Windsor Holidays from £881

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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

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    Windsor Hotel Deals

    Hotel On North

    A building entrance with a large planter with purple flowers and a small tree.
    • Address: 297 North Street, Pittsfield, MA, 01201, US
    • Location: 11.2 mi from Windsor
    • Star rating: 3.5/5
    • Guest rating: 9.6/10 (Exceptional, 985 reviews)
    • Price: £98, includes taxes & fees, 29 Nov - 30 Nov

    Rodeway Inn

    A hotel room with a bed, two bedside lamps, a chair, a dresser, a mirror, and a painting on the wall.
    • Address: 99 Howland Ave, Adams, MA, 01220, US
    • Location: 10.3 mi from Windsor
    • Star rating: 2/5
    • Guest rating: 7.4/10 (Good, 285 reviews)
    • Price: £55, includes taxes & fees, 14 Dec - 15 Dec

    FairBridge Inn Express

    A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.
    • Address: 16 Cheshire Road, Pittsfield, MA, 01201, US
    • Location: 8.5 mi from Windsor
    • Star rating: 2.5/5
    • Guest rating: 5.4/10 (937 reviews)
    • Price: £60, includes taxes & fees, 16 Nov - 17 Nov

    The Revival House

    A living room with a fireplace, two sofas, and four black side tables.
    • Address: 17 Commercial St, Adams, MA, 01220, US
    • Location: 8.5 mi from Windsor
    • Star rating: 3/5
    • Guest rating: 9/10 (Wonderful, 46 reviews)
    • Price: £117, includes taxes & fees, 24 Nov - 25 Nov
    • Review: Nice historic, Inn like feeling. Comfy rooms, easy breakfast until 1pm!! Staff responsive via SMS almost 24/7

    Howard Johnson by Wyndham Lenox

    A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
    • Address: 462 Pittsfield Rd, Lenox, MA, 01240, US
    • Location: 13.4 mi from Windsor
    • Star rating: 2/5
    • Guest rating: 7.6/10 (Good, 938 reviews)
    • Price: £67, includes taxes & fees, 16 Nov - 17 Nov

    The Yankee Inn

    Two Adirondack chairs facing a river with a forested hill in the background.
    • Address: 461 Pittsfield Rd, Lenox, MA, 01240, US
    • Location: 13.5 mi from Windsor
    • Star rating: 2.5/5
    • Guest rating: 9.2/10 (Wonderful, 1004 reviews)
    • Price: £107, includes taxes & fees, 12 Dec - 13 Dec
    • Review: Everything about this place was wonderful! The location, the staff, the cleanliness. The only downsize was we booked this property because of the pool and it was under maintenance during my stay. A notice would have been nice :( Other than that, beautiful inn.

    Berkshire Mountain Lodge

    A large building with a prominent tower, surrounded by trees and a winding road.
    • Address: 8 Dan Fox Dr, Pittsfield, MA, 01201, US
    • Location: 13 mi from Windsor
    • Star rating: 3/5
    • Guest rating: 9/10 (Wonderful, 1273 reviews)
    • Price: £82, includes taxes & fees, 6 Dec - 7 Dec
    • Review: Handy to have an apartment style room for a multi night stay. Convenient location and nice amenities. Good value and balance of amenities and price

    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.

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    Frequently Asked Questions

    How much does a Windsor travel package cost?

    Our Windsor packages, which begin from just £881, 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.

    Explore a world of travel with Expedia

    * Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.