Find Vacation Rentals in Windsor

We have 1,951 properties to choose from
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Popular Windsor Vacation Rentals

Find the perfect Windsor vacation rental

House Windsor
from $226 per night
House ∙ 6 guests ∙ 3 bedrooms

812 m² House

5.0
Outstanding(6 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Vrbo
Details
Apartment Windsor
from $187 per night
Apartment ∙ 4 guests ∙ 2 bedrooms

60 m² Apartment

5.0
Outstanding(10 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Vrbo
Details
Apartment Windsor
from $191 per night
2 guests ∙ 2 bedrooms

Apartment

5.0
Outstanding(4 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Vrbo
Details
Cottage Windsor
from $447 per night
6 guests ∙ 3 bedrooms

Cottage

5.0
Outstanding(6 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Vrbo
Details
House Windsor
from $380 per night
9 guests ∙ 6 bedrooms

House

4.5
Excellent(18 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Vrbo
Details
Apartment Windsor
from $105 per night
7 guests ∙ 3 bedrooms

Apartment

5.0
Outstanding(10 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Vrbo
Details
House Windsor
from $204 per night
House ∙ 6 guests ∙ 3 bedrooms

812 m² House

4.6
Excellent(11 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Vrbo
Details
House Windsor
from $95 per night
2 guests ∙ 1 bedroom

House

Windsor, Windsor and Maidenhead, United Kingdom
Vrbo
Details
Cottage Windsor
from $396 per night
6 guests ∙ 3 bedrooms

Cottage

5.0
Outstanding(116 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Vrbo
Details
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Vacation rentals with Wi-Fi

House  Windsor
from $420 per night
8 guests ∙ 4 bedrooms

House

5.0
Outstanding(17 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Internet
Vrbo
Details
House  Windsor
from $287 per night
House ∙ 21 guests ∙ 3 bedrooms

177 m² House

4.9
Outstanding(26 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Internet
Vrbo
Details
Cottage  Windsor
from $396 per night
6 guests ∙ 3 bedrooms

Cottage

5.0
Outstanding(117 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Internet
Vrbo
Details
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Apartments and vacation rentals with a kitchen

Apartment  Windsor
from $293 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

180 m² Apartment

5.0
Outstanding(10 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Kitchen
Vrbo
Details
House  Windsor
from $204 per night
House ∙ 6 guests ∙ 3 bedrooms

812 m² House

4.6
Excellent(11 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Kitchen
Vrbo
Details
House  Windsor
from $238 per night
8 guests ∙ 3 bedrooms

House

Windsor, Windsor and Maidenhead, United Kingdom
Kitchen
Vrbo
Details
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Vacation homes and rentals with a yard

House  Windsor
from $474 per night
House ∙ 10 guests ∙ 5 bedrooms

149 m² House

Windsor, Windsor and Maidenhead, United Kingdom
Yard
HomeToGo
Details
Apartment  Windsor
from $203 per night
2 guests ∙ 1 bedroom

Apartment

5.0
Outstanding(172 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Yard
HomeToGo
Details
Apartment  Windsor
from $361 per night
Apartment ∙ 2 guests ∙ 1 bedroom

46 m² Apartment

5.0
Outstanding(172 ratings)
Windsor, Windsor and Maidenhead, United Kingdom
Yard
HomeToGo
Details
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Frequently Asked Questions

How much does a night in a vacation rental cost in Windsor on average?

Prices for a stay in Windsor begin at $95 per night.

Is there a wide selection of vacation rentals in Windsor?

You can find 1,951 available vacation rentals in Windsor.

Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Vacation Rentals in Windsor

Save hundreds with a vacation home rental from Tripping.com and forget the hotel room. For the ultimate getaway, Windsor offers 294 affordable vacation rentals with a price to match your budget and accommodation needs. Prices in Windsor start at an average price of $185 a night with long-term rentals averaging $25 a month. These vacation rentals offer a range of amenities, so you’ll feel right at home. For those looking to stay in a corporate rental, 266 of Windsor’s rentals offer high speed WiFi Internet so you can easily keep in touch with your company or team. Go for a swim at one of the 10 properties complete with pool or jacuzzi, or relax with a night of cable TV in any of our 233 vacation home rentals. Traveling with your dog or cat? Choose from 27 pet-friendly rentals in Windsor that allow you to bring your extended family along.Tripping.com’s home rentals offer far more room and comfort than a hotel, providing a safe and spacious place for you and your pets. Many properties allow you to book directly online, so once you find that perfect vacation rental, you’ll be all set to go! Search properties from 6 vacation rental sites in Windsor where the top providers in that area are Booking.com, TripAdvisor, and Expedia. There are 110 Booking.com rentals, 71 TripAdvisor short term rentals and 47 Expedia vacation rentals.

Popular Day Trips Near Windsor

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