Windsor Vacations from $707

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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.
Country Inn & Suites by Radisson, Downtown Albany New York

Country Inn & Suites by Radisson, Downtown Albany New York

3 out of 5
Downtown Albany
Price was $865, price is now $707 per person
$707
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
8/10 Very Good! (644 reviews)
Was perfect for the price. Recommended.

Reviewed on May 29, 2026

Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was $1,267, price is now $961 per person
$961
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
8.8/10 Excellent! (1,015 reviews)
Very convenient to the airport. Nice staff. Didn’t have breakfast there so I can’t say

Reviewed on May 27, 2026

La Quinta Inn & Suites by Wyndham Latham Albany Airport

La Quinta Inn & Suites by Wyndham Latham Albany Airport

3 out of 5
Price was $1,020, price is now $846 per person
$846
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
7.2/10 Good! (1,003 reviews)
Room was cleaned daily. Staff was friendly and talkative. AC\Heat work fine. Shampoo, conditioner and soap pump in the shower. Breakfast consisted of home made waffles, eggs, potatoes, 3 cereals, oatmeal, yogurt, coffee, juice, bagels, bread good sort of condiments. Breakfast hours: 6-9 M-F. 7-10 S-S. Landscape and parameter could use some TLC for cleaning. Nice small pool. Exercise equipment. Small food choices if you need a quick snack. I would stay here again. Quite area. Only real downside is the construction next door starts at 7am 😩. Give it a stay.

Reviewed on May 29, 2026

Hilton Albany

Hilton Albany

3.5 out of 5
Downtown Albany
Price was $972, price is now $812 per person
$812
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
7.2/10 Good! (1,005 reviews)
The front desk staff was very nice and helpful. The hotel is very nice and clean. There was a ton of kids there for a basketball tournament and they were all very well behaved and not running around making a lot of noise. My room was nice except for the toilet in my room. It was very low like it was meant for a child. And the shower I felt like I was going to fall. That made me very nervous. Went downstairs for breakfast and that was good. I didn't like the fact that I had to pay for parking but other than that I had a good stay.

Reviewed on May 25, 2026

Gorgeous Hudson Valley Farmhouse On 14 Acres 3 Bedroom Home

Gorgeous Hudson Valley Farmhouse On 14 Acres 3 Bedroom Home

3.5 out of 5
Price was $2,102, price is now $1,758 per person
$1,758
per person
Jul 16 - Jul 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
No reviews
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Windsor Hotel Deals

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 May 31 to Jun 1
$145 total
May 31 - Jun 1
Total with taxes and fees
9/10 Wonderful! (960 reviews)
"Hot tub doesn’t go above 95 which is colder than you think, didn’t have any luggage carts available after asking 3 different people, but it’s a charming place to end on a positive note"

Reviewed on May 28, 2026

Berkshire Mountain Lodge
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
$128 nightly
The price is $143 total per night from May 31 to Jun 1
$143 total
May 31 - Jun 1
Total with taxes and fees
8.8/10 Excellent! (2,378 reviews)
"Beautiful property in the middle of the mountains"

Reviewed on May 28, 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
$154 nightly
The price is $172 total per night from Jun 1 to Jun 2
$172 total
Jun 1 - Jun 2
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
"Room was newly completed and fresh."

Reviewed on May 25, 2026

Hotel Downstreet, an Ascend Collection Hotel
See all 989 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 $707 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.