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.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
per person
Feb. 8 - Feb. 11
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
7.4/10 Good! (427 reviews)
A good place but it did not meet my exoectations of a resort.

Reviewed on Nov. 27, 2024

South Shire

South Shire

4 out of 5
per person
Feb. 8 - Feb. 15
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (79 reviews)
It’s a very nice inn and staff were amazing

Reviewed on Dec. 15, 2024

The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

3.5 out of 5
per person
Feb. 8 - Feb. 15
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9.4/10 Exceptional! (371 reviews)
The Porches is always a treasure in the midst of chain hotels. Just the right balance of "old school" with contemporary charm. It's the place to stay in North Adams if you can get in!!

Reviewed on Nov. 23, 2024

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
per person
Feb. 8 - Feb. 15
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.6/10 Excellent! (1,750 reviews)
Nice and quiet family get a way

Reviewed on Dec. 16, 2024

The Hotel Vervana at Bennington

The Hotel Vervana at Bennington

2.5 out of 5
per person
Feb. 8 - Feb. 15
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.2/10 Very Good! (1,001 reviews)
Updated and affordable rooms. Walkable to downtown. Lots of parking. Overall a great stay.

Reviewed on Dec. 13, 2024

Ready to book your vacation to Windsor?

 

Choose your dates

Windsor Hotel Deals

Hotel Downstreet
Hotel Downstreet
3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Jan. 12 to Jan. 13
CA $167
CA $187 total
includes taxes & fees
Jan 12 - Jan 13, 2025
8.6/10 Excellent! (1,001 reviews)
"The property is gorgeous and everything is lovely!"

Reviewed on Dec. 27, 2024

Hotel Downstreet
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 CA $128 per night from Jan. 5 to Jan. 6
CA $128
CA $143 total
includes taxes & fees
Jan 5 - Jan 6, 2025
9/10 Wonderful! (458 reviews)
"Really loved the design and comfort. The lobby was exquisite, and the rooms were gorgeous."

Reviewed on Dec. 26, 2024

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 CA $140 per night from Jan. 5 to Jan. 6
CA $140
CA $156 total
includes taxes & fees
Jan 5 - Jan 6, 2025
9/10 Wonderful! (1,001 reviews)
Great stay at the Yankee Inn!
"Very nice stay with friendly and helpful staff. Nice breakfast in the morning. Comfortable room."

Reviewed on Dec. 27, 2024

The Yankee, Trademark Collection by Wyndham
See all 896 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from CA $857 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.