Windsor Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.

Windsor Hotel Deals

Eden Resort and Suites, BW Premier Collection

Eden Resort and Suites, BW Premier Collection

3.5 out of 5
222 Eden Road Lancaster PA
Fully refundableReserve now, pay when you stay
$153 nightly
The price is $170 total per night from May 31 to Jun 1
$170 total
May 31 - Jun 1
Total with taxes and fees
9/10 Wonderful! (1,017 reviews)
The resort and room were very clean. Checking in and checking out was seamless. The pool was nice and overall property amenities were great. The area is perfect as there are many dinning and shopping options around the resort. A gas station feet’s away from the resort. Overall great and convenient ...

Reviewed on May 6, 2026

Eden Resort and Suites, BW Premier Collection
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
$75 nightly
The price is $83 total per night from May 21 to May 22
$83 total
May 21 - May 22
Total with taxes and fees
7.8/10 Good! (1,195 reviews)
Staff members are very friendly and helpful. Check-in was fast, efficient and the fastest of any hotel where I have stayed. The hotel was very quiet and the bed was comfortable. Breakfast was good, with a variety of choices. The hotel provided a list of nearby restaurants and activities. It is an ...

Reviewed on May 4, 2026

Days Inn & Suites by Wyndham Lancaster Amish Country
Lancaster Arts Hotel

Lancaster Arts Hotel

3.5 out of 5
300 Harrisburg Ave Lancaster PA
Fully refundableReserve now, pay when you stay
$148 nightly
The price is $164 total per night from May 31 to Jun 1
$164 total
May 31 - Jun 1
Total with taxes and fees
9.4/10 Exceptional! (1,013 reviews)
Great location and historical setting.

Reviewed on May 6, 2026

Lancaster Arts Hotel
See all 515 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
Closest Airport
Harrisburg Intl. Airport (MDT)
Population
1,500
Top Sights
Moon Dancer Winery, Susquehannock State Park and York Little Theatre

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Windsor vacation package cost?
Offering excellent value package deals 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.