Windsor Vacation Packages

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Your Windsor Vacation

Enjoy amazing adventures when you reserve a Windsor vacation package. Whether you're a history buff, foodie or just a traveler who loves discovering new places, there's something for everyone in this awesome city. If seeing the sights is a priority during your trip to Windsor, make sure you swing by popular attractions like Wahconah Falls State Park and Bas Ridge Golf Course. No matter your travel plans or the size of your budget, organizing a tailored Windsor vacation is a walk in the park with Expedia.

Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Berkshire Mountain Lodge
The Dewey
Vacation Village in the Berkshires
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Springs Motel

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Choose your dates

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 CA $118 per night from Jul 17 to Jul 18
CA $118
CA $147 total
Jul 17 - Jul 18
includes taxes & fees
8.6/10 Excellent! (1,873 reviews)
"I loved the pool for the kids, it a quiet place"

Reviewed on Jul. 13, 2025

Vacation Village in the Berkshires
Red Roof Inn PLUS+ South Deerfield – Amherst

Red Roof Inn PLUS+ South Deerfield – Amherst

2.5 out of 5
9 Greenfield Rd, South Deerfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Jul 31 to Aug 1
CA $159
CA $178 total
Jul 31 - Aug 1
includes taxes & fees
7/10 Good! (1,006 reviews)
"It was clean and served our purpose just fine"

Reviewed on Jul. 14, 2025

Red Roof Inn PLUS+ South Deerfield – Amherst
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
The price is CA $325 per night from Aug 11 to Aug 12
CA $325
CA $364 total
Aug 11 - Aug 12
includes taxes & fees
9.6/10 Exceptional! (467 reviews)
"Hrwat"

Reviewed on Jul. 11, 2025

The Williams Inn
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 from CA $427 on Expedia, you'll be pleasantly surprised at how much a vacation to Windsor costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Windsor?
You can typically find lower prices and greater availability in January, February and March. Explore our cheap Windsor vacation packages and you could land some great off-season discounts.
How many days is enough for Windsor?
With a well-organized itinerary, you can easily tick off the top Windsor attractions in a handful of days. But if you want to discover hidden gems or go on day trips, think about booking your Windsor vacation for longer.
How to find the best Windsor package deals?
Begin your search for a Windsor package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Windsor package deal straight away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Windsor adventure off to a flying start.
Is it cheaper to book a Windsor vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and stays individually. Better still, you can personalize your Windsor trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Windsor?
If you've got your Windsor travel dates locked in, book as early as you can to grab some unbeatable deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Windsor?

  1. Choose when to go: Check your diary and get packing. Your favourite time of year and the activities on offer will also help you decide when to visit Windsor.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and dining out to flights and activities. Your accommodations will probably be the largest expense during your trip to Windsor.
  3. Decide how long to go away for: Now that you're more familiar with Windsor, you can figure out the ideal length of your break. Create a rough plan and allocate enough time to cover everything you want to see.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find a Windsor vacation package that brings all your bookings together.

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