Windsor Vacation Packages

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Your Windsor Vacation

Our vacation packages to Windsor provide endless opportunities to delve into new sights, sounds and smells. And with all of the travel arrangements taken care of, you can kick back and enjoy your city escape to the fullest. Eager to do a little sightseeing? Spend your days enjoying popular attractions such as Franklin Pierce Homestead during your trip to Windsor. No matter your travel plans or budget, putting together a tailored Windsor vacation is easy with Expedia.

Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Mountain Lodge at Okemo
The Shire Woodstock
Jackson Gore Village
Woodstock Inn & Resort
Mount Snow Grand Summit Resort

Ready to book your vacation to Windsor?

 

Choose your dates

Windsor Hotel Deals

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 CA $172 per night from Aug 13 to Aug 14
CA $172
CA $187 total
Aug 13 - Aug 14
includes taxes & fees
8.4/10 Very Good! (871 reviews)
"Is a very well cared for hotel and I enjoyed my stay and I’ve stayed there several times."

Reviewed on Aug. 5, 2025

Keene Elm City Hotel, Ascend Hotel Collection
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 CA $195 per night from Aug 24 to Aug 25
CA $195
CA $212 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
"Great place!"

Reviewed on Jul. 31, 2025

Best Western Plus Keene Hotel
Courtyard by Marriott Keene Downtown

Courtyard by Marriott Keene Downtown

3 out of 5
75 Railroad St, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $260 per night from Aug 7 to Aug 8
CA $260
CA $282 total
Aug 7 - Aug 8
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Property in good condition, clean, well located in Keene."

Reviewed on Aug. 1, 2025

Courtyard by Marriott Keene Downtown
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?
Offering great value package deals from CA $1,293 on Expedia, you'll be pleasantly surprised at how much a vacation to Windsor costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Windsor?
You're likely to find lower prices and greater availability in January, February and March. Browse our cheap Windsor vacation packages and you could score some great off-season deals.
How many days is enough for Windsor?
Generally, a handful of days is enough to tick off the main attractions during your Windsor vacation. But if you prefer to have more time to rest or go on day tours, consider extending your trip.
How to find the best Windsor package deals?
Begin your search for a Windsor package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Windsor package deal straight away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Windsor getaway off to a flying start.
Is it cheaper to book a Windsor vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging hotels and flights separately. Better still, you can customize your Windsor escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Windsor?
If you've got your Windsor travel dates confirmed, book as soon as you can to score some awesome deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for setting off on a whim.
How to plan a trip to Windsor?

  1. Choose when to get away: Check your calendar and get packing. Your preferred season and the activities on offer will also help you decide when to vacation in Windsor.
  2. Budget wisely: As well as the price of your hotel, you'll need to consider other expenses. These include transportation, food and flights. Also, put aside some extra funds for unexpected expenses that could arise during your trip to Windsor.
  3. Decide how long to go for: Now that you're more familiar with Windsor, you can figure out the perfect length of your vacation. Put together a draft itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customized Windsor vacation package.

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