Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
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    Better together
    Save up to NZ$545 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Our pick of the best 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 NZ$217 per night from 24 Jun to 25 Jun
NZ$217
per night
24 Jun - 25 Jun
9/10 Wonderful! (268 reviews)
One night away with kids
"Wonderful little get away with the family - the hotel was lovely, we had a great breakfast and a hike across the street at Kennedy Park."

Reviewed on 20 Jun. 2024

Life House Berkshires
Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is NZ$272 per night from 23 Jun to 24 Jun
NZ$272
per night
23 Jun - 24 Jun
8.4/10 Very Good! (930 reviews)
Nifty hotel in a great little town
"The room was clean and distinctive. Everything worked properly. The hotel is perfectly located for accessing anything in town by foot, including MassMOCA and various eateries."

Reviewed on 16 Jun. 2024

Hotel Downstreet
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 NZ$228 per night from 26 Jun to 27 Jun
NZ$228
per night
26 Jun - 27 Jun
9/10 Wonderful! (1,001 reviews)
Pleasantly surprised
"We had a good experience here! The staff was AWESOME! They were very helpful in checking in and gave us good info. They have a bar but it was not open during the times we were in and out. The breakfast was good and we enjoyed the omelet. Its only on the weekend--wish it was every day! The pool was ..."

Reviewed on 15 Jun. 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 holiday package cost?
Starting from an incredible , you can customize your Windsor holiday 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 holiday 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 holiday?
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 travelling 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 holiday homes like mountain cabins and city residences. You’ve got choices galore!
Can I choose my airline with a Windsor Expedia holiday 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 holiday package?
Whether it’s your flight or hotel, you can cancel and rebook it. Booked your Windsor holiday 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.