Windsor Vacations from $579
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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.
Stonybrook Motel & Lodge
$667
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Manchester (MHT)
7.6/10 Good! (1,002 reviews)
I had decent stay. Everything was working okay. Forget about breakfast. No indoor pool. There is No breakfast No pool period. Nobody in the office in the morning. There is no phone in the room to call the office either.
But it's better than camping I think.
It was lot cheaper than other greedy hotels around.
Reviewed on Aug 24, 2026
Attitash Mountain Village
$625
per person
Sep 29 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Manchester (MHT)
8.6/10 Excellent! (569 reviews)
Very nice condo. Must be very popular in the winter. Spacious room with a Murphy bed. Slept very good. Restaurant on side was not open but very friendly staff directed us to thing to see in the neighborhood and places to eat
Reviewed on Aug 20, 2026
The Shire Woodstock
$1,043
per person
Nov 11 - Nov 18
found 9 hours ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
8.8/10 Excellent! (978 reviews)
We enjoyed our stay very much. We found our stay to very quiet. The back of the property was so peaceful and relaxing sitting by the river, listening to the birds and the gurgling of the river as it moves along.
The room was comfortable with a fridge and freezer for snacks/fruit etc. I'd like to see another chair in the room so that 2 people can sit by the window and experience the
view although this wasn't a game changer.
Reviewed on Aug 27, 2026
Stay near popular Windsor attractions
Black Pond
Commune with nature and explore the great outdoors at Black Pond during your travels in Windsor.
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?
Windsor Hotel Deals
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
$128 nightly
$139 total
Aug 31 - Sep 1
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
"It was good!"
Reviewed on Aug 25, 2026
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
$97 nightly
$105 total
Sep 9 - Sep 10
Total with taxes and fees
Hideaway Inn Mt.Sunapee
1403 New Hampshire Rte 103 Newbury NH
Fully refundableReserve now, pay when you stay
$165 nightly
$179 total
Sep 21 - Sep 22
Total with taxes and fees
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 |
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Frequently asked questions
How much does a Windsor vacation package cost?
You'll find cheap prices from $579 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.
