Windsor Vacations from $365

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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
Stockade Historic District
Price was $467, price is now $365 per person
$365
per person
Jan 22 - Jan 25
found 2 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.2/10 Wonderful! (1,006 reviews)
Liked the view from my windows and the room service breakfast was wonderful

Reviewed on Nov 12, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Save 100% on your flight
Price was $1,616, price is now $1,175 per person
$1,175
per person
Dec 26 - Dec 30
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
7.4/10 Good! (549 reviews)
Nice room, comfortable bed. This is an old grand hotel in tip top shape. We often stay in this type of hotel in NH and VT and found the Equinox to be the best maintained of them all. All the architectural class of its age in virtually new condition. Nice, reasonably priced onsite dining. We didn’t use the large indoor pool but it looked first class. Pleasant staff. We hope to return. Recommend “Ok for breakfast”, a 2nd floor breakfast & lunch restaurant downtown.

Reviewed on Oct 27, 2025

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Save 100% on your flight
Price was $1,034, price is now $757 per person
$757
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
9/10 Wonderful! (1,005 reviews)
Absolutely love it Staff is lobbing, attentive and respectful They gave us directions for a beautiful restaurant where we had excellent service Zinc Bistro, which I totally recommend now Beautiful rooms, special, wonderful well done breakfast (as one expects from a real B&B) Perfection.

Reviewed on Nov 11, 2025

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was $948, price is now $720 per person
$720
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
8.6/10 Excellent! (2,062 reviews)
Best of the Berkshires! Clean, Comfortable and convenient. Parking is a bit weird and cramped but not overshadowing the room itself.

Reviewed on Nov 10, 2025

Best Western Plus Franklin Square Inn Troy/Albany

Best Western Plus Franklin Square Inn Troy/Albany

2.5 out of 5
Price was $467, price is now $377 per person
$377
per person
Jan 15 - Jan 18
found 13 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.8/10 Excellent! (1,006 reviews)
Not enough parking spaces

Reviewed on Nov 11, 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
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $133 total per night from Nov 14 to Nov 15
$133 total
Nov 14 - Nov 15
Total with taxes and fees
8.6/10 Excellent! (2,131 reviews)
Good

Reviewed on Nov 10, 2025

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
$144 nightly
The price is $161 total per night from Dec 11 to Dec 12
$161 total
Dec 11 - Dec 12
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
Very clean and inviting Hotel located in downtown area. Very walkable area. Parking was free. Front desk very friendly and helpful. Would stay again.

Reviewed on Nov 3, 2025

Hotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $135 total per night from Nov 13 to Nov 14
$135 total
Nov 13 - Nov 14
Total with taxes and fees
9/10 Wonderful! (750 reviews)
Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome.

Reviewed on Nov 4, 2025

Berkshire Mountain Lodge
See all 984 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 $365 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.