Windsor Trips (flight + hotel)

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Top hotels in Windsor

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 P7,561 per night from Jul 7 to Jul 8
P7,561
P8,204 total
Jul 7 - Jul 8
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
"Nice hotel"

Reviewed on Jun 28, 2025

Best Western Plus Keene Hotel
Newport Motel
Newport Motel
2 out of 5
467 Sunapee St, Newport, NH
Fully refundableReserve now, pay when you stay
The price is P6,754 per night from Aug 4 to Aug 5
P6,754
P7,328 total
Aug 4 - Aug 5
includes taxes & fees
8.8/10 Excellent! (199 reviews)
"Room was very large and clean. Needed table under hanging ceiling lamp. Beds were very nice, comfortable with fresh clean linen. Older motel kept up with fresh paint.newer roof. Bushes out front needed pruning . Hanging plants along terrace would be more inviting."

Reviewed on Jun 30, 2025

Newport Motel
Hampton Inn & Suites Keene
Hampton Inn & Suites Keene
2.5 out of 5
126 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is P8,344 per night from Jul 13 to Jul 14
P8,344
P9,053 total
Jul 13 - Jul 14
includes taxes & fees
8.8/10 Excellent! (310 reviews)
"Clean, friendly, and good breakfast"

Reviewed on Jun 1, 2025

Hampton Inn & Suites Keene
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.

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.