Windsor Vacations from $443

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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.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $596, price is now $443 per person
$443
per person
Feb 19 - Feb 23
found 14 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
8.8/10 Excellent! (2,134 reviews)
Although the bed was comfortable the room overall needed help. There were cosmetic issues, like pealing paint and cobwebs in the fireplace.

Reviewed on Dec 11, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,089, price is now $721 per person
$721
per person
Feb 13 - Feb 16
found 17 hours ago
Roundtrip flight included
Miami (MIA) to Albany (ALB)
9.4/10 Exceptional! (13 reviews)
Wow, just wow! My high school friend and I met up at Prospect Berkshires for a girls weekend. We had an incredible time relaxing by using all the amenities. The staff are so helpful and profession.

Reviewed on Nov 29, 2025

Gedney Farm

Gedney Farm

3.5 out of 5
Price was $771, price is now $551 per person
$551
per person
Feb 13 - Feb 16
found 17 hours ago
Roundtrip flight included
Miami (MIA) to Albany (ALB)
9.2/10 Wonderful! (132 reviews)
My wife and I chose Gedney Farms at the last minute to enjoy a quick escape from the city. The staff was friendly and welcoming. The checkin and checkout experience was seamless. The room had a truly rustic charm, and clean and orderly. In the morning we took a nice walk on the grounds. For a quick and relaxing getaway, Gedney Farms is a great choice.

Reviewed on Nov 2, 2025

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 $1,541, price is now $1,109 per person
$1,109
per person
Feb 19 - Feb 23
found 14 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
7.4/10 Good! (567 reviews)
Nicely decorated for Christmas. Helpful and attentive staff, Lack of heat in some of the public areas like near the library was an issue, but they tried by keeping the fireplace going. As a helpful hint- the fireplace area in the library was drafty and cold. You can go a long way toward fixing this by repairing or replacing that door that leads outside. There’s a 1 inch gap there. Also, while this is an issue, close those 2 inside doors. That works.

Reviewed on Dec 7, 2025

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $807, price is now $613 per person
$613
per person
Feb 13 - Feb 16
found 17 hours ago
Roundtrip flight included
Miami (MIA) to Albany (ALB)
9/10 Wonderful! (1,002 reviews)
The Inn was very nice and the staff was super friendly and attentive.

Reviewed on Dec 12, 2025

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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
$126 nightly
The price is $141 total per night from Jan 4 to Jan 5
$141 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.6/10 Excellent! (2,169 reviews)
Your staff is very courteous and yes my room was spotless.

Reviewed on Dec 13, 2025

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
$186 nightly
The price is $208 total per night from Dec 21 to Dec 22
$208 total
Dec 21 - Dec 22
Total with taxes and fees
9.6/10 Exceptional! (549 reviews)
Room was very clean. Didn’t have breakfast. Staff was friendly and check in was quick.

Reviewed on Dec 7, 2025

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 refundableReserve now, pay when you stay
$93 nightly
The price is $104 total per night from Dec 24 to Dec 25
$104 total
Dec 24 - Dec 25
Total with taxes and fees
8/10 Very Good! (988 reviews)
Very clean and timely and efficient and the lady who checked me in named Valerie did an amazing job and was very informative and helpful .

Reviewed on Dec 15, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
See all 970 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 $443 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.