Windsor Trips (flight + hotel)

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    Save up to P 3,118 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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    Plan, book, and manage your trip all in one place

Top hotels in Windsor

Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is P6,814 per night from 3 Dec to 4 Dec
P6,814
P7,611 total
includes taxes & fees
Dec 3 - Dec 4
8.6/10 Excellent! (1,003 reviews)
"Great location, wonderful staff, fun pool and cool art. Would definitely stay again!"

Reviewed on Nov 15, 2024

Hotel Downstreet
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 P7,025 per night from 21 Nov to 22 Nov
P7,025
P7,847 total
includes taxes & fees
Nov 21 - Nov 22
9/10 Wonderful! (441 reviews)
"Loved the stay, only two things kept me from saying it was 5 stars. The WiFi connection was spotty so if you were watching tv (because they use Apple TV) it was freezing every 2 mins. Also, you can’t lower the room temp passed 65 and their 65 wasn’t a normal 65. It was still really warm. Besides ..."

Reviewed on Nov 17, 2024

Life House Berkshires
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is P5,487 per night from 26 Nov to 27 Nov
P5,487
P6,129 total
includes taxes & fees
Nov 26 - Nov 27
9/10 Wonderful! (1,005 reviews)
"Very friendly service, highly recommended!"

Reviewed on Nov 17, 2024

The Yankee, Trademark Collection by Wyndham
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.

Frequently asked questions

How much does a Windsor vacation package cost?
Starting from an incredible , 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.