Windsor Vacations from $505

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.
Bluebird Spa City Motor Lodge

Bluebird Spa City Motor Lodge

3 out of 5
Downtown Saratoga Springs
Price was $597, price is now $505 per person
$505
per person
Dec 23 - Dec 26
found 10 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
18/10 Exceptional! (801 reviews)
Fantastic place to stay

Reviewed on Nov 15, 2025

Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Price was $751, price is now $517 per person
$517
per person
Dec 23 - Dec 26
found 10 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
18.4/10 Exceptional! (218 reviews)
Room spotless. However no cups in bathroom. Wine chiller did not work and had to be replaced. Also had to request clothing hangers for clothing. Only two hangers were in room.

Reviewed on Nov 9, 2025

Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was $1,371, price is now $1,120 per person
$1,120
per person
Dec 23 - Dec 26
found 10 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
18.8/10 Exceptional! (531 reviews)
I’m returning 3d time in this place and will back again .im appreciate peaceful involvement there

Reviewed on Nov 20, 2025

The White House Inn

The White House Inn

3.5 out of 5
Price was $731, price is now $606 per person
$606
per person
Jan 16 - Jan 19
found 16 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
18.4/10 Exceptional! (254 reviews)
The room was beautiful and the historic charm was wonderful

Reviewed on Nov 11, 2025

27 Lincoln

27 Lincoln

2 out of 5
Price was $844, price is now $705 per person
$705
per person
Dec 23 - Dec 26
found 10 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
No reviews
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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 $505 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.

Explore a world of travel with Expedia

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