Windsor Holidays from £710

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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.
The Clocktower Hotel at Century House, Ascend Hotel Collection

The Clocktower Hotel at Century House, Ascend Hotel Collection

2.5 out of 5
per person
24 Sept - 30 Sept
found 21 hours ago
Return flight included
London (LGW) to Albany (ALB)
8.2/10 Very Good! (1,013 reviews)
Could be cleaned better ( nose and finger prints by peep hole on door, table in dining room dirty and broken). Also the time date were way off on the TV

Reviewed on 10 Aug 2025

Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
per person
24 Sept - 30 Sept
found 21 hours ago
Return flight included
London (LGW) to Albany (ALB)
8/10 Very Good! (1,159 reviews)
It is a comfortable location close to the airport. Plenty of parking. The property is well maintained. Bar/restaurant on the premises is average.

Reviewed on 9 Aug 2025

DoubleTree by Hilton Schenectady Downtown

DoubleTree by Hilton Schenectady Downtown

4 out of 5
Seward Place
per person
24 Sept - 30 Sept
found 21 hours ago
Return flight included
London (LGW) to Albany (ALB)
8.4/10 Very Good! (673 reviews)
Comfortable and clean.

Reviewed on 6 Aug 2025

La Quinta Inn & Suites by Wyndham Latham Albany Airport

La Quinta Inn & Suites by Wyndham Latham Albany Airport

3 out of 5
per person
24 Sept - 30 Sept
found 21 hours ago
Return flight included
London (LGW) to Albany (ALB)
7.4/10 Good! (1,000 reviews)
No hot water in the sinks, rust in tub area, keys didn’t work properly

Reviewed on 4 Aug 2025

Renaissance Albany Hotel

Renaissance Albany Hotel

3.5 out of 5
Downtown Albany
per person
24 Sept - 30 Sept
found 21 hours ago
Return flight included
London (LGW) to Albany (ALB)
9.2/10 Wonderful! (946 reviews)
Th property was good. We just didn’t like to area.

Reviewed on 7 Aug 2025

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

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is £98 per night from 27 Aug to 28 Aug
£98
27 Aug - 28 Aug
includes taxes & fees
8.6/10 Excellent! (1,938 reviews)
"This Vacation Village is amazing, returning this week for a little time away. Stayed last week for work and came home and planned a 3 day trip based on the location."

Reviewed on 10 Aug 2025

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is £80 per night from 7 Sept to 8 Sept
£80
7 Sept - 8 Sept
includes taxes & fees
8.8/10 Excellent! (546 reviews)
"Incredible spacious suites"

Reviewed on 6 Aug 2025

Berkshire Mountain Lodge
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is £55 per night from 27 Aug to 28 Aug
£55
27 Aug - 28 Aug
includes taxes & fees
5.2/10 (764 reviews)
"This family is professional and kind. I left a $100 tip because I watched attend to her guests and her two Autistic sons as well as her elderly parent. Amazing"

Reviewed on 2 Aug 2025

FairBridge Inn Express
See all 979 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 £710, 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.