Airport Express Hotel - Vacation Rentals in Windsor and Maidenhead

Macdonald Windsor Hotel From US $126
         

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New
Hotel
  • Air Conditioner
  • Wheelchair Accessible
  • Bedding/Linens
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 $247
         

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9.8 (83 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Standard Single Room - Shared From US $67
         

New
Hotel
  • Security/Safety
  • Child Friendly
Coworth Park - Dorchester Collection From US $669
         

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9.4 (325 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Coworth Park - Dorchester Collection From US $736
         

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9.6 (197 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Bel and The Dragon-Cookham From US $163
         

9.0 (490 Reviews)
Hotel
  • Parking
  • Pet Friendly
  • View
Bel & The Dragon Cookham From US $138
         

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9.2 (349 Reviews)
Hotel
  • Balcony/Terrace
  • Security/Safety
  • Business Services

Luxury Places to Stay in Windsor and Maidenhead

Over 1105+ Luxury Places to Stay in or Near Windsor and Maidenhead
Gleneagles From US $10,530
         

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New
Cottage
  • Parking
  • Pool
  • Balcony/Terrace
Closest Home to Windsor Castle From US $5,575
         

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New
House
  • Parking
  • Balcony/Terrace
  • Security/Safety
Gleneagles From US $3,721
         

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New
House
  • Parking
  • Pool
  • View
Coventina From US $3,200
         

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New
Cottage
  • Parking
  • Pet Friendly
  • Balcony/Terrace

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

Over 33+ Top-Rated Vacation Rentals with a Pool in or Near Windsor and Maidenhead
Country House (East Wing) with Indoor Heated Pool From US $1,355
         

10.0 (6 Reviews)
House
  • Parking
  • Pool
  • Designated Smoking Area
Quaint bungalow with Swimming Pool and lovely garden From US $285
         

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

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8.8 (438 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
LEGOLAND Windsor Resort From US $181
         

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8.4 (229 Reviews)
Hotel
  • Parking
  • Pool
  • Designated Smoking Area

Pet-Friendly Vacation Rentals in Windsor and Maidenhead

Over 213+ Pet-Friendly Vacation Rentals in or Near Windsor and Maidenhead
Gorgeous Country Cottage, beside Windsor Great Park & overlooking Windsor Castle From US $530
         

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
  • Parking
  • Pet Friendly
  • Balcony/Terrace
Imperial Court by Viridian Apartments From US $166
         

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7.2 (7 Reviews)
Apartment
  • Parking
  • Pet Friendly
  • TV
4 Bed Windsor Countryside Escape - By Tempstay From US $579
         

Large Vacation Homes & Villas in Windsor and Maidenhead

Over 118+ Large Vacation Homes & Villas in or Near Windsor and Maidenhead
Historic River View Home in Windsor - By Tempstay From US $1,431
         

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 $719
         

Dual-Property Retreat in Windsor - By Tempstay From US $1,680
         

Executive Getaway | 6BR House Close to Legoland From US $722
         

10.0 (1 Review)
House
  • Parking
  • TV
  • Balcony/Terrace
Spacious 5 bed Sunninghill W/Drive - By Tempstay From US $448
         

Wheelchair Accessible Vacation Homes in Windsor and Maidenhead

Over 68+ Wheelchair Accessible Vacation Homes in or Near Windsor and Maidenhead
Central Windsor Apartment Facing The Castle From US $288
         

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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9.1 (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
2 Bed Penthouse in Windsor - VAT Q - By Tempstay From US $382
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
2BR Penthouse |Cinema Room|Parking - By Tempstay From US $371
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Charming 2 Bed Apt | Windsor - VAT Q - By Tempstay From US $300
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Host & Stay | Thames Apartment From US $290
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Wheelchair Accessible
Romantic Luxury Shepherd’s Hut (Wagon) near London & Windsor From US $275
         

10.0 (1 Review)
Cabin
  • Parking
  • Designated Smoking Area
  • View

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

Over 282+ Windsor and Maidenhead Vacation Rentals and Airbnb Places to Stay Under $200
THE OLD SCHOOL HOUSE, ASCOT, BERKSHIRE From US $128
         

10.0 (51 Reviews)
Cottage
  • Parking
  • Designated Smoking Area
  • TV
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 $192
         

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9.8 (200 Reviews)
Bed & Breakfast
  • Parking
  • TV
  • Accessibility
Chic Studio Steps from Windsor Castle From US $170
         

10.0 (1 Review)
Apartment
  • Parking
  • TV
  • Security/Safety
1BR Apartment | Walk to Shops & Castle From US $192
         

9.0 (2 Reviews)
Apartment
  • Parking
  • TV
  • Security/Safety

Instantly Bookable Vacation Homes in Windsor and Maidenhead

Over 433+ 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 $496
         

10.0 (15 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace
Immaculate Central Windsor Town House From US $439
         

10.0 (15 Reviews)
House
  • Parking
  • TV
  • Security/Safety
Lovely 2-bedroom apartment, free parking & garden From US $344
         

10.0 (7 Reviews)
Apartment
  • Parking
  • TV
  • Balcony/Terrace
2 Bed Apt| Parking| Central Windsor By Tempstay From US $319
         

Crown Mews, including parking Windsor Centre From US $337
         

10.0 (5 Reviews)
House
  • Parking
  • TV
  • Security/Safety

About Windsor and Maidenhead Vacation Rentals

With more than 62 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 111.84 ft² on average, with prices averaging US $188 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 61
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:

Which vacation homes in Windsor and Maidenhead are best for families?

If you are looking for a family-friendly vacation home in Windsor and Maidenhead, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying 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 62 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.