Windsor Vacations from $370

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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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $717, price is now $370 per person
$370
per person
Nov 4 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,008 reviews)
It was a wonderful stay. We had a girl’s weekend planned and chose to stay here and we were so glad we did. The staff was extremely helpful and friendly and the complimentary breakfast was the best I’ve ever had - everything was so well seasoned. The property is also really lovely - the pool area felt like a little oasis and well maintained. We are planning on coming back again for our next meet up!

Reviewed on Sep 23, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was $1,851, price is now $925 per person
$925
per person
Dec 5 - Dec 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,306 reviews)
Clean comfortable bed

Reviewed on Sep 27, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was $1,682, price is now $857 per person
$857
per person
Nov 4 - Nov 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.8/10 Exceptional! (1,344 reviews)
Great location, modern conveniences, and excellent staff

Reviewed on Sep 27, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $3,298, price is now $1,719 per person
$1,719
per person
Dec 11 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
My husband and I booked a staycation at the hotel (we live in Brooklyn) for our anniversary. We were first given a room facing a wall so we asked for a different room. They gave us one for almost 200 more with a view of the statue of liberty. Went up to room, they didnt change the keys, so they didnt work. Had to go back and get them reactivated. Nice view, room was fine. That said it was SO LOUD. 8th floor under the "club" is a nightmare. The noise/base was going through 3am. I couldnt sleep so we decided to check out the next day and asked for a refund. The restaurant just reopened that night and while the food was good the service was terrible. I had to ask 3 times for a drink. We also got a massage (couples) and it was $900. Was it worth it? Eh...I likely will book a diff hotel next time. If yo udo go make sure you are not on a high floor under the rooftop bar unless you think you want to be up all night.

Reviewed on Sep 22, 2025

Night Hotel Broadway

Night Hotel Broadway

2.5 out of 5
Manhattan
Price was $1,331, price is now $697 per person
$697
per person
Nov 12 - Nov 19
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7/10 Good! (2,403 reviews)
Loved the people their friendly and supportive it’s nice clean hotel area is quiet

Reviewed on Sep 27, 2025

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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
$71 nightly
The price is $82 total per night from Sep 30 to Oct 1
$82 total
Sep 30 - Oct 1
Total with taxes and fees
8/10 Very Good! (1,000 reviews)
Great Stay 👍 👌
"Clean place and the staff is friendly and helpful the prices are lower then other places in town"

Reviewed on Sep 21, 2025

MHO Hotel Bordentown
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
$110 nightly
The price is $126 total per night from Oct 5 to Oct 6
$126 total
Oct 5 - Oct 6
Total with taxes and fees
7.2/10 Good! (1,019 reviews)
"Everything was fine. I could not use my Hilton Honors Card because I booked through Expedia. I thought that was weird."

Reviewed on Sep 22, 2025

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
$152 nightly
The price is $174 total per night from Oct 5 to Oct 6
$174 total
Oct 5 - Oct 6
Total with taxes and fees
8.8/10 Excellent! (1,026 reviews)
"Hotel excellent"

Reviewed on Sep 21, 2025

Hyatt Regency Princeton
See all 437 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.

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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 $370 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.