Windsor Vacations from $499

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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.
Park Manor Hotel

Park Manor Hotel

4 out of 5
Price was $532, price is now $499 per person
$499
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
7.8/10 Good! (1,196 reviews)
Coffee and muffins for breakfast. Great location first time I stayed in a hotel in my hometown. Bartender Sean on Sunday night was very accommodating. Great bar prices Sunday all day happy hour

Reviewed on Jan 16, 2026

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
Price was $714, price is now $608 per person
$608
per person
Apr 11 - Apr 14
found 10 hours ago
Roundtrip flight included
Charlotte (CLT) to Albany (ALB)
9/10 Wonderful! (781 reviews)
Staff was wonderful. Rooms were very well stocked The kids loved the game room and dvd borrowing

Reviewed on Jan 19, 2026

Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was $597, price is now $537 per person
$537
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
8.8/10 Excellent! (1,001 reviews)
We love this property, we come here twice a year for a mini shopping getaway. Hotel is near 2 walkable restaurants, if you want to have a few drinks you don’t have to drive. Hotel is quite very clean and comfortable. I would recommend it.

Reviewed on Jan 17, 2026

Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
Price was $550, price is now $523 per person
$523
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
8/10 Very Good! (1,214 reviews)
It was a very clean friendly place

Reviewed on Jan 18, 2026

La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area

3 out of 5
Price was $553, price is now $530 per person
$530
per person
Apr 10 - Apr 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
8.8/10 Excellent! (1,042 reviews)
We love the location of the LaQuinta.

Reviewed on Jan 8, 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
$130 nightly
The price is $145 total per night from Feb 1 to Feb 2
$145 total
Feb 1 - Feb 2
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
$177 nightly
The price is $198 total per night from Jan 26 to Jan 27
$198 total
Jan 26 - Jan 27
Total with taxes and fees
9.6/10 Exceptional! (563 reviews)
Everything was excellent

Reviewed on Jan 16, 2026

The Williams Inn
See all 971 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 $499 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.