Windsor Holidays from £559
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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.
Top Windsor Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Oak 'n Spruce Resort
£559
per person
17 Nov - 22 Nov
found 22 hours ago
Return flight included
London (LHR) to Albany (ALB)
9.2/10 Wonderful! (989 reviews)
Very nice property excellent to stay with family. Especially if you have little ones with you. Property was clean well maintained. Helpful professional staff.
Reviewed on 28 Sept 2026
Hideaway Inn Lenox
£723
per person
17 Nov - 22 Nov
found 22 hours ago
Return flight included
London (LHR) to Albany (ALB)
7.8/10 Good! (60 reviews)
Easy check in, but a bit different since there is no staff to help check in. Had to find things on your own, but that was not difficult. Outside furniture could use and upgrade as our friends almost fell through the chair. But is was wonderful being able to sit outside, have appetizers, and play a game or just relax. All other guests we ran into were nice. I would return.
Reviewed on 18 Sept 2026
The Whitlock
£696
per person
17 Nov - 22 Nov
found 22 hours ago
Return flight included
London (LHR) to Albany (ALB)
8.4/10 Very good! (385 reviews)
The hotel staff were very friendly and helpful. There is ample parking and the location in town is great for walking to shops and restaurants. This is a very nice property.
Reviewed on 25 Sept 2026
Windsor Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 890 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Barrington Stage Company, Colonial Theatre and Berkshire Museum |
Top hotels in Windsor
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
£89
29 Sept - 30 Sept
includes taxes & fees
8.8/10 Excellent! (2,683 reviews)
"The temperature in the bedroom was very cold"
Reviewed on 28 Sept 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
£84
1 Oct - 2 Oct
includes taxes & fees
9/10 Wonderful! (1,160 reviews)
"The problem with the suites is that the cooking smell of the adjoining kitchen can really permeate throughout the entire space. So whoever cooked like a tomato sauce or something before I was there, I could really smell it in the bedroom. The bed was very comfortable though. The room was clean. The ..."
Reviewed on 28 Sept 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
£91
27 Oct - 28 Oct
includes taxes & fees
9.2/10 Wonderful! (1,015 reviews)
"Breakfast was good. Biggest issue was the TV. Thanks to a guest and Geoywho helped me. No documents in the room to explain how to use remote/ TV"
Reviewed on 28 Sept 2026
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 travel package cost?
Our Windsor packages, which begin from just £559, 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.
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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. Flight-inclusive packages are ATOL protected.
