Compare Windsor Vacation Rentals

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Windsor Rentals

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

1.88 mi from city center
This vacation home is a smoke-free vacation home.
Air conditioning
Parking available
Cozy apartment in charming Hartford with AC, WiFi

Cozy apartment in charming Hartford with AC, WiFi

6.1 mi from city center
$150 nightly
The price is $170 total per night
$170 total
Jul 13 - Jul 14
Total includes taxes and fees
At this apartment, guests have access to features like laundry facilities.
Washer
Dryer
Lux Boutique Large Private LOFT Pratt St Hartford

Lux Boutique Large Private LOFT Pratt St Hartford

6.1 mi from city center
$174 nightly
The price is $197 total per night
$197 total
Aug 1 - Aug 2
Total includes taxes and fees
At this apartment, guests have access to features like laundry facilities.
Kitchen
Washer
Mountaintop Horse Farm with Heated Pool

Mountaintop Horse Farm with Heated Pool

7.03 mi from city center
At this vacation home, guests have access to an outdoor pool, local meal delivery service, and a water dispenser. This smoke-free vacation home also has a garden.
Pool
Kitchen
Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.

Have the perfect stay in a cozy studio, nestled in the heart of Broad Brook.

2 out of 5
6.76 mi from city center
$154 nightly
The price is $174 total per night
$174 total
Jul 7 - Jul 8
Total includes taxes and fees
At this apartment, guests have access to barbecue grills.
Kitchen
Pet friendly
Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

Upscaled Home In A Quiet Neighborhood! You Have the Entire Home to Yourself!

16.24 mi from city center
$290 nightly
The price is $329 total per night
$329 total
Jul 31 - Aug 1
Total includes taxes and fees
This vacation home offers a water park, a gym, and laundry facilities. Other amenities at this family-friendly vacation home include a garden and barbecue grills.
Kitchen
Washer
Bring Your Pet & Visit Springfield: Westfield Home

Bring Your Pet & Visit Springfield: Westfield Home

2 out of 5
19.91 mi from city center
At this vacation home, guests have access to a garden.
Kitchen
Pet friendly
HOMEY HOMEY

HOMEY HOMEY

19.18 mi from city center
$147 nightly
The price is $167 total per night
$167 total
Jul 7 - Jul 8
Total includes taxes and fees
This apartment is a smoke-free apartment building.
Free WiFi
Air conditioning
PICON COZY

PICON COZY

19.18 mi from city center
$143 nightly
The price is $162 total per night
$162 total
Jul 7 - Jul 8
Total includes taxes and fees
At this vacation home, guests have access to features like laundry facilities.
Kitchen
Dryer
Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

16.74 mi from city center
$385 nightly
The price is $436 total per night
$436 total
Jul 21 - Jul 22
Total includes taxes and fees
At this vacation home, guests have access to an arcade/game room, laundry facilities, and a garden. This beach vacation home also has barbecue grills.
Kitchen
Washer
Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires

22.93 mi from city center
$344 nightly
The price is $364 total per night
$364 total
Jul 10 - Jul 11
Total includes taxes and fees
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Charming Chicopee Getaway

Charming Chicopee Getaway

21.03 mi from city center
$258 nightly
The price is $301 total per night
$301 total
Jul 7 - Jul 8
Total includes taxes and fees
At this apartment, guests have access to a garden.
Kitchen
Pet friendly
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Windsor Large Group Rentals

How to Book Vacation Rentals in Windsor



🏠 What is the best price for Windsor vacation rentals?

Windsor vacation rentals range in price, starting at $162 per night.


🏠 What types of vacation rentals in Windsor can I rent?

Orbitz offers a wide range of Windsor rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Windsor condo rentals.


🏠 Is it free to cancel my Windsor vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Windsor vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Windsor. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Windsor?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Windsor apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Windsor?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Windsor package deals will get you even more savings.

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