Windsor Vacations from $406

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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.

The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
The Clocktower Hotel at Century House, an Ascend Collection Hotel

The Clocktower Hotel at Century House, an Ascend Collection Hotel

2.5 out of 5
Price was $499, price is now $406 per person
$406
per person
Feb 19 - Feb 22
found 20 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Albany (ALB)
8.4/10 Very Good! (1,004 reviews)
Everything was great except we stayed 4 nights and never once was our room cleaned or towels refreshed.

Reviewed on Dec 7, 2025

The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Nothside
Price was $649, price is now $441 per person
$441
per person
Feb 19 - Feb 22
found 20 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) 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 Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was $519, price is now $436 per person
$436
per person
Feb 19 - Feb 22
found 20 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Albany (ALB)
8.8/10 Excellent! (1,001 reviews)
Clean room, amenities, staff

Reviewed on Dec 5, 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 19 - Feb 22
found 20 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Albany (ALB)
9.2/10 Wonderful! (1,003 reviews)
Clean room, healthy breakfast options including fresh fruit and berries. Coffee could be so much better. Don’t water the coffee down.

Reviewed on Dec 14, 2025

Home2 Suites by Hilton Albany Wolf Rd

Home2 Suites by Hilton Albany Wolf Rd

3 out of 5
Price was $650, price is now $556 per person
$556
per person
Feb 19 - Feb 22
found 20 hours ago
Roundtrip non-stop flight included
New Orleans (MSY) to Albany (ALB)
8.6/10 Excellent! (609 reviews)
Staff is always nice. I love the rooms. Comfortable, full refrigerator and a table i can pull out and work on anywhere in the room. I try to stay here every time i have to come in for work.

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
$126 nightly
The price is $141 total per night from Dec 15 to Dec 16
$141 total
Dec 15 - Dec 16
Total with taxes and fees
8.6/10 Excellent! (2,169 reviews)
Your staff is very courteous and yes my room was spotless.

Reviewed on Dec 13, 2025

Vacation Village in the Berkshires
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $208 total per night from Dec 15 to Dec 16
$208 total
Dec 15 - Dec 16
Total with taxes and fees
9.6/10 Exceptional! (548 reviews)
Room was very clean. Didn’t have breakfast. Staff was friendly and check in was quick.

Reviewed on Dec 7, 2025

The Williams Inn
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street Pittsfield MA
Fully refundable
$93 nightly
The price is $104 total per night from Dec 17 to Dec 18
$104 total
Dec 17 - Dec 18
Total with taxes and fees
8/10 Very Good! (984 reviews)
Clean and comfortable

Reviewed on Dec 7, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
See all 973 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 $406 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.