Windsor Vacations from $292

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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 Wiltwyck

The Wiltwyck

3.5 out of 5
Price was $365, price is now $292 per person
$292
per person
Feb 26 - Mar 1
found 11 hours ago
Roundtrip flight included
Charlotte (CLT) to Albany (ALB)
9.4/10 Exceptional! (162 reviews)
Great stay! Well decorated and a beautiful building walking distance from shops restos and the beautiful downtown. The host was waiting to greet us even though we were quite late to check in. Would stay again!

Reviewed on Dec 30, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Manchester Village Historic District
Price was $989, price is now $750 per person
$750
per person
Feb 27 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
7.4/10 Good! (567 reviews)
The resort really needs updating....

Reviewed on Jan 14, 2026

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

3 out of 5
Save 100% on your flight
Price was $967, price is now $755 per person
$755
per person
Apr 6 - Apr 10
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
No reviews
Luxury Private Estate w Pool Near Rhinebeck

Luxury Private Estate w Pool Near Rhinebeck

2 out of 5
Save 100% on your flight
Price was $2,434, price is now $1,949 per person
$1,949
per person
Apr 6 - Apr 10
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
No reviews
Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was $1,627, price is now $1,317 per person
$1,317
per person
Feb 26 - Mar 1
found 5 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Albany (ALB)
9.4/10 Exceptional! (531 reviews)
It was a pleasant stay, very little staff attention

Reviewed on Jan 7, 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 19 to Jan 20
$141 total
Jan 19 - Jan 20
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
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $206 total per night from Jan 27 to Jan 28
$206 total
Jan 27 - Jan 28
Total with taxes and fees
9.6/10 Exceptional! (560 reviews)
General ambience is lovely.

Reviewed on Jan 8, 2026

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
$98 nightly
The price is $109 total per night from Jan 23 to Jan 24
$109 total
Jan 23 - Jan 24
Total with taxes and fees
8/10 Very Good! (1,004 reviews)
Another good 2 night stay. Did have a slow shower drain but reported that to maintenance and it was fixed right away. Good service. And also the restaurant is quite good featuring an American menu with a Southern emphasis. The parking garage demo is moving quickly by the way. More parking close to ...

Reviewed on Jan 7, 2026

Holiday Inn & Suites Pittsfield-Berkshires by IHG
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 $292 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.