Windsor Vacations from $326

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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.
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Price was $688, price is now $326 per person
$326
per person
Feb 5 - Feb 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
7.4/10 Good! (5,413 reviews)
The staff was very helpful and courteous. Housekeeping was excellent.

Reviewed on Dec 30, 2025

Topping Rose House

Topping Rose House

4.5 out of 5
Price was $1,701, price is now $783 per person
$783
per person
Feb 12 - Feb 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
9.2/10 Wonderful! (136 reviews)
Great rooms, staff and food

Reviewed on Sep 28, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was $1,056, price is now $497 per person
$497
per person
Mar 12 - Mar 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (2,346 reviews)
Fantastic stay!! The room was amazing, clean and spacious. We loved Mimi at the front desk! Very nice and super helpful. We will be staying again.

Reviewed on Dec 29, 2025

Hotel Seville Nomad, in the Unbound Collection by Hyatt

Hotel Seville Nomad, in the Unbound Collection by Hyatt

4.5 out of 5
Manhattan
Price was $1,149, price is now $569 per person
$569
per person
Mar 1 - Mar 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,184 reviews)
The room was very tidy and spacious enough for a person to stay. I stayed for 5 nights, house keeping was done very promptly and staffs felt all welcoming when entering/exiting the building. Have not tried breakfast but I highly recommend on staying at Seville Nomad 👍

Reviewed on Dec 27, 2025

Harpoon House

Harpoon House

3 out of 5
Price was $1,204, price is now $613 per person
$613
per person
Mar 18 - Mar 23
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
8.4/10 Very Good! (147 reviews)
We were looking for a quick overnight in the East End, and the Harpoon House exceeded our expectations in every way. The room was spacious (a suite!) and well-appointed, blending the charm of the original 1648 (!) building with modern amenities and furnishings. We didn't take advantage of the on-property restaurant (formerly Blu Mar), but the menu - by acclaimed chef Rocco DiSpirito - looked excellent, if a bit pricey. Location was ideal, within easy walking distance of all Main Street shops and restaurants, and less than a mile to the beach. And, although things were a bit quieter than in the height of summer - not a bad thing! - we loved being out there for the fall harvest season, with wineries and farms in full swing. All-in-all, our stay at the Harpoon House made for a perfect fall weekend in the Hamptons - highly recommended.

Reviewed on Oct 20, 2025

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What to do in Windsor

A temple that looks like it's out of a dream. Come and discover one of the best kept secrets of the region.

Explore the Hindu Temple a Spiritual Gem Near New York

$120
per adult
100% of travellers recommend
Explore the Hindu Temple a Spiritual Gem Near New York
See all activities in Windsor

Windsor Hotel Deals

DoubleTree by Hilton Princeton

DoubleTree by Hilton Princeton

4 out of 5
4355 US Highway 1 at Ridge Rd. Princeton NJ
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $98 total per night from Jan 1 to Jan 2
$98 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
8.2/10 Very Good! (1,007 reviews)
The swimming pool is great!

Reviewed on Dec 24, 2025

DoubleTree by Hilton Princeton
The Heldrich Hotel

The Heldrich Hotel

4 out of 5
10 Livingston Avenue New Brunswick NJ
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $150 total per night from Jan 18 to Jan 19
$150 total
Jan 18 - Jan 19, 2026
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
There wasn't breakfast

Reviewed on Dec 25, 2025

The Heldrich Hotel
Hyatt Regency New Brunswick

Hyatt Regency New Brunswick

3.5 out of 5
2 Albany St New Brunswick NJ
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $145 total per night from Jan 8 to Jan 9
$145 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
Great messed upbmy food but overall great

Reviewed on Dec 21, 2025

Hyatt Regency New Brunswick
See all 385 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 $326 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.