Windsor Vacations from $449

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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.
Hampton Inn & Suites Albany-Downtown

Hampton Inn & Suites Albany-Downtown

2.5 out of 5
Downtown Albany
Price was $538, price is now $449 per person
$449
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
8.8/10 Excellent! (1,065 reviews)
We had to switch rooms due to a leaking shower. Somehow it was leaking into the room. Additionally the shower was “handicap” accessible but also sprayed water all over the bathroom floor. However they immediately moved us upon complaint.

Reviewed on Apr 20, 2026

Tru By Hilton Albany Crossgates Mall

Tru By Hilton Albany Crossgates Mall

2.5 out of 5
Price was $864, price is now $686 per person
$686
per person
Jun 3 - Jun 8
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
8.6/10 Excellent! (1,006 reviews)
Wonderful service!!! They allowed me to check in early as a courtesy which was very helpful. I love the friendly front desk staff and cleansing of the family friendly hotel. Super convenient location for my daughter's college visit.

Reviewed on Apr 21, 2026

Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was $813, price is now $649 per person
$649
per person
Jun 5 - Jun 8
found 10 hours ago
Roundtrip flight included
Washington (DCA) to Albany (ALB)
8.8/10 Excellent! (1,005 reviews)
Breakfast was good variety

Reviewed on Apr 27, 2026

The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Nothside
Price was $769, price is now $623 per person
$623
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.2/10 Wonderful! (1,004 reviews)
Clean eoom, comfy bed, nice and quiet!

Reviewed on Apr 24, 2026

Best Western Plus Franklin Square Inn Troy/Albany

Best Western Plus Franklin Square Inn Troy/Albany

2.5 out of 5
Price was $659, price is now $557 per person
$557
per person
Jul 2 - Jul 5
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
8.8/10 Excellent! (1,004 reviews)
Parking was safe Had to leave before breakfast

Reviewed on Apr 27, 2026

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Windsor Hotel Deals

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
$142 nightly
The price is $158 total per night from May 19 to May 20
$158 total
May 19 - May 20
Total with taxes and fees
8.8/10 Excellent! (1,005 reviews)
We were happy with the room. Very spacious. The only downside was that the restaurant was closed to regular visitors.

Reviewed on Apr 27, 2026

Hotel Downstreet, an Ascend Collection Hotel
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
$110 nightly
The price is $123 total per night from Apr 29 to Apr 30
$123 total
Apr 29 - Apr 30
Total with taxes and fees
8.8/10 Excellent! (2,342 reviews)
Clean room staff it's respectful and easy going

Reviewed on Apr 28, 2026

Vacation Village in the Berkshires
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $103 total per night from May 4 to May 5
$103 total
May 4 - May 5
Total with taxes and fees
9/10 Wonderful! (920 reviews)
This “hotel” had so much potential, which honestly made the experience more disappointing. It’s described as a boutique hotel, but in reality it’s more of a refurbished motel with a separate building for the restaurant, lounge, and “front desk.” While the photos make it look charming and thoughtfully ...

Reviewed on Apr 27, 2026

Berkshires Untold
See all 1,001 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 $449 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.