Windsor Holidays

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Your Windsor Holiday

Our holiday packages to Windsor let you customise your own adventure. Tailor your journey to your interests and style and make the most of your time in this interesting city. Want some sightseeing tips for your trip to Windsor? Wahconah Falls State Park and Bas Ridge Golf Course are two of the main attractions here. Whatever your travel plans or the size of your budget, organising a tailored Windsor holiday is a walk in the park with Expedia.

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Windsor Holiday

Windsor Essential Information

Language
English
Currency
U.S dollars
Population
890
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Berkshire Museum, Colonial Theatre and Barrington Stage Company

Our pick of the best Windsor Hotel Deals

Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is AU$199 per night from 22 Dec to 23 Dec
AU$199
includes taxes & fees
22 Dec - 23 Dec
8.6/10 Excellent! (999 reviews)
"Great location, wonderful staff, fun pool and cool art. Would definitely stay again!"

Reviewed on 15 Nov. 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 AU$205 per night from 25 Nov to 26 Nov
AU$205
includes taxes & fees
25 Nov - 26 Nov
9/10 Wonderful! (442 reviews)
"Staff were very friendly and the rooms were decorated adorably! We absolutely enjoyed our stay!"

Reviewed on 20 Nov. 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 AU$160 per night from 1 Dec to 2 Dec
AU$160
includes taxes & fees
1 Dec - 2 Dec
9/10 Wonderful! (1,001 reviews)
"Staff was very nice, friendly and accommodating. The room was nice, clean, comfortable and spacious."

Reviewed on 18 Nov. 2024

The Yankee, Trademark Collection by Wyndham
See all 883 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 Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

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.