9.8 (19 Reviews)
Villa
  • Parking
  • View
  • Balcony/Terrace
Leworth Apartments, Windsor From US $272
         

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9.7 (100 Reviews)
Apartment
  • Security/Safety
  • Fireplace/Heating
  • Child Friendly
Windsor/Legoland/Ascot charming 3BR home in centre From US $353
         

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9.6 (15 Reviews)
Villa
  • Parking
  • View
  • Security/Safety
Legoland Family HQ - 6-Bed Retreat - Sleeps 15 From US $639
         

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9.5 (2 Reviews)
Villa
  • Parking
  • Pet Friendly
  • View
Windsorian Experience From US $164
         

9.4 (1156 Reviews)
House
  • Parking
  • Designated Smoking Area
  • TV
Park Farm From US $162
         

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9.4 (572 Reviews)
Bed & Breakfast
  • Parking
  • Balcony/Terrace
  • Security/Safety

Wheelchair Accessible Vacation Homes in Windsor and Maidenhead

Over 15+ Wheelchair Accessible Vacation Homes in or Near Windsor and Maidenhead
Charming Victorian House w Parking River Walks - Pass the Keys From US $742
         

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9.2 (12 Reviews)
House
  • Parking
  • View
  • Wheelchair Accessible
Royal Retreat & Lego Lodge with free parking From US $273
         

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7.6 (109 Reviews)
House
  • Parking
  • Pet Friendly
  • Designated Smoking Area
Harte & Garter From US $140
         

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7.0 (2126 Reviews)
Apartment
  • Parking
  • Designated Smoking Area
  • Wheelchair Accessible
Hurley House Hotel From US $314
         

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9.5 (124 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
The Christopher Hotel, Eton From US $179
         

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9.1 (3029 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • Designated Smoking Area
Holiday Inn Express Windsor by IHG From US $172
         

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8.8 (514 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Monkey Island Estate - Small Luxury Hotels of the World From US $1,170
         

The Royal Foresters, Ascot, Berkshire - Acorn Pubs From US $133
         

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8.7 (678 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible

Windsor and Maidenhead Vacation Rentals and Airbnb Places to Stay Under $200

Over 104+ Windsor and Maidenhead Vacation Rentals and Airbnb Places to Stay Under $200
Russell Street - Studio by Accommodation Windsor From US $129
         

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10.0 (2 Reviews)
Apartment
  • Parking
  • Security/Safety
  • Sports/Activities
Stunning 2BR flat with balcony From US $182
         

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10.0 (1 Review)
Apartment
  • Accessibility
  • Security/Safety
  • Fireplace/Heating
Maidenhead - Gated Parking Balcony From US $165
         

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10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Security/Safety
Modern Maidenhead Retreat, 3Bed, 1 Bath From US $160
         

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10.0 (1 Review)
Apartment
  • Parking
  • View
  • Security/Safety
Windsor Flat 90C From US $142
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Spacious 2-Bedroom Apartments in Windsor CH From US $136
         

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10.0 (1 Review)
Apartment
  • View
  • Security/Safety
  • Sports/Activities
Spacious, Newly Renovated Flat in Charming Village From US $130
         

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10.0 (1 Review)
Apartment
  • Parking
  • Security/Safety
  • Sports/Activities

About Windsor and Maidenhead Vacation Rentals

With more than 370 Windsor and Maidenhead vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Taos Valley and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Windsor and Maidenhead.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Taos Valley Windsor and Maidenhead, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Windsor and Maidenhead. Places to stay near Windsor and Maidenhead are 1089.09 ft² on average, with prices averaging US $370 a night.

Taos Valley makes it easy and safe to find and compare vacation rentals in Windsor and Maidenhead with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Windsor and Maidenhead

Type Count
Holiday Apartments 178
Vacation Homes 147
Hotels 28
Villas 9
B&B 5
Ski Chalet Rentals 1

Use these Quick Filters to Find a Vacation Rental in Windsor and Maidenhead

Pro Tip: Taos Valley makes it easy to compare the best listings on Taos Valley homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Taos Valley homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Windsor and Maidenhead.

Weather in Windsor and Maidenhead

View the weather forecast for Windsor and Maidenhead before booking your Windsor and Maidenhead Vacation Rentals to confirm your best time to go.

December - February
High 43°F       Low 32°F
March - May
High 61°F       Low 36°F
June - August
High 63°F       Low 48°F
September - November
High 58°F       Low 35°F

Windsor and Maidenhead Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Windsor and Maidenhead?
How many vacation rentals have private pools in Windsor and Maidenhead?

There are 1 vacation rentals with private pools near Windsor and Maidenhead. Top-rated homes that have access to a swimming pool include:

How many vacation rentals are available in Windsor and Maidenhead?

Currently, the total number of properties listed in 2026 is over 370 in the Windsor and Maidenhead area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Windsor and Maidenhead.