Windsor Vacations from $319

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
Price was $378, price is now $319 per person
$319
per person
Nov 7 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
8.8/10 Excellent! (507 reviews)
Virtual check in/out was a very different experience.

Reviewed on Sep 25, 2025

The Grand at Bedford Village Inn

The Grand at Bedford Village Inn

5 out of 5
Save 100% on your flight
Price was $1,558, price is now $1,104 per person
$1,104
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Manchester (MHT)
9.6/10 Exceptional! (345 reviews)
Beautiful inn...very clean..very comfortable bed.

Reviewed on Sep 21, 2025

The Centennial

The Centennial

4 out of 5
Price was $817, price is now $579 per person
$579
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Manchester (MHT)
8.8/10 Excellent! (1,001 reviews)
Historic property with charm and charisma. Close to capitol and downtown shopping district.

Reviewed on Sep 24, 2025

Hampton Inn by Hilton Concord/Bow

Hampton Inn by Hilton Concord/Bow

2.5 out of 5
Price was $652, price is now $517 per person
$517
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Manchester (MHT)
8.6/10 Excellent! (1,006 reviews)
Tom at the front desk was very welcoming and thorough….breakfast nice….would stay again!

Reviewed on Sep 17, 2025

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Price was $581, price is now $489 per person
$489
per person
Oct 30 - Nov 3
found 14 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
8.8/10 Excellent! (223 reviews)
Great place to stay!

Reviewed on Sep 25, 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, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

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 Oct 5 to Oct 6
$136 total
Oct 5 - Oct 6
Total with taxes and fees
8.4/10 Very Good! (901 reviews)
"Wonderful stay very nice place comfortable bed."

Reviewed on Sep 18, 2025

Keene Elm City Hotel, an Ascend Collection Hotel
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road, Keene, NH
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $119 total per night from Sep 29 to Sep 30
$119 total
Sep 29 - Sep 30
Total with taxes and fees
7/10 Good! (1,006 reviews)
"A group of us come here every year and we never hesitate to come back. Not the Ritz, but perfectly fine and very reasonably priced to have access to a pretty nice part of NH."

Reviewed on Sep 20, 2025

Days Inn by Wyndham Keene NH
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 Sep 29 to Sep 30
$162 total
Sep 29 - Sep 30
Total with taxes and fees
8.2/10 Very Good! (1,014 reviews)
"It was quiet and the staff was friendly. Great and easy to get to location."

Reviewed on Sep 24, 2025

Best Western Plus Keene Hotel
See all 462 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 $319 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.