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 ₩150,511 per night from Aug 28 to Aug 29
₩150,511
₩183,363 total
Aug 28 - Aug 29
includes taxes & fees
8.6/10 Excellent! (1,971 reviews)
"The property was very well maintained. Our room was very spacious and nice and clean. We did not receive any room service during our stay, We did end up running out of toilet paper and clean towels and had to walk all the way to the front desk which wasn’t attached to our building, a little inconvenient ..."

Reviewed on Aug 25, 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 ₩106,652 per night from Sep 7 to Sep 8
₩106,652
₩150,172 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (593 reviews)
"One of the best places we have stayed. The suite was well appointed, roomy, 2 TVs, full modern kitchen, huge bathroom, comfortable bed and linens. Large windows that actually open. Most of all the front desk staff was efficient, welcoming, and friendly."

Reviewed on Aug 25, 2025

Berkshire Mountain Lodge
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is ₩199,603 per night from Sep 25 to Sep 26
₩199,603
₩222,956 total
Sep 25 - Sep 26
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"Good value."

Reviewed on Aug 25, 2025

Hotel Downstreet, Ascend Hotel Collection
See all 965 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 many days is enough for Windsor?
The ideal length for your Windsor vacation 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 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.

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