Windsor Vacations from $327
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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.
The Latest Windsor vacation packages
Price found within the past 48 hours. Click for updated prices.
Vikings Villages Resort
$954
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
10/10 Exceptional! (240 reviews)
Love our stay in Vikings. Staff was amazing and very attentive and helpful. The cabins were beautiful, clean and had everything we needed. Very recommended. Hope to go back in the future.
Reviewed on Oct 13, 2026
Presidential Mountain Resort
$858
per person
Dec 26 - Dec 30
found 8 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Manchester (MHT)
9.6/10 Exceptional! (304 reviews)
The cabins are fantastic. It was a cold morning so we didn't get to explore the property much but I would definitely stay there again.
Reviewed on Oct 13, 2026
Stay near popular Windsor attractions
Windsor Town Hall
Windsor Town Hall is just one of the places to see in Windsor, so why not enjoy the other things to explore during your travels?
Black Pond
Commune with nature and explore the great outdoors at Black Pond during your travels in Windsor.
Windsor Hotel Deals
Hideaway Inn Mt.Sunapee
1403 New Hampshire Rte 103 Newbury NH
Fully refundableReserve now, pay when you stay
$157 nightly
$170 total
Oct 14 - Oct 15
Total with taxes and fees
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
$142 nightly
$154 total
Nov 1 - Nov 2
Total with taxes and fees
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
$93 nightly
$101 total
Oct 25 - Oct 26
Total with taxes and fees
7/10 Good! (1,005 reviews)
"The location is very convenient, just across restaurants, target, groceries, near downtown, and close by outdoor locations like MT Monadnock at about 30 minutes drive. It’s an older hotel so no luxury here, however, very nice staff. I have a service dog and no problem with checking in which I always ..."
Reviewed on Oct 13, 2026
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.
Find the Best Windsor Vacation Packages
Windsor Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
More vacations you might like
Frequently asked questions
How much does a Windsor vacation package cost?
You'll find cheap prices from $327 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 lower prices and greater availability in October, November and December. Check out our cheap Windsor vacation packages and you could land some excellent off-season deals.
How many days is enough for Windsor?
The ideal length for your Windsor vacation depends on what you'd like to do. Typically, a handful of days to a week will give you time to visit all the leading sights and explore some hidden treasures 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.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
If you're anything like us, you love discovering new places but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Windsor trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
