Windsor Vacations from $485

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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 Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was $531, price is now $485 per person
$485
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Myrtle Beach (MYR) to Albany (ALB)
8.8/10 Excellent! (1,001 reviews)
stay was great. hotel is very clean.

Reviewed on Jan 30, 2026

The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Nothside
Price was $665, price is now $589 per person
$589
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Myrtle Beach (MYR) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)
The rooms were very nice. The hotel overall was quiet and clean

Reviewed on Jan 27, 2026

Hilton Albany

Hilton Albany

3.5 out of 5
Downtown Albany
Price was $630, price is now $573 per person
$573
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Myrtle Beach (MYR) to Albany (ALB)
7/10 Good! (1,002 reviews)
Great room. Extremely courteous staff.

Reviewed on Jan 31, 2026

Marriott Albany

Marriott Albany

3.5 out of 5
Price was $662, price is now $607 per person
$607
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Myrtle Beach (MYR) to Albany (ALB)
8.2/10 Very Good! (751 reviews)
The staff were super nice and patient. The beds were comfortable and the sheets were great. Large Gum as well.

Reviewed on Jan 26, 2026

Hampton Inn Clifton Park

Hampton Inn Clifton Park

2.5 out of 5
Price was $645, price is now $604 per person
$604
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip non-stop flight included
Myrtle Beach (MYR) to Albany (ALB)
9.2/10 Wonderful! (1,002 reviews)
The room was very clean. The staff at the main desk were warm and welcoming. The free breakfast options were good and plentiful. The coffee was just average. Overall, we enjoyed ourselves and would return, if the occasion called for it.

Reviewed on Jan 30, 2026

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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
$126 nightly
The price is $141 total per night from Feb 22 to Feb 23
$141 total
Feb 22 - Feb 23
Total with taxes and fees
8.6/10 Excellent! (2,219 reviews)
Everything was great, the staff, the room, and the amenities. We will be coming back.

Reviewed on Jan 25, 2026

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
$126 nightly
The price is $141 total per night from Feb 24 to Feb 25
$141 total
Feb 24 - Feb 25
Total with taxes and fees
8.8/10 Excellent! (1,005 reviews)
Nice location and beautiful lobby.

Reviewed on Jan 27, 2026

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
$121 nightly
The price is $136 total per night from Mar 2 to Mar 3
$136 total
Mar 2 - Mar 3
Total with taxes and fees
9/10 Wonderful! (821 reviews)
Friendly informed staff, super clean room, the hot chocolate machine !!!!!

Reviewed on Jan 27, 2026

Berkshire Mountain Lodge
See all 981 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 $485 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.