Windsor Vacations from $468

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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 Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Nothside
Price was $554, price is now $468 per person
$468
per person
Feb 27 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)
I also have a nice time at this hotel it's friendly convenient and clean I wish they had more food choices and more things to do but always nice to stay here. I'm exited for my next trip.

Reviewed on Jan 13, 2026

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Manchester Village Historic District
Save 100% on your flight
Price was $1,205, price is now $850 per person
$850
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
7.4/10 Good! (567 reviews)
The resort really needs updating....

Reviewed on Jan 14, 2026

The Manchester View

The Manchester View

2.5 out of 5
Price was $719, price is now $556 per person
$556
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
9.4/10 Exceptional! (772 reviews)
Safe, clean and spacious. Very cute, good Mountain View’s out the back door. Very good coffee cake at breakfast

Reviewed on Jan 20, 2026

Hilton Albany

Hilton Albany

3.5 out of 5
Downtown Albany
Price was $756, price is now $639 per person
$639
per person
Feb 27 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
7/10 Good! (1,002 reviews)
It wasn’t stellar, but it was a good hotel. The room was modern. I couldn’t figure out the TV. I had to watch through my own account so I don’t think there was any TV included with the room, but the bed was clean and comfortable housekeeping was good. Front desk was good. Everyone was good.

Reviewed on Jan 16, 2026

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

3 out of 5
Price was $685, price is now $587 per person
$587
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
8.4/10 Very Good! (855 reviews)
Usually not a “motel” person, but this was a surprise… very spacious and clean. The decor is dated, but amenities are convenient. Staff was friendly.

Reviewed on Jan 18, 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 Jan 25 to Jan 26
$141 total
Jan 25 - Jan 26
Total with taxes and fees
8.6/10 Excellent! (2,208 reviews)
It is one of my favorite places to go but sometimes it is overcrowded and the people can be rude and rowdy. But the staff is fantastic they do a great job even with the crowds.

Reviewed on Jan 16, 2026

Vacation Village in the Berkshires
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 Feb 18 to Feb 19
$136 total
Feb 18 - Feb 19
Total with taxes and fees
9/10 Wonderful! (812 reviews)
Wonderful night!! Staff go out of their way to help you!!

Reviewed on Jan 17, 2026

Berkshire Mountain Lodge
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 Jan 25 to Jan 26
$208 total
Jan 25 - Jan 26
Total with taxes and fees
9.6/10 Exceptional! (563 reviews)
Everything was excellent

Reviewed on Jan 16, 2026

The Williams Inn
See all 959 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 $468 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.