Windsor Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $775 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Your Windsor Vacation

Enjoy amazing adventures when you reserve a Windsor vacation package. Whether you're a history buff, foodie or just a traveler who loves discovering new places, there's something for everyone in this awesome city. If seeing the sights is a priority during your trip to Windsor, make sure you swing by popular attractions like Wahconah Falls State Park and Bas Ridge Golf Course. No matter your travel plans or the size of your budget, organizing a tailored Windsor vacation is a walk in the park with Expedia.

Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Manchester View

The Manchester View

2.5 out of 5
per person
Dec. 13 - Dec. 17
found 7 hours ago
Roundtrip flight included
Detroit (DTW) to Albany (ALB)
9.4/10 Exceptional! (616 reviews)
Beautiful Views.. nice quiet place to stay

Reviewed on Sep. 18, 2024

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
per person
Dec. 13 - Dec. 17
found 7 hours ago
Roundtrip flight included
Detroit (DTW) to Albany (ALB)
7.4/10 Good! (403 reviews)
We loved the property and the staff was excellent.

Reviewed on Sep. 22, 2024

South Shire

South Shire

4 out of 5
per person
Dec. 13 - Dec. 17
found 7 hours ago
Roundtrip flight included
Detroit (DTW) to Albany (ALB)
9.4/10 Exceptional! (68 reviews)
Lovely Victorian building. The owner was wonderful! We’ll be back!

Reviewed on Aug. 16, 2024

Pinnacle Lodge

Pinnacle Lodge

2 out of 5
per person
Dec. 13 - Dec. 17
found 7 hours ago
Roundtrip flight included
Detroit (DTW) to Albany (ALB)
10/10 Exceptional! (1 review)

Ready to book your vacation to Windsor?

 

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Windsor Hotel Deals

Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Sep. 24 to Sep. 25
CA $172
CA $192 total
includes taxes & fees
Sep 24 - Sep 25
9/10 Wonderful! (396 reviews)
"Outdoor patio is nice. Surrounding area is beautiful. Things to see and do along with several restaurants and cafes."

Reviewed on Sep. 17, 2024

Life House Berkshires
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is CA $311 per night from Oct. 1 to Oct. 2
CA $311
CA $408 total
includes taxes & fees
Oct 1 - Oct 2
8.8/10 Excellent! (989 reviews)
"Lovely old hotel with excellent bar and restaurant. Central to all Berkshire sights. Room clean and well-appointed; wonderful shower; lobby and many nooks in which to curl up with drink and a good book… Ambassador felines Jane and Jack make Red Lion Inn feel like home."

Reviewed on Sep. 18, 2024

The Red Lion Inn
Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is CA $152 per night from Sep. 29 to Sep. 30
CA $152
CA $169 total
includes taxes & fees
Sep 29 - Sep 30
8.6/10 Excellent! (1,002 reviews)
Gorgeous place .
"Everything was wonderful in our room and the hotel itself. Beautiful views very comfortable room very quiet."

Reviewed on Sep. 18, 2024

Hotel Downstreet
See all 881 properties in Windsor
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Windsor vacation package cost?
Starting from an incredible CA $972, you can customize your Windsor vacation package. Simply bundle flights, hotels and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Windsor?
Browse and lock in everything all in one place with our Windsor vacation packages. You’ll find deals on hotels, flights and more that’ll keep your pocketbook happy and your adventurous spirit busy. And, with more than 550 partner airlines and 1,000,000 hotel options throughout the world to select from, you have countless opportunities to mix and match as you want.
How far in advance should I book my Windsor vacation?
While not all airlines advertise tickets early, customers are usually able to look up international fares on Expedia up to 12 months in advance. This is the time when you can nab some incredible bargains. If you’ve left everything to the last minute, you may still be in luck. Sometimes the lowest prices appear a few weeks prior to departure.
What does an Expedia Windsor travel package include?
It comes down to what you want. If you’re traveling by yourself, you might decide to combine hotels and flights. Bringing the whole crew to Windsor? A travel package that includes hotels, flights and rental cars might be a better fit. Expedia gives you the flexibility and freedom to customize your travel package.
What should I know before booking a Windsor travel package?
Booking all the parts of your trip together is a terrific way to save. Bundle your flights, car rentals and hotels into a tidy package. But you’re not restricted to hotels. Expedia offers all kinds of properties, including vacation rentals like mountain cabins and city residences. You’ve got choices galore!
Can I choose my airline with a Windsor Expedia vacation package?
You can, and with over 550 airlines to select from worldwide, you have plenty of choice. Scroll through the available options and see which airline fits your needs and budget.
If I'm not able to travel, can I cancel my Windsor vacation package?
Whether it’s your flight or hotel, you can cancel and rebook it. Booked your Windsor vacation package in the last 24 hours? You may be able to make changes or cancellations at no cost. If it’s been longer than that, you may incur a fee from your airline, hotel or car rental company. For more details, take a look at our Customer Service Portal. We’ll help you each step of the way.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.