Windsor Vacations from $463

Book a Hotel + Flight or Car together to unlock savings

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.
Mountaineer Inn

Mountaineer Inn

2 out of 5
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
8.8/10 Excellent! (495 reviews)
It was a beautiful location...so quiet and peaceful The rooms to sit and enjoy were wonderful

Reviewed on Aug 9, 2025

Cold Spring Plymouth Resort

Cold Spring Plymouth Resort

3.5 out of 5
Save 100% on your flight
per person
Sep 23 - Sep 27
found 14 hours ago
Roundtrip flight included
Tampa (TPA) to Manchester (MHT)
9/10 Wonderful! (132 reviews)
Perfect place for a family vacation in New Hampshire

Reviewed on Aug 8, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
per person
Sep 12 - Sep 15
found 19 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
8.8/10 Excellent! (796 reviews)
the shire was super cute and perfect for the weekend!

Reviewed on Aug 9, 2025

White River Inn and Suites

White River Inn and Suites

2.5 out of 5
per person
Oct 3 - Oct 6
found 19 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Manchester (MHT)
7/10 Good! (1,004 reviews)
The daytime desk clerk is very rude!!

Reviewed on Aug 9, 2025

Riverside Hotel, Ascend Hotel Collection

Riverside Hotel, Ascend Hotel Collection

2.5 out of 5
per person
Sep 23 - Sep 27
found 14 hours ago
Roundtrip flight included
Tampa (TPA) to Manchester (MHT)
9.6/10 Exceptional! (585 reviews)
Lovely, and very peaceful stay nestled beside the Connecticut River

Reviewed on Aug 6, 2025

Don't see what you're looking for?
See all available trips from Columbus to Windsor
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Discover the most popular places to visit in Windsor

Eaton's Magic Morsel

Enjoy an outing to Eaton's Magic Morsel during your stay in Hillsboro. Discover the mountain views while you're in the area.

Eaton's Magic Morsel

Franklin Pierce Homestead

Learn about the local history of Hillsboro with a stop at Franklin Pierce Homestead. Discover the mountain views in this relaxing area.

Franklin Pierce Homestead

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
$125 nightly
The price is $136 total per night from Aug 18 to Aug 19
$136 total
Aug 18 - Aug 19
Total includes taxes and fees
8.4/10 Very Good! (873 reviews)
"Staff were friendly, room clean and comfortable"

Reviewed on Aug 7, 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
$149 nightly
The price is $162 total per night from Aug 14 to Aug 15
$162 total
Aug 14 - Aug 15
Total includes taxes and fees
8.2/10 Very Good! (1,002 reviews)
Attention to detail
"We were completely stunned with how wonderful this hotel was from top to bottom. The staff was very friendly and accommodating (they let us have a 1 hour late check out with no charge), the breakfast was fantastic (best I’d ever had in a hotel that offers it free), it was extremely clean, and the ..."

Reviewed on Aug 6, 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
$189 nightly
The price is $205 total per night from Aug 17 to Aug 18
$205 total
Aug 17 - Aug 18
Total includes taxes and fees
8.6/10 Excellent! (1,000 reviews)
"Property in good condition, clean, well located in Keene."

Reviewed on Aug 1, 2025

Courtyard by Marriott Keene Downtown
See all 458 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.

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Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from $463 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.