Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to £335 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

Your Windsor Holiday

Enjoy amazing adventures when you reserve a Windsor holiday package. Whether you're a history buff, foodie or just a traveller 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, organising a tailored Windsor holiday is a walk in the park with Expedia.

Our pick of the best Windsor Hotel Deals

Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,830 reviews)
"second time stayed here. Love it!"

Reviewed on 20 Jun 2025

Vacation Village in the Berkshires
Red Roof Inn PLUS+ South Deerfield – Amherst
Red Roof Inn PLUS+ South Deerfield – Amherst
2.5 out of 5
9 Greenfield Rd, South Deerfield, MA
Stay at this hotel in South Deerfield. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their ...
7/10 Good! (1,003 reviews)
"Good Location"

Reviewed on 16 Jun 2025

Red Roof Inn PLUS+ South Deerfield – Amherst
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business centre and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (659 reviews)
Good for a girls trip!
"We loved the comfortable beds and ensuite bathrooms. The kitchen was well-equipped and common room was comfortable too. We didn't use any of the other amenities, but there were quite a few options that looked appealing. Convenient to Lenox which was our primary destination for dining and ..."

Reviewed on 21 Jun 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
See all 967 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

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Windsor travel package cost?
Our Windsor packages, which begin from just , are an awesome way to save money. Pick and choose your preferred flights, hotels and rental cars to create a customized itinerary.
If I'm not able to travel, can I cancel my Windsor travel package?
You can cancel your Windsor booking if your plans have been upended. Whether you'll incur a penalty or not depends on your airline, hotel or car rental company. You may be able to change or cancel free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.
How do I get a cheap travel package to Windsor?
You'll save tons of cash if you combine your car rentals, hotels and flights into a Windsor travel package. Sometimes cheap means fewer choices. But not with Expedia. We offer more than 550 air carriers and 1,000,000 hotels worldwide, so you'll always have plenty of variety to choose from. Like to save even more? Add some exciting activities to your package deal and unlock even bigger discounts! After all, travel is about more than simply getting to your destination.
Does Expedia offer Book Now, Pay Later Windsor holidays?
We do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your trip in instalments. Simply choose the payment plan that works for you during the checkout process and take away the stress of budgeting for your trip. Be sure to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your buck. Check out our flexible payment options below:
  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's manageable monthly instalment plans. If making bite-sized repayments each month works for you, choose this option during the checkout process.
  • Pay in instalments holidays: If you'd prefer to pay off your getaway across multiple transactions, holidays paid in instalments might be the best option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Clicking the "book now" button is much easier with this payment option. Just put down a small deposit on your holiday and then get on your way.

What are the top hotels in Windsor?
Lock in a room at Holiday Village In The Berkshires. It's one of the neighbourhood's most in-demand properties. Another reputable option in Windsor is The Black Swan Lee - Lenox, Ascend Hotel Collection.
How far in advance should I book my Windsor holiday?
Savvy travellers often book early. You can normally compare international airfares on Expedia up to a year before your intended flight. If you've left booking to the last minute, there's no need to worry. Bargain prices occasionally appear just weeks before departure dates.
What does an Expedia Windsor travel package include?
Hotels, flights and rental cars, or any combination of the three --- it's totally up to you. Whether you're headed to Windsor with the kids or enjoying a solo break, there's a package to fit every style and budget. Once you've made your booking, why not add on a couple of tours or activities?
What should I know before booking a Windsor travel package?
You can look forward to saving with an Expedia travel package. Combine your airfares, rental cars and hotels and be rewarded with fabulous discounts. Hotels aren't your only choice, though. We have beachside condos, chalets in the middle of mountains and everything in between!
Can I choose my airline with a Windsor Expedia travel package?
Yes --- that's the beauty of an Expedia package. You can mix and match your flights, hotels and more. We have access to more than 550 partner airlines globally, so you have loads of choice when organising your Windsor escape.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.