Windsor Vacations from $451

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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.
Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was $847, price is now $451 per person
$451
per person
May 27 - May 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (7,024 reviews)
The front desk clerk was helpful and very polite! He made our stay. The room is just that, a room. It was clean and had a nice size bathroom. This hotel was exactly what we needed for a quick trip to see a broadway play. A block away from Times Square, you had all of the amenities that you need..

Reviewed on Mar 11, 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was $3,335, price is now $1,764 per person
$1,764
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,001 reviews)
Excellent stay, very clean spacious rooms. Location is great - close to everything. Only downfall was the bathroom, very tiny with a pedestal sink right next to the toilet, not great for women who need to get ready.

Reviewed on Feb 24, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Price was $4,891, price is now $2,665 per person
$2,665
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (655 reviews)
Close to major shopping and multiple dining options

Reviewed on Jan 21, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was $4,042, price is now $2,244 per person
$2,244
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,003 reviews)
Spotless property and extremely friendly staff! Would definitely stay here again!

Reviewed on Mar 1, 2026

Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,325, price is now $748 per person
$748
per person
May 23 - May 29
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (1,755 reviews)
Not bad acces to Times Square but old building and smelled like smoke in the room.

Reviewed on Mar 11, 2026

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Windsor Hotel Deals

Hilton East Brunswick Hotel & Executive Meeting Center

Hilton East Brunswick Hotel & Executive Meeting Center

3.5 out of 5
3 Tower Center Blvd East Brunswick NJ
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $103 total per night from Mar 29 to Mar 30
$103 total
Mar 29 - Mar 30
Total with taxes and fees
7.4/10 Good! (1,022 reviews)
Friendly staff.

Reviewed on Mar 11, 2026

Hilton East Brunswick Hotel & Executive Meeting Center
Hyatt Regency Princeton

Hyatt Regency Princeton

4 out of 5
102 Carnegie Ctr Princeton NJ
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $151 total per night from Mar 22 to Mar 23
$151 total
Mar 22 - Mar 23
Total with taxes and fees
8.8/10 Excellent! (1,158 reviews)
Everything was great

Reviewed on Mar 11, 2026

Hyatt Regency Princeton
MHO Hotel Bordentown

MHO Hotel Bordentown

2 out of 5
187 US 130 and 206 Bordentown NJ
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $76 total per night from Mar 12 to Mar 13
$76 total
Mar 12 - Mar 13
Total with taxes and fees
8.2/10 Very Good! (1,008 reviews)
Everything was worth it!

Reviewed on Mar 6, 2026

MHO Hotel Bordentown
See all 393 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
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 $451 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?

  1. Pick your travel dates: The things you plan to do in Windsor and your preferred season can help you decide when to go.
  2. 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.
  3. 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.
  4. 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.
  5. Bundle your accommodations and airfare: After you've settled on your travel dates and duration, book the ideal Windsor vacation package for you.
  6. 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.