Windsor Vacations

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Find the Best Windsor Vacation Packages

Windsor Hotel Deals

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 AED 437 per night from Mar 17 to Mar 18
AED 437
AED 520 total
includes taxes & fees
17 Mar - 18 Mar
8.6/10 Excellent! (1,784 reviews)
"It was very nice. Had a kitchen and 2 tvs!"

Reviewed on 7 March 2025

Vacation Village in the Berkshires
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AED 355 per night from Mar 27 to Mar 28
AED 355
AED 397 total
includes taxes & fees
27 Mar - 28 Mar
9/10 Wonderful! (524 reviews)
"For a small motel, it is very nice, I thought I was just paying for a cheap motel and got a quaint stay with a great mattress"

Reviewed on 12 March 2025

Life House Berkshires
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AED 309 per night from Mar 27 to Mar 28
AED 309
AED 345 total
includes taxes & fees
27 Mar - 28 Mar
9/10 Wonderful! (1,001 reviews)
Great Stay After or Before Shredding the Gnar!
"We came to shred the gnar at the Bousquet ski area down the block. This property is extremely convenient for such an endeavor. Check in was easy. There was exquisite artwork depicting the authentic Berkshire skiing experience in the room. The breakfast was radical. Eggs and sausages and muffins and ..."

Reviewed on 13 March 2025

The Yankee, Trademark Collection by Wyndham
See all 935 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 vacation package cost?
Offering great value package deals on Expedia, you’ll be surprised at how little a vacation 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 vacation packages and you could score some great off-season discounts.
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 vacation package as early as possible.
Is it cheaper to book a Windsor vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and stays separately. Better still, you can customize 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 vacation package to Windsor?
If you’ve got your Windsor vacation 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 accommodations and airfare: After you’ve nailed down your travel dates and duration, book the right Windsor vacation package for you.