Windsor Vacations from $498

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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 $580, price is now $498 per person
$498
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
8/10 Very Good! (1,244 reviews)
Rooms were large and very clean. I couldn't figure out the TV, but not a biggie, it was only an overnight stay. Do Not Disturb sign was missing, but easily remedied. Would stay again!

Reviewed on Apr 1, 2026

Hotel Brookmere & Arbor Spa

Hotel Brookmere & Arbor Spa

4 out of 5
Price was $836, price is now $603 per person
$603
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.2/10 Wonderful! (271 reviews)
Located by the elevator was a bit noisy. Other than that, wonderful stay!

Reviewed on Mar 11, 2026

Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
Price was $861, price is now $674 per person
$674
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.8/10 Excellent! (1,013 reviews)
Friendly staff, close to airport, clean

Reviewed on Mar 29, 2026

Hilton Garden Inn Saratoga Springs

Hilton Garden Inn Saratoga Springs

3 out of 5
Price was $799, price is now $628 per person
$628
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
8/10 Very Good! (1,005 reviews)
Bar and restaurant not open on the Dunday I was there

Reviewed on Mar 30, 2026

Hilton Albany

Hilton Albany

3.5 out of 5
Downtown Albany
Price was $736, price is now $617 per person
$617
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
7.2/10 Good! (1,020 reviews)
Very clean and staff was super accommodating

Reviewed on Mar 30, 2026

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Windsor Hotel Deals

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
$131 nightly
The price is $146 total per night from May 3 to May 4
$146 total
May 3 - May 4
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Great location. Within walking distance to MOCA, and a few restaurants that were open during our stay. The town is post industrial and post manufacturing. Walking around MOCA is a wonderful experience in itself as much of the history of the building and surrounding area comes alive and is fascinating.The ...

Reviewed on Mar 22, 2026

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
$108 nightly
The price is $120 total per night from May 3 to May 4
$120 total
May 3 - May 4
Total with taxes and fees
9/10 Wonderful! (892 reviews)
Clean, quiet, spacious, comfortable, and lovely furnishings! It was a very relaxing overnight.

Reviewed on Mar 31, 2026

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $114 total per night from Apr 5 to Apr 6
$114 total
Apr 5 - Apr 6
Total with taxes and fees
9/10 Wonderful! (884 reviews)
Easy check-in, secure and clean

Reviewed on Mar 30, 2026

Berkshires Untold
See all 1,008 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 $498 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.