Windsor Vacations from $874
Book a Hotel + Flight or Car together to unlock savings
Your Windsor Vacation
When you book a vacation package to Windsor, you can relax and enjoy your getaway knowing that all your travel arrangements are under control. Discover the many delights of this vibrant city from your base in a neighborhood like Princeton Meadows, which is great for golfing. During your trip to Windsor, carve some time in your schedule for sightseeing. A popular place to begin exploring is Working Dog Winery. Whoever you're escaping with and whatever you plan 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.
Seven Beach Lane
$1,127
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
9.4/10 Exceptional! (29 reviews)
Property was extremely conveniently located to Main Street. The pool was clean with plenty of towels. Staff was pleasant. Great overall experience.
Reviewed on Aug 11, 2026
Cozy Home near City Center with Hot tub
South Philadelphia
$2,507
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Philadelphia (PHL)
10/10 Exceptional! (3 reviews)
This was the perfect place for my group and our needs. Enough beds with options; a dark, quiet room in the basement, a shared room with a two full beds, the top floor king size suite, even a pull out sofa! All useful accommodations for a party of 5 or more. To top it off, the roof top hot tub with a city skyline view was incredible! It was a great location too, in walking distance to our venue in South Philly. Everything worked out perfectly, and I'm grateful that this option was available. Thank you!
Reviewed on Mar 2, 2026
Windsor Hotel Deals
Hyatt Regency Princeton
102 Carnegie Ctr Princeton NJ
Fully refundableReserve now, pay when you stay
$118 nightly
$135 total
Sep 7 - Sep 8
Total with taxes and fees
Hilton East Brunswick Hotel & Executive Meeting Center
3 Tower Center Blvd East Brunswick NJ
Fully refundableReserve now, pay when you stay
$110 nightly
$126 total
Aug 16 - Aug 17
Total with taxes and fees
7.4/10 Good! (1,227 reviews)
"Nice bed with pillows. Huge hotel mostly for trade shows and meetings."
Reviewed on Aug 13, 2026
Holiday Inn East Windsor - Cranbury Area by IHG
399 Monmouth St Hightstown NJ
Fully refundable
$95 nightly
$109 total
Sep 13 - Sep 14
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
"Everything was clean and neat, room looked as it did in the pictures."
Reviewed on Aug 12, 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.
Find the Best Windsor Vacation Packages
Windsor Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Mercer Airport (TTN) |
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Frequently asked questions
How much does a Windsor vacation package cost?
You can snap up a vacation package to this top destination from $874 on Expedia. But how much your vacation to Windsor costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Windsor?
If you're looking to snag a cheap Windsor vacation package, consider traveling in August, September and October. You'll typically find lower rates on hotels and airfares during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Windsor?
With a well-planned itinerary, you can easily tick off the top Windsor attractions in a handful of days. But if you prefer to venture off the beaten track or take day trips, consider booking your Windsor vacation for longer.
How to find the best Windsor package deals?
Start your search for a Windsor package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Windsor package deal straight away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Windsor adventure off to a flying start.
Is it cheaper to book a Windsor vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and hotels separately. Better still, you can personalize your Windsor escape to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Windsor?
If you have your Windsor travel dates locked in, book as early as you can to snap up some outstanding deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Windsor?
- Pick your travel dates: The things you plan to do in Windsor and your preferred season can help you decide when to go.
- Budget wisely: Besides the price of your accommodations, you should factor in other expenses. These include flights, transportation and food. Also, set aside a little extra for unexpected expenses that could arise during your trip to Windsor.
- Use our trip planning tool to discover Windsor: Research every part of your trip to Windsor with this handy planner. Invite family or friends to collaborate on a group getaway, search for hotels or things to do and make bookings.
- Determine how many days away: Start by listing all the attractions you'd like to get to in Windsor. Then, estimate how long you'll need at each, along with any travel time.
- Bundle your accommodations and airfare: After you've settled on your travel dates and duration, book the ideal Windsor vacation package for you.
- Add on excursions and experiences: Read our dedicated travel guide to find some awesome things to do in Windsor. Book tickets or make reservations before you go to save time and skip the hassle of searching for activities once you arrive.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
Your Windsor getaway is meant to be an escape from your busy life, not a source of money-related stress. So to give you more flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.