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 SAR 418 per night from Jun 8 to Jun 9
SAR 418
SAR 508 total
8 Jun - 9 Jun
includes taxes & fees
8.6/10 Excellent! (1,815 reviews)
"Children on the floor above ran around and it was very loud for about three hours while we were trying to go to sleep. The rooms were as advertised. Staff was friendly and helpful."

Reviewed on 1 June 2025

Vacation Village in the 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 SAR 434 per night from Jun 17 to Jun 18
SAR 434
SAR 484 total
17 Jun - 18 Jun
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Friendly staff"

Reviewed on 7 June 2025

The Yankee, Trademark Collection by Wyndham
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
Fully refundable
The price is SAR 484 per night from Jun 8 to Jun 9
SAR 484
SAR 593 total
8 Jun - 9 Jun
includes taxes & fees
9/10 Wonderful! (644 reviews)
"Best way to spend a long needed weekend. Can’t wait to do a full week."

Reviewed on 2 June 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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 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.