Windsor Holidays

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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 hotels in Windsor

Lakefront Cabin in Beautiful, Quiet Location
Lakefront Cabin in Beautiful, Quiet Location
Windsor
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Lakefront Cabin in Beautiful, Quiet Location
Best Western Plus Keene Hotel
Best Western Plus Keene Hotel
3 out of 5
401 Winchester St, Keene, NH
Fully refundableReserve now, pay when you stay
The price is €124 per night from 13 Jul to 14 Jul
€124
13 Jul - 14 Jul
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"My Daughter And I Stayed 3 Days 4th Of July And Loved Pretty Much Everything!! Staff Were Great,Breakfast Wow Awesome, Indoor Pool,Beautiful Gazebo And Other Outdoor Lights!! Our Only Note*Rotate The Mattresses 1Side Of Bed Sinks,The Other Side Firm!! Tyvm 😁 😊 We Will Be Returning Soon!! Maureen ..."

Reviewed on 6 Jul 2025

Best Western Plus Keene Hotel
Keene Elm City Hotel, Ascend Hotel Collection
Keene Elm City Hotel, Ascend Hotel Collection
2.5 out of 5
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is €107 per night from 16 Jul to 17 Jul
€107
16 Jul - 17 Jul
includes taxes & fees
8.2/10 Very Good! (852 reviews)
Good room
"Good, clean room. Breakfast was decent, my family enjoyed the pool."

Reviewed on 30 Jun 2025

Keene Elm City Hotel, Ascend Hotel Collection
See all 452 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.

Popular places to visit

Eaton's Magic Morsel

Enjoy an outing to Eaton's Magic Morsel during your stay in Hillsboro. Discover the mountain views while you're in the area.

Eaton's Magic Morsel

Frequently asked questions

How much does a Windsor holiday package cost?
You'll find cheap prices on Expedia for your Windsor escape. However, factors like your choice of hotel, the season and length of stay will influence how much your holiday to Windsor costs.
What are the cheapest months to go to Windsor?
You're likely to find reduced prices and greater availability in January, February and March. Explore our cheap Windsor holiday packages and you could land some excellent off-season deals.
How many days is enough for Windsor?
The ideal length of your Windsor holiday depends on what you'd like to do. Usually, a few days to a week will give you enough time to check out all the top attractions and discover some hidden spots along the way.
How to find the best Windsor package deals?
Begin your search for a Windsor package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Windsor package deal right 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 escape underway.
Is it cheaper to book a Windsor holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component separately. And you'll still get the freedom to create a personalised Windsor holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Windsor?
Land incredible discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Windsor holiday.
How to plan a trip to Windsor?

  1. Choose when to travel: Check your calendar and get packing. Your preferred time of year and the type of activities on offer will also help you decide when to visit Windsor.
  2. Plan your budget wisely: In addition to the price of your hotel, you'll need to consider other expenses too. These include transportation, flights and food. Also, set aside some extra funds for unexpected costs that may come up during your trip to Windsor.
  3. Decide how many days away: Start by compiling a list of the activities and sights you'd like to get to in Windsor. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick a Windsor holiday package that brings all your bookings together.

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