Windsor Trips (flight + hotel)

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Top hotels in Windsor

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 P8,569 per night from Jul 20 to Jul 21
P8,569
P9,571 total
Jul 20 - Jul 21
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"Very cute hotel. The room was huge and the staff were friendly."

Reviewed on Jun 29, 2025

Hotel Downstreet, Ascend Hotel Collection
Vacation Village in the Berkshires
Vacation Village in the Berkshires
3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
8.6/10 Excellent! (1,843 reviews)
"amazing for the price and overall SOOO clean"

Reviewed on Jun 28, 2025

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Vacation Village in the Berkshires
The Williams Inn
The Williams Inn
4 out of 5
101 Spring Street, Williamstown, MA
The price is P13,926 per night from Jul 9 to Jul 10
P13,926
P15,555 total
Jul 9 - Jul 10
includes taxes & fees
9.6/10 Exceptional! (458 reviews)
"Wonderful stay. Helpful, professional staff."

Reviewed on Jun 27, 2025

The Williams Inn
See all 966 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.