Windsor Vacation Packages
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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.
Top Windsor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area
Price was CA $1,638, price is now CA $1,487 per person
CA $1,487
per person
Sep 15 - Sep 19
found 17 hours ago
Roundtrip flight included
Grande Prairie (YQU) to Albany (ALB)
8.6/10 Excellent! (1,129 reviews)
just average been in nicer la quintas
Reviewed on Jun 20, 2026
Bluebird Spa City Motor Lodge
Downtown Saratoga Springs
Price was CA $2,048, price is now CA $1,740 per person
CA $1,740
per person
Sep 15 - Sep 19
found 17 hours ago
Roundtrip flight included
Grande Prairie (YQU) to Albany (ALB)
9/10 Wonderful! (920 reviews)
This is a hidden gem. The location is right in the heart of town, so convenient to everything. They also have great spaces to enjoy your down time. The patio with fire pit overlooking Broadway was amazing. Top it with friendly attentive staff and your set. We will be back.
Reviewed on Jun 18, 2026
Fairfield Inn & Suites by Marriott Albany Downtown
Downtown Albany
Price was CA $2,119, price is now CA $1,861 per person
CA $1,861
per person
Sep 15 - Sep 19
found 17 hours ago
Roundtrip flight included
Grande Prairie (YQU) to Albany (ALB)
8.6/10 Excellent! (1,006 reviews)
The room was spacious, quiet, and comfortable. The water pressure in the shower was nice. The breakfast was delicious with options including biscuits, fried eggs, shredded cheese, waffles, oatmeal, cereal, pastries, bagels, etc. I found a free parking spot (on Saturday night) in front of the hotel. But my husband had to park his car a good distance away. FYI- the parking garage does not have EV chargers.
Reviewed on Jun 12, 2026
Hampton Inn Albany-Wolf Road (Airport)
Price was CA $1,721, price is now CA $1,535 per person
CA $1,535
per person
Sep 15 - Sep 19
found 17 hours ago
Roundtrip flight included
Grande Prairie (YQU) to Albany (ALB)
8.8/10 Excellent! (1,023 reviews)
Location, decent breakfast and staff was friendly
Reviewed on Jun 21, 2026
Windsor Hotel Deals
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
The price is CA $219 per night from Jun 30 to Jul 1
CA $219
CA $245 total
Jun 30 - Jul 1
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"No real breakfast"
Reviewed on Jun 21, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from Jul 7 to Jul 8
CA $204
CA $228 total
Jul 7 - Jul 8
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"I had an excellent experience with the Yankee Inn. The room was updated and the house keeping was excellent. The location was good and the staff was very nice. The breakfast was very good. I would definitely recommend staying here."
Reviewed on Jun 23, 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from Jun 29 to Jun 30
CA $187
CA $225 total
Jun 29 - Jun 30
includes taxes & fees
8.8/10 Excellent! (2,409 reviews)
"The room was great. Had everything I needed and was very comfortable."
Reviewed on Jun 24, 2026
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.
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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.
