Windsor Vacations from $396

Book a Hotel + Flight or Car together to unlock savings

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.

The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Clifton Park

Hampton Inn Clifton Park

2.5 out of 5
Price was $474, price is now $396 per person
$396
per person
Feb 28 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Albany (ALB)
9.2/10 Wonderful! (1,002 reviews)
It was just as we wanted

Reviewed on Dec 4, 2025

The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Stockade Historic District
Price was $591, price is now $444 per person
$444
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)
Everything about our stay was perfect! The lady at check-in was super friendly, the room was extremely clean and modern. Definitely recommend The Landing!

Reviewed on Nov 23, 2025

Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

2.5 out of 5
Downtown Albany
Price was $779, price is now $651 per person
$651
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Albany (ALB)
8.8/10 Excellent! (1,023 reviews)
everything was great

Reviewed on Dec 6, 2025

Hilton Garden Inn Albany Medical Center

Hilton Garden Inn Albany Medical Center

3 out of 5
Price was $717, price is now $605 per person
$605
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Albany (ALB)
8.6/10 Excellent! (1,002 reviews)
The room could have been in better condition.

Reviewed on Nov 4, 2025

Homewood Suites by Hilton Albany

Homewood Suites by Hilton Albany

3 out of 5
Price was $658, price is now $561 per person
$561
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Albany (ALB)
9.2/10 Wonderful! (1,003 reviews)
Really nice hotel. Great breakfast buffet. Very clean.

Reviewed on Dec 7, 2025

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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
$111 nightly
The price is $124 total per night from Dec 8 to Dec 9
$124 total
Dec 8 - Dec 9
Total with taxes and fees
8.6/10 Excellent! (2,155 reviews)
Great views

Reviewed on Nov 30, 2025

Vacation Village in the Berkshires
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
$107 nightly
The price is $120 total per night from Dec 20 to Dec 21
$120 total
Dec 20 - Dec 21
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Perfect

Reviewed on Dec 1, 2025

Hotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $120 total per night from Jan 6 to Jan 7
$120 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
9/10 Wonderful! (777 reviews)
I am a cross country traveling nurse. The Berkshire Mountain Lodge was perfect for my needs. A fully functioning well appointed kitchen. Spacious living quarters with excellent views. The best water pressure on a shower that I have ever known. Fantastic after a long day of work or out hiking the ...

Reviewed on Dec 4, 2025

Berkshire Mountain Lodge
See all 974 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.

Find the Best Windsor Vacation Packages

Windsor Essential Information

Language
English
Currency
U.S dollars
Population
890
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Colonial Theater, Barrington Stage Company and Berkshire Museum

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Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from $396 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?
October, November and December are the best times to look for cheap Windsor vacation packages. Opting to travel in quieter months means you'll typically find lower prices on flights and accommodations.
How many days is enough for Windsor?
With a well-planned schedule, you can easily hit the main Windsor attractions in a few days. But if you prefer to explore off the beaten track or go on day tours, think about booking your Windsor vacation for longer.
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.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
Your Windsor trip is meant to be a relaxing escape from your daily routine, not a source of money worries. So to give you a bit more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

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