Windsor Holidays

Photo by Ada Diez Mas
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    Better together

    Save up to €185 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Windsor

Price found within the past 48 hours. Click for updated prices.
Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
per person
3 Sept - 6 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8/10 Very Good! (2,054 reviews)
Great location and good customer service.Excellent location and easy access to the most landmarks in NYC.Clean and Comfort.

Reviewed on 6 Jul 2025

The Lombardy Hotel

The Lombardy Hotel

4 out of 5
Manhattan
per person
20 Aug - 23 Aug
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (1,098 reviews)
Beautifully appointed hotel in a great area close to Times Square and Central Park. Staff were nice and helpful, would definitely stay here again!

Reviewed on 9 Jul 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
per person
12 Sept - 15 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (2,103 reviews)
It is a very good hotel

Reviewed on 9 Jul 2025

Aloft New York Chelsea

Aloft New York Chelsea

3 out of 5
Manhattan
per person
20 Aug - 23 Aug
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (744 reviews)
Spacious, comfortable bed, great views from the upper floors. A desk would be nice though!

Reviewed on 11 Jul 2025

Interfaith 21

Interfaith 21

2 out of 5
Manhattan
per person
26 Sept - 29 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (14 reviews)
Hotel is cute and the vibe is great. But no elevators (my room was in the last floor) and bathrooms are in the hallway shared with other guests and I did not know that.

Reviewed on 10 Jul 2025

Top hotels in Windsor

Hyatt Regency Princeton
Hyatt Regency Princeton
4 out of 5
102 Carnegie Ctr, Princeton, NJ
Fully refundableReserve now, pay when you stay
The price is €140 per night from 25 Jul to 26 Jul
€140
25 Jul - 26 Jul
includes taxes & fees
8.6/10 Excellent! (1,013 reviews)
"great hotel highly recommended good price"

Reviewed on 9 Jul 2025

Hyatt Regency Princeton
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
The price is €107 per night from 21 Jul to 22 Jul
€107
21 Jul - 22 Jul
includes taxes & fees
7.2/10 Good! (1,000 reviews)
"Excellent hotel, great stuff, room, amenities, convenient location, easy parking"

Reviewed on 6 Jul 2025

Hilton East Brunswick Hotel & Executive Meeting Center
MHO Hotel Bordentown
MHO Hotel Bordentown
2 out of 5
187 US 130 and 206, Bordentown, NJ
Fully refundableReserve now, pay when you stay
The price is €63 per night from 16 Jul to 17 Jul
€63
16 Jul - 17 Jul
includes taxes & fees
7.8/10 Good! (1,002 reviews)
"It’s affordable and more convenient to access for shopping and restaurants"

Reviewed on 8 Jul 2025

MHO Hotel Bordentown
See all 428 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.

Frequently asked questions

How much does a Windsor holiday package cost?
You can snap up a holiday package to this top destination from €773 on Expedia. But how much your holiday 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?
January, February and March are the best times to look for cheap Windsor holiday packages. Opting to travel in less busy months means you'll typically find lower prices on hotels and flights.
How many days is enough for Windsor?
Typically, a handful of days is enough to explore the main sights during your Windsor holiday. But if you prefer to have some time to relax or go on day trips, think about extending your itinerary.
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 holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging flights and hotels separately. Better still, you can personalise 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 holiday 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. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to go to Windsor.
  2. Set your budget: Factor in costs like food, flights and transportation when working out how much to set aside for your trip to Windsor. Then, pick a property that fits your budget, whether that's an economical stay or a more luxurious getaway.
  3. Decide your trip length: Consider how long you'd like to spend exploring Windsor. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customised Windsor holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.