Windsor Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

Find the Best Windsor Vacation Packages

Windsor Hotel Deals

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 ₩184,539 per night from Jul 14 to Jul 15
₩184,539
₩200,225 total
Jul 14 - Jul 15
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 Jul 6, 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 ₩153,691 per night from Jul 20 to Jul 21
₩153,691
₩166,755 total
Jul 20 - Jul 21
includes taxes & fees
8.2/10 Very Good! (854 reviews)
"All was good. The room, the breakfast are all very good."

Reviewed on Jul 7, 2025

Keene Elm City Hotel, Ascend Hotel Collection
Newport Motel
Newport Motel
2 out of 5
467 Sunapee St, Newport, NH
Fully refundableReserve now, pay when you stay
The price is ₩164,846 per night from Jul 14 to Jul 15
₩164,846
₩178,858 total
Jul 14 - Jul 15
includes taxes & fees
8.8/10 Excellent! (200 reviews)
"Easy check-in and check out customer service was excellent"

Reviewed on Jul 5, 2025

Newport Motel
See all 466 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 vacation 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 vacation 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 vacation packages and you could land some excellent off-season deals.
How many days is enough for Windsor?
The ideal length of your Windsor vacation 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 vacation as a package?
Expedia vacation 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 personalized Windsor vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation 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 vacation.
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 vacation 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.