Airport Express Hotel - Vacation Rentals in Windsor and Maidenhead

Standard Single Room - Shared From US $69
         

New
Hotel
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  • Child Friendly
Hurley House Hotel From US $314
         

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9.5 (124 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Hurley House Hotel From US $279
         

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9.8 (80 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Macdonald Windsor Hotel From US $126
         

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New
Hotel
  • Air Conditioner
  • Wheelchair Accessible
  • Bedding/Linens
Coworth Park - Dorchester Collection From US $829
         

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9.4 (276 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Coworth Park - Dorchester Collection From US $655
         

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9.6 (193 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Bel and The Dragon-Cookham From US $163
         

9.0 (486 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • View
Bel & The Dragon Cookham From US $121
         

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9.2 (344 Reviews)
Hotel
  • Balcony/Terrace
  • Security/Safety
  • Business Services

Luxury Places to Stay in Windsor and Maidenhead

Over 1078+ Luxury Places to Stay in or Near Windsor and Maidenhead
Gleneagles From US $10,530
         

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New
Cottage
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Gleneagles From US $3,721
         

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New
House
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  • Pool
  • View
Coventina From US $3,181
         

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New
Cottage
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Shreem Homes! Charming home in Wraysbury! From US $2,676
         

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

Over 27+ Top-Rated Vacation Rentals with a Pool in or Near Windsor and Maidenhead
Quaint bungalow with Swimming Pool and lovely garden From US $290
         

10.0 (2 Reviews)
House
  • Pool
  • Security/Safety
  • Bedding/Linens
The Inn On The Green From US $199
         

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8.7 (395 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
LEGOLAND Windsor Resort From US $181
         

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8.4 (224 Reviews)
Hotel
  • Parking
  • Pool
  • Designated Smoking Area
De Vere Beaumont Estate From US $107
         

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8.0 (1005 Reviews)
Hotel
  • Parking
  • Pool
  • TV

Pet-Friendly Vacation Rentals in Windsor and Maidenhead

Over 205+ Pet-Friendly Vacation Rentals in or Near Windsor and Maidenhead
Gorgeous Country Cottage, beside Windsor Great Park & overlooking Windsor Castle From US $482
         

10.0 (106 Reviews)
Cottage
  • Parking
  • Pet Friendly
  • Designated Smoking Area
Cosy Central Windsor House Sleeps 4 From US $183
         

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8.6 (76 Reviews)
House
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  • Pet Friendly
  • Balcony/Terrace
Imperial Court by Viridian Apartments From US $166
         

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7.2 (7 Reviews)
Apartment
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  • Pet Friendly
  • TV
CHESTNUT COTTAGE ❤ WINDSOR COUNTRYSIDE ESCAPE From US $514
         

Cosy Family Home In Windsor, Close To Legoland From US $463
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Large Vacation Homes & Villas in Windsor and Maidenhead

Over 112+ Large Vacation Homes & Villas in or Near Windsor and Maidenhead
Historic River View Property in Windsor From US $976
         

10.0 (3 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace
Large 4BR Home, 2 Baths, Castle Views From US $220
         

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10.0 (4 Reviews)
House
  • Parking
  • Pet Friendly
  • View
Charming Victorian House w/Parking + River Walks - Pass the Keys From US $767
         

Charming Dual-Property Retreat in Windsor From US $1,710
         

10.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • TV
Spacious 5 bed Sunninghill with driveway parking From US $417
         

Wheelchair Accessible Vacation Homes in Windsor and Maidenhead

Over 66+ Wheelchair Accessible Vacation Homes in or Near Windsor and Maidenhead
Central Windsor Apartment Facing The Castle From US $294
         

8.6 (10 Reviews)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Charming Victorian House w Parking River Walks - Pass the Keys From US $742
         

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9.0 (11 Reviews)
House
  • Parking
  • View
  • Wheelchair Accessible
King Edward Apartments From US $320
         

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9.4 (68 Reviews)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
2BR Luxury Penthouse |Cinema Room|Private Parking - VAT Q From US $350
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Imperial Quarter Penthouse in Windsor - VAT Q From US $306
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Host & Stay | Thames Apartment From US $295
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Romantic Luxury Shepherd’s Hut (Wagon) near London & Windsor From US $280
         

10.0 (1 Review)
Cabin
  • Parking
  • Designated Smoking Area
  • View
Charming Two-Bedroom Apartment in Windsor - VAT Q From US $252
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible

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

Over 285+ Windsor and Maidenhead Vacation Rentals and Airbnb Places to Stay Under $200
Central Windsor House From US $87
         

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7.3 (57 Reviews)
House
  • Parking
  • Balcony/Terrace
  • Child Friendly
Park Farm Bed and Breakfast From US $139
         

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9.8 (194 Reviews)
Bed & Breakfast
  • Parking
  • TV
  • Accessibility
THE OLD SCHOOL HOUSE, ASCOT, BERKSHIRE From US $132
         

10.0 (51 Reviews)
Cottage
  • Parking
  • Designated Smoking Area
  • TV
1BR Apartment | Walk to Shops & Castle From US $169
         

10.0 (1 Review)
Apartment
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  • TV
  • Security/Safety
Chic Studio Steps from Windsor Castle From US $149
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Security/Safety

Instantly Bookable Vacation Homes in Windsor and Maidenhead

Over 405+ Instantly Bookable Vacation Homes in or Near Windsor and Maidenhead
haven Valley near the theme park From US $758
         

10.0 (1 Review)
House
  • Security/Safety
  • Bedding/Linens
  • Wellness Facilities
Relaxing guest house with Jacuzzi & boat hire From US $346
         

10.0 (17 Reviews)
Cabin
  • Parking
  • TV
  • Balcony/Terrace
Fabulous Central Windsor Town House From US $502
         

10.0 (15 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace
Immaculate Central Windsor Town House From US $388
         

10.0 (15 Reviews)
House
  • Parking
  • TV
  • Security/Safety
Lovely 2-bedroom apartment, free parking & garden From US $294
         

10.0 (7 Reviews)
Apartment
  • Parking
  • TV
  • Balcony/Terrace

About Windsor and Maidenhead Vacation Rentals

With more than 61 Windsor and Maidenhead vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Airportexpresshotel 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 Airportexpresshotel 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 113.68 ft² on average, with prices averaging $174 a night.

Airportexpresshotel 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
Hotels with Suites 60
Vacation Homes 1

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

Pro Tip: Airportexpresshotel makes it easy to compare the best listings on Airportexpresshotel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Airportexpresshotel 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?

There are a lot of options in Windsor and Maidenhead. If you plan on staying in the Windsor and Maidenhead area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Windsor and Maidenhead:

How many vacation rentals are available in Windsor and Maidenhead?

Currently, the total number of properties listed in 2026 is over 61 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.