Windsor Holidays

Book a Hotel + Flight or Car together to unlock savings

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 2.844.674 ₫ per night from 27 Aug to 28 Aug
2.844.674 ₫
3.465.596 ₫ total
27 Aug - 28 Aug
includes taxes & fees
8.6/10 Excellent! (1,943 reviews)
"Easy to get to, nice property. Lots of things to do and easy to communicate."

Reviewed on 13 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
8.8/10 Excellent! (554 reviews)
"It was a great stay. The couches in the room were dirty and should be replaced."

Reviewed on 11 Aug 2025

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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 1.864.597 ₫ per night from 26 Aug to 27 Aug
1.864.597 ₫
2.082.755 ₫ total
26 Aug - 27 Aug
includes taxes & fees
5.2/10 (766 reviews)
"The bathroom in our room looks like someone was murdered in the bathtub. There were stains on the bottom of the tub."

Reviewed on 10 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.

Frequently asked questions

How much does a Windsor holiday package cost?
Offering great value package deals on Expedia, you'll be surprised at how little a holiday to Windsor costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Windsor?
You can generally find lower rates and greater availability in January, February and March. Take a look at our cheap Windsor holiday packages and you could score some great off-season discounts.
How many days is enough for Windsor?
The ideal length for your Windsor holiday depends on what you'd like to do and see. Usually, a handful of days to a week will give you enough time to visit all the leading sights and explore some hidden treasures along the way.
How to find the best Windsor package deals?
Use Expedia's filter tool to find some unbeatable Windsor package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Windsor package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package as early as possible.
Is it cheaper to book a Windsor holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging flights and stays separately. Better still, you can customise your Windsor trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a holiday package to Windsor?
If you've got your Windsor holiday dates locked in, book early to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Windsor?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Windsor.
  2. Set a budget: Factor in expenses such as food, flights and transportation when working out how much to set aside for your trip to Windsor. Then, select a hotel that matches your budget, whether that's an economical option or a more upscale getaway.
  3. Work out your trip length: Think about how much time you'd like to spend exploring Windsor. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your accommodation and airfare: After you've nailed down your travel dates and duration, book the right Windsor holiday package for you.