Windsor Vacations from $304

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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.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Price was $492, price is now $304 per person
$304
per person
Jan 22 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (2,359 reviews)
Fantastic place to stay! Room was very comfortable and a normal, large size. The complimentary espresso machine, water and mini bar items made the stay extremely welcoming! I will definitely be staying there again. Highly recommended.

Reviewed on Nov 12, 2026

The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Manhattan
Save 100% on your flight
Price was $2,754, price is now $1,583 per person
$1,583
per person
Jan 16 - Jan 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.6/10 Exceptional! (1,006 reviews)

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was $4,402, price is now $2,715 per person
$2,715
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
I found slippers from a previous costumer at my room… they def didn’t clean well! I got allergies and despite the demands for ice they would arrive only a day later

Reviewed on Nov 12, 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was $3,635, price is now $2,246 per person
$2,246
per person
Dec 24 - Dec 31
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
Our servis was excellent. Maria is the best staff, so helpfully and really nice so I could take she with me home 😊

Reviewed on Nov 11, 2026

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Save 100% on your flight
Price was $1,781, price is now $1,103 per person
$1,103
per person
Jan 15 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (293 reviews)
The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong

Reviewed on Nov 6, 2026

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Windsor Hotel Deals

MHO Hotel Bordentown

MHO Hotel Bordentown

2 out of 5
187 US 130 and 206 Bordentown NJ
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $71 total per night from Nov 29 to Nov 30
$71 total
Nov 29 - Nov 30
Total with taxes and fees
MHO Hotel Bordentown
The Heldrich Hotel

The Heldrich Hotel

4 out of 5
10 Livingston Avenue New Brunswick NJ
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $152 total per night from Nov 30 to Dec 1
$152 total
Nov 30 - Dec 1
Total with taxes and fees
The Heldrich Hotel
Hyatt Regency Princeton

Hyatt Regency Princeton

4 out of 5
102 Carnegie Ctr Princeton NJ
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $135 total per night from Nov 19 to Nov 20
$135 total
Nov 19 - Nov 20
Total with taxes and fees
Hyatt Regency Princeton
See all 394 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 $304 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.