Windsor Vacations from $465

Book a Hotel + Flight or Car together to unlock savings

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.
Lodges At Cresthaven

Lodges At Cresthaven

4 out of 5
Price was $579, price is now $465 per person
$465
per person
Dec 5 - Dec 8
found 20 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.4/10 Exceptional! (508 reviews)
Beautiful views, spotless room and the staff in the office were very friendly! Great communication and seamless check in after hours! We've stayed many times prior to this visit and will be back again!

Reviewed on Nov 4, 2025

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Save 100% on your flight
Price was $796, price is now $548 per person
$548
per person
Dec 30 - Jan 2
found 16 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
No reviews
Lovely room and great products in the room. Really enjoyed the kind staff and the relaxing vibes.

Reviewed on Nov 3, 2025

Church Des Artistes Guest House

Church Des Artistes Guest House

3 out of 5
Roundout
Save 100% on your flight
Price was $3,292, price is now $2,437 per person
$2,437
per person
Dec 30 - Jan 2
found 16 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
9.4/10 Exceptional! (18 reviews)
The White House Inn

The White House Inn

3.5 out of 5
Price was $1,205, price is now $908 per person
$908
per person
Dec 19 - Dec 26
found 1 hour ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
9.2/10 Wonderful! (238 reviews)
The property is beautiful. The room was clean and comfortable.

Reviewed on Nov 3, 2025

Urban Cowboy Lodge

Urban Cowboy Lodge

5 out of 5
Save 100% on your flight
Price was $1,196, price is now $952 per person
$952
per person
Dec 30 - Jan 2
found 16 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
9.2/10 Wonderful! (168 reviews)
The room was very clean and well maintained. The staff from the desk to the restaurant were extremely polite and helpful. The location of the hotel is very peaceful and isolated, no cell service, no tv in room, nothing outside but beautiful nature and bright stars at night. The perfect spot to get away from the city life without going too far with your significant other.

Reviewed on Oct 29, 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
$112 nightly
The price is $125 total per night from Nov 12 to Nov 13
$125 total
Nov 12 - Nov 13
Total with taxes and fees
8.6/10 Excellent! (2,117 reviews)
The amenities are great. The pool and hot tub are very comfortable temperatures, pool tables, ping pong, foosball, arcade games, movie theater, and more.

Reviewed on Nov 2, 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
$150 nightly
The price is $167 total per night from Nov 16 to Nov 17
$167 total
Nov 16 - Nov 17
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
Kind staff!

Reviewed on Oct 28, 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
$113 nightly
The price is $126 total per night from Nov 6 to Nov 7
$126 total
Nov 6 - Nov 7
Total with taxes and fees
9/10 Wonderful! (745 reviews)
Clean, convenience, great staff, quiet, beautiful and secluded yet close to everything! Thank you

Reviewed on Nov 2, 2025

Berkshire Mountain Lodge
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 $465 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.