Find Vacation Rentals in Windsor

We have 344 properties to choose from
Windsor
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Popular Windsor Vacation Rentals

Find the perfect Windsor vacation rental

House Windsor
e.g. 12/10 - 12/17 (Sat - Sat)
$177 per night
House ∙ 6 guests ∙ 3 bedrooms
Windsor, Windsor and Maidenhead, Atlantic Ocean
Details
HomeToGo
Details
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Apartment Windsor
e.g. 5/20 - 5/27 (Sat - Sat)
$287 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (1 rating)
Windsor, Windsor and Maidenhead, Atlantic Ocean
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Vrbo
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Details
Apartment Windsor
e.g. 12/17 - 12/24 (Sat - Sat)
-27%
$169
$123 per night
Apartment ∙ 3 guests ∙ 2 bedrooms
Windsor, Windsor and Maidenhead, Atlantic Ocean
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Vrbo
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Details
Apartment Windsor
e.g. 5/20 - 5/27 (Sat - Sat)
$235 per night
Apartment ∙ 4 guests ∙ 1 bedroom
5.0
"Excellent" (6 ratings)
Windsor, Windsor and Maidenhead, Atlantic Ocean
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Vrbo
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Details
Apartment Windsor
e.g. 12/17 - 12/24 (Sat - Sat)
$95 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Windsor, Windsor and Maidenhead, Atlantic Ocean
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Vrbo
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Details
Apartment Windsor
e.g. 6/6 - 6/13 (Tue - Tue)
$362 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (9 ratings)
Windsor, Windsor and Maidenhead, Atlantic Ocean
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Vrbo
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Details
Apartment Windsor
e.g. 5/20 - 5/27 (Sat - Sat)
$248 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Windsor, Windsor and Maidenhead, Atlantic Ocean
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Vrbo
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Details
House Windsor
e.g. 1/14 - 1/21 (Sat - Sat)
$155 per night
House ∙ 6 guests ∙ 3 bedrooms
Windsor, Windsor and Maidenhead, Atlantic Ocean
Details
HomeToGo
Details
Details
House Windsor
e.g. 5/20 - 5/27 (Sat - Sat)
$472 per night
House ∙ 6 guests ∙ 3 bedrooms
Windsor, Windsor and Maidenhead, Atlantic Ocean
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Vrbo
Details
Details
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Vacation rentals with Wi-Fi

House Internet Windsor
$237 per night
House ∙ 4 guests ∙ 2 bedrooms
4.8
"Excellent" (11 ratings)
Windsor, Windsor and Maidenhead, Atlantic Ocean
Internet
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Vrbo
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Apartment Internet Windsor
$120 per night
Apartment ∙ 3 guests ∙ 1 bedroom
4.6
"Outstanding" (5 ratings)
Windsor, Windsor and Maidenhead, Atlantic Ocean
Internet
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Vrbo
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Details
House Internet Windsor
$102 per night
House ∙ 5 guests ∙ 3 bedrooms
4.7
"Outstanding" (32 ratings)
Windsor, Windsor and Maidenhead, Atlantic Ocean
Internet
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Vrbo
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Details
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Vacation rentals and apartments with air conditioning

House Aircondition Windsor
$382 per night
House ∙ 7 guests ∙ 4 bedrooms
5.0
"Excellent" (12 ratings)
Windsor, Windsor and Maidenhead, Atlantic Ocean
Aircondition
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Vrbo
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Details
House Aircondition Windsor
$233 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0
"Excellent" (10 ratings)
Windsor, Windsor and Maidenhead, Atlantic Ocean
Aircondition
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Vrbo
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House Aircondition Windsor
$807 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (29 ratings)
Windsor, Windsor and Maidenhead, Atlantic Ocean
Aircondition
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Vrbo
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Best vacation rentals with a balcony

Apartment Balcony Windsor
$306 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
5.0
"Excellent" (2 ratings)
Windsor, Windsor and Maidenhead, Atlantic Ocean
Balcony
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Vrbo
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Details
House Balcony Windsor
$219 per night
House ∙ 7 guests ∙ 3 bedrooms
5.0
"Excellent" (9 ratings)
Windsor, Windsor and Maidenhead, Atlantic Ocean
Balcony
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Vrbo
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Details
Apartment Balcony Windsor
$313 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
5.0
"Excellent" (9 ratings)
Windsor, Windsor and Maidenhead, Atlantic Ocean
Balcony
Details
Vrbo
Details
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 $92 per night.

Is there a wide selection of vacation rentals in Windsor?

You can find 512 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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