Windsor Vacations from $694

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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 Beacon

Hotel Beacon

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,177, price is now $694 per person
$694
per person
Sep 9 - Sep 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.4/10 Exceptional! (1,496 reviews)
Great location. Staff was great but unfortunately no restaurant or bar like Expedia said.

Reviewed on Jun 18, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was $2,841, price is now $1,557 per person
$1,557
per person
Aug 2 - Aug 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9/10 Wonderful! (1,000 reviews)
Excellent and well kept hotel. Friendly and helpful staff. Awesome location.

Reviewed on Jun 6, 2026

Hilton Garden Inn New York/Manhattan-Midtown East

Hilton Garden Inn New York/Manhattan-Midtown East

3.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,346, price is now $759 per person
$759
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Newark Liberty Intl. Airport (EWR)
7.8/10 Good! (1,761 reviews)
Elevators could use some work.

Reviewed on Jun 23, 2026

Mandarin Oriental, New York

Mandarin Oriental, New York

5 out of 5
Manhattan
Save 100% on your flight
Price was $5,997, price is now $3,522 per person
$3,522
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.2/10 Wonderful! (645 reviews)
Amazing hotel, staff make the whole experience, bar is great. Reception and concierge team are excellent, in particular Lauren who made check in a breeze. Gym and pool are excellent for a New York hotel.

Reviewed on Jun 21, 2026

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Save 100% on your flight
Price was $1,351, price is now $805 per person
$805
per person
Aug 25 - Aug 30
found 1 day ago
Roundtrip flight included
Dallas (DAL) to New York (JFK)
8.8/10 Excellent! (7,502 reviews)
Hotel was quaint and charming! The beds were comfortable and clean. Staff was super helpful and even let us borrow an umbrella and were really quick with food recommendations and subway directions! Loved our stay…would stay here again.

Reviewed on Jun 23, 2026

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Windsor Hotel Deals

Hyatt Regency Princeton

Hyatt Regency Princeton

4 out of 5
102 Carnegie Ctr Princeton NJ
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $165 total per night from Jul 24 to Jul 25
$165 total
Jul 24 - Jul 25
Total with taxes and fees
8.8/10 Excellent! (1,310 reviews)
"This was my 2nd time staying at the Hyatt Regency in Princeton, NJ. We stayed there last year as well during a college tour. No hassle check in, clean room, and reasonable cost. The overall energy was just positive. On site breakfast buffet was delicious, and service was perfect."

Reviewed on Jun 21, 2026

Hyatt Regency Princeton
The Westin Princeton at Forrestal Village

The Westin Princeton at Forrestal Village

4 out of 5
201 Village Blvd Princeton NJ
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $174 total per night from Jul 12 to Jul 13
$174 total
Jul 12 - Jul 13
Total with taxes and fees
8.8/10 Excellent! (1,005 reviews)
"Stay was comfortable, only complaint is that housekeeping wouldn’t come to clean until later in day. One day I we were out from 9am-4:30pm and housekeeping had just gotten to the room. Another day was a similar experience where we were gone from 10am-2pm and no housekeeping. Also had to request bedding ..."

Reviewed on Jun 15, 2026

The Westin Princeton at Forrestal Village
Crowne Plaza Princeton-Conference Center by IHG

Crowne Plaza Princeton-Conference Center by IHG

3.5 out of 5
900 Scudders Mill Road Plainsboro NJ
$118 nightly
The price is $135 total per night from Jul 23 to Jul 24
$135 total
Jul 23 - Jul 24
Total with taxes and fees
8.6/10 Excellent! (1,018 reviews)
"Breakfast staff particularly friendly and helpful. A big problem for us: no luggage carts were available, either in the evening when we checked in, or the morning when we checked out. The front desk staff were not helpful. When we checked in we were told that “all six carts were upstairs somewhere,” ..."

Reviewed on Jun 23, 2026

Crowne Plaza Princeton-Conference Center by IHG
See all 433 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 $694 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.