Windsor Vacations from $662

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Your Windsor Vacation

Book a Windsor vacation package and get set to experience this captivating city the stress-free way. Think about staying in the neighborhood of East York, which is great for shopping and history. Heritage Hill Golf Course, AvalancheXpress and Samuel S. Lewis State Park are just a few of the attractions worth visiting during your trip to Windsor. Whoever you're heading away with and whatever you want to spend, your dream Windsor vacation is just a few clicks away with Expedia.

The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Susquehanna Manor Inn

Susquehanna Manor Inn

3 out of 5
Price was $687, price is now $662 per person
$662
per person
Oct 8 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Lancaster (LNS)
9.4/10 Exceptional! (99 reviews)
Beautiful property and amazing host. The porch is worth the credit. The decor perfectly matches the outdoors. Everything feels authentic and like it fits and belongs.. This cozy B&B is a diamond in the rough

Reviewed on Jul 18, 2025

Annville Inn Bed and Breakfast

Annville Inn Bed and Breakfast

3.5 out of 5
Price was $963, price is now $958 per person
$958
per person
Oct 8 - Oct 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Lancaster (LNS)
9.4/10 Exceptional! (321 reviews)
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Windsor Hotel Deals

Lancaster Marriott at Penn Square

Lancaster Marriott at Penn Square

3.5 out of 5
25 South Queen Street, Lancaster, PA
$170 nightly
The price is $189 total per night from Sep 14 to Sep 15
$189 total
Sep 14 - Sep 15
Total with taxes and fees
Lancaster Marriott at Penn Square
Days Inn & Suites by Wyndham Lancaster Amish Country

Days Inn & Suites by Wyndham Lancaster Amish Country

2.5 out of 5
2929 Hempland Rd, Lancaster, PA
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $79 total per night from Sep 7 to Sep 8
$79 total
Sep 7 - Sep 8
Total with taxes and fees
Days Inn & Suites by Wyndham Lancaster Amish Country
Heritage Hotel Lancaster

Heritage Hotel Lancaster

3 out of 5
500 Centerville Rd, Lancaster, PA
$127 nightly
The price is $140 total per night from Sep 14 to Sep 15
$140 total
Sep 14 - Sep 15
Total with taxes and fees
Heritage Hotel Lancaster
See all 459 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.

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Frequently asked questions

How much does a Windsor vacation package cost?
Offering excellent value package deals from $662 on Expedia, you'll be surprised at how little a vacation to Windsor costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Windsor?
November, December and January are great times to look for cheap Windsor vacation packages. Opting to travel in quieter periods means you can typically find better prices on flights and accommodations.
How many days is enough for Windsor?
The ideal duration for your Windsor vacation depends on what you'd like to see. Usually, a few days to a week will give you enough time to check out all the top sights and explore some hidden treasures along the way.
How to find the best Windsor package deals?
Start your search for a Windsor package deal by entering your destination and travel dates under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Windsor package deal straight away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Windsor escape underway.
Is it cheaper to book a Windsor vacation as a package?
You can enjoy significant savings on your next Windsor break by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to see some great hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Windsor?
Score amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Windsor getaway.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
Secure your dream escape to Windsor with help from Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait for the next payday — we've joined forces with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to budget for your trip and snag great deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.